A Year of Villain Songs

 I've been engaged in a project, of sorts, for the past year. I was looking at a list of top "villain songs"--broadly defined as songs sung by or about a story's villain--and thought to myself, I could do better than that. And so I did. Every day, for 365 days, I've been posting one villain song, and a link to a video of it on Facebook. (I'm sure any subsequent drops in my friends is purely coincidental.) And, for the last half or so, I tweeted the links as well. For posterity's sake, I thought I'd post the list here. A few provisos:

1) This is a numbered list--to make sure I've got all 365 songs--but not an ordered list, because, frankly, finding 365 villain songs was enough work without creating some master rubric to evaluate them all. I burned through a lot of my favorite at the beginning when I wasn't sure how many I'd be doing. Beyond that, I tried to pick "special" ones for momentous numbers, generally at multiples of 25.  And the last ten or so are the best from my remaining pile.

2) Some of them have links, and some of them do not. This is largely because--see 1), making the list was enough work. They're mostly findable through a google search, if you're curious.

3) This list is not quite the order they were originally presented. I didn't keep great records of the whole list until I was fifty or so songs in, so that order's messed up a bit, and I'd do things like count 124 twice, and not notice till much later, then skip ahead accordingly. But it's close to the original order. Pardon the errors; I've marked the ones I've noticed. 

4) Favorite songs are marked with favorite.

5) There was a rather large number of songs that didn't make the 365 cut. For the most part, it's because I'm less familiar with them. If you've got something that you think should be added to the overall list, by all means, let me know and I'll put it in the extras.

Here we go, then.


1) "Where there's a whip, there's a way." animated Lord of the Rings.
2) "Money," Tom and Jerry: The Movie.
3) "Fett's Vette." MC Chris (favorite)
A lot of my affection for this one is probably because I first heard it while doing my initial Sealab 2021 jag.
4) "Gaston." Beauty and the Beast (favorite) 
Gaston is just so exuberant. Once he gets into things, anyway. When he was a lad, he ate six dozen eggs to help him get large!
5) "Still Alive." Portal (John Coulton) (favorite)
There's something about a passive aggressive AI working her passive aggressive disregard for human life into a song that really appeals to me.
6) "Slipping." Dr Horrible's Singalong Blog (favorite)
As a song, I prefer "On the Rise," but this one, I argue, is Billy at his most villainous. He's really getting a thrill out of seeing people afraid of him. 
7) "Yodle-Adle-Eedle-Idle Oo." Home on the Range.
God, this is a terrible song.
8) "Second Rate." Return of Jafar.
As someone mentioned at the time, this is the best thing about that movie. 
9) "Marley and Marley." Muppet X-Mas Carol. (favorite)
"Doomed, Scrooge! You're doomed for all time! / Your future is a horror story, written by your crimes!". Such a dark song for a Muppets movie.
10) "Hellfire." Hunchback of Notre Dame. (favorite)
You know, that song in a children's movie where a self-righteous man lusts after woman and decides he'll either have her or send her to hell.
11) "Chilly Down." Labyrinth. 
12) "We Hate the Sun." Rockadoodle.
13) "Petey's King of France." Mickey Mouse's Three Musketeers. (favorite)
I know it's just lyrics set up to the existing song, but I really like this song. It captures the angst at the core of Disney's most unsung villain. Thanks for getting all meta about it, turtle. 
14) "Oogie Boogie's Song."  Nightmare Before X-Mas.
15) "Prince Ali (reprise)." Aladdin. (favorite)
True story: I'd often sing the "adequate cause" bit to my little brother, with the accompanying nose grab and face slap. ...I wonder why he doesn't call me more.
16) "Goldfinger." From the James Bond movie, natch.
17) "Cruella de Ville." 101 Dalmatians.
18) "MODOK, MODOK."
19) "I Crush Everything." Jonathan Coulton. (favorite)
It took me ages to realize that this song was literally about a giant sea creature, rather than figuratively.
20) "Madness of Scar." Lion King: The Musical. 
21)  "Why Me." Aladdin. (Deleted song)
There's a few deleted Jafar songs that never made it to Aladdin. The world is the worse off for it.
22) "Scorpio." from The Simpsons. (favorite)
"Hammocks! Homer, there's four places. There's the Hammock Hut, that's on third."
"Uh-huh."
"There's Hammocks-R-Us, that's on third too. You've got Put-Your-Butt-Here."
"Mm-Hmm."
"That's on third. Swing Low, Sweet Chariot... Matter of fact, they're all in the same complex; it's the hammock complex on third.
"Oh, the hammock district!"
"That's right."
23) "Ra Ra Rasputin." Abba.
24) "In the Dark of the Night." Anastasia. (favorite)
I'd say this is widely considered the top non-Disney villain song, and there's a pretty good case for it.
25) "Come Little Children." Hocus Pocus. (favorite)
It's probably my most favorite thing that Sarah Jessica Parker has been associated with. 
26) "Cthulhu and Me." South Park. (favorite)
I still don't get Cthulhu and Cartman's relationship. It's a bit Totoro, a bit Iron Giant, and a bit Warner Bros cartoon.
27) "Don't Fall in Love." Beauty and the Beast: Enchanted Christmas.
The first of many really awful songs sung by Tim Curry. He's got some good ones too,  but a lot of absolute stinkers.
28) "The Mob." Beauty and the Beast. (favorite)
Gaston's second, but not final, appearance. "We don't like / what we don't understand / in fact it scares us." At least they're an honest mob, who know their own motivations.
29) "What You Feel Inside." Buffy. (favorite)
Hey, remember that time Xander raised a demon that killed people, and was never, ever held responsible for his deliberate actions? Good times, good times. Ok, seriously, I like the way the villain here gets so caught up in his routine he basically forgets Dawn is there.
30) "The World's Greatest Criminal Mind." The Great Mouse Detective.
Notable for having Moriarty voiced by Vincent Price.
31) "Scrooge." A Muppet's Christmas Carol. (favorite)
"When a cold wind comes, it chills you, chills you to the bone." / "But there's nothing in nature that freezes the heart like years of living alone." / "It paints you with indifference, like a lady paints with rouge." / "And the worst of the worst--the most hated and cursed--is the one that we call Scrooge." Bless you, Muppets.
32) "Yo Ho (A Pirate's Life for Me)." Pirates of the Caribbean. 
33) "Oogie Boogie" (reprise). Oogie Boogie (videogame). (favorite)
This one gets favorite rather than the original because I really like how they transform it into a duet between Oogie and Jack.
34) "My Lullaby." Lion King II.
Disney straight-to-video sequels are a very mixed bag when it comes to the songs. This might be the best of the lot.
35) "Skullcrusher Mountain." Jonathan Coulton.
36) "Don Karnage." Tail Spin.
There's a lot of weird things about Tail Spin (let's take the Jungle Book characters and translate them into a psuedo-1930s art deco world with Rocketeer-esque sky-pirates) but Don Karnage, a swashbuckling sky-pirate with Ricky Rickardo's accent is definitely up there. 
37) "Almost Human." Voltaire.
Voltaire's made a career out of doing creepy, gothic type songs that can still poke fun at their excessive gothiness. I respect that.
38) "Wonderful Toys." Batman musical.
Just before I hit 340, I realized I accidentally skipped 38. Rather than renumber everything else, I slipped it in. Still, it fits with what's going to be starting in 41.
39) "Headless Horseman." Legend of Sleepy Hollow.
I hope there's a Sleepy Hollow TV show  clip to this song somewhere.
40) "Kidnap the Santa Claus." Nightmare Before X-Mas
Like "Oogie Boogie Man," it's not a bad song, but my Nightmare Before X-Mas favorites aren't the villain stuff--it's "This is Halloween," "Jack's Lament," "What's This."
41) "The Riddler." Frank Gorshin.  Batman series.
This marked the start of November 2013, aka month of Batman villains. Gorshin's Riddler laugh is pure excellence. Sadly, it's not quite enough of an actual song to make it a favorite.
42) "Little Birdy." Evil Ebenezer.
Evil Ebenezer made an entire album of songs about the Penguin. They're... not my taste, but I appreciate the effort.
43) "Drives Us Bats." Batman: Brave and the Bold.
Neil Patrick Harris--he's going to keep appearing on this list--starred as "The Music Meister" in a musical episode of the Batman cartoon. And he sings in all of the songs, so they're all de facto villain songs. They're all reasonably good, though the first and last are my favorites. 
44) "Bat Romance." Bad Romance parody with female Bat-villains.
45) "Mr Freeze." Slayer.
Ok, so I don't know of any evidence that this song refers to Batman's Mr Freeze, but whoever this guy is, he's villain enough.
46) "Setting the Woods on Fire."  The Batman.  (favorite)
So many versions of Harley Quinn and the Joker frame it as if Harley's in an abusive relationship. It's nice to see a version where they're both just smitten with each other. I mean, still villainous crazy people, but relationship-wise, much healthier.
47) "Bane Song." George K. Value.
48) "Mr Freeze." Batman and Robin.
Fan video that goes full-Schwarzenegger Mr Freeze. Weirdly catchy.
49) "The Joker is Wild." Jan & Jean.
Kind of a Beach Boys' version of the Joker. 
50) "Riddler." Method Man.
Remember that time Method Man did a rap video for Batman Forever? Well, you do now.
51) "Joker's Song." Miracle of Sound. (favorite)
Miracle of Sound's done a few villain songs; not all made it to the main list. This starts slow, but builds really nicely. Not quite my favorite Joker song, but good.
52) "Grand Order of Occidental Nighthawks." Evil Ebenezer.
53) "Poison Ivy." Me'Shell Ndegeocello. Written for the Batman & Robin movie.
54) "I Kinda Like These Criminals." NAMTAB Project.
In the Evil Ebenezer vein, NAMTAB Project is an album from the POV of Ra's Al Ghul. So... yeah.  I think he ties with Mr Freeze as "Batman's Enemies Least Likely to Burst into Song."
55) "The Music Meister." Batman: Brave and the Bold. (favorite)
This is the first song of the set. I particularly like how it presents Music Meister's origin to four lines--two, if you make a little jump. "The bullies used to pick on me because I sang in choir / But something very strange occurred when I kept singing higher! / The ruffians around me quickly fell into a trance / and it was then with wicked glee I made those puppets dance!" If only every villain could be lyrically distilled so purely.
56) "Demon's Head." NAMTAB Project.
57) Catwoman's Song. Batman: The Musical. 
Not to be confused with the other Batman musical, Holy Musical, Batman.
58) "Mr. Freeze." K's Choice.
Again, any actual resemblance to the Batman character may be coincidental. But the alternative is that they're singing about the metaphoric embodiment of their own desire to suppress their emotions, which is also very villainous, if you think about it.
59) "Say We're Sweethearts Again." Harley Quinn from Batman: Animated Series.
60)  "The Capture" by Penguin.
This is a two-parter sung by the actor from the live tv version, I think. The second part follows.
61) "The Escape." by Penguin.
62) "Killing Joke."  Fans singing the lyrics from the comic of the same name, Batman: The Killing Joke. (favorite)
I like the harmony on "loony." It's simpler than Miracle of Song's Joker song, but I think I like it a little better for that.
63) "One Bad Day." Bobaflex's Tales from Dirt Town.
Other interpretation of Batman: The Killing Joke. It's another pretty good Joker song, but not quite as catchy to me.  I really like the chorus, though.
64)  "Where's The Fun in That?" Batman: Brave and the Bold. Joker again.
I think this song does a great job of capturing the Joker's credo (especially in the Brave and the Bold version), but again, not quite catchy enough. As for the clip, the context is that Joker's temporarily got Bat-Mite's powers--it's meant to be an adaptation of the Emperor Joker comicbook storyline. I like the flapper version of Harley Quinn, and it's still kind of shocking to see Batman get killed multiple times in the episode.
65) "Catwoman." Anastasia Creed. For the movie Catwoman.
66) "I Can Beat Him Up." Paniks.
In which the speaker confidently declares he could totally take Batman.
67) "Death Trap." Batman: The Brave and the Bold.
Another entry from the Music Meister episode.
68) "Somewhere Bat-Free." Fan parody at 2004 ComiCon.
69) "Rogues Are We." Holy Musical Batman.
And we finish the Villains of Batman month with a rare ensemble villain piece.
70) "Ruber." Quest for Camelot.
This is a truly awful song.
71) "See My Vest." Mr Burns from The Simpsons. (favorite)
"I really like the vest!"
"I gathered, yeah."
72) "The Hounds." The Protomen. (favorite)
A song from a rock opera version of Megaman. This, from what I understand, is Dr Wiley choosing to betray humanity for the first time. It's a really, really good song. Not a lot of villain songs with a bit of swing to them. 
73) "I'm Mean." Bluto from Popeye.
I enjoy the lyrical simplicity of this one. It takes a certain courage to rhyme "I'm mean" with "know what I mean."
74) "Eggs." Land Before Time II.
There's at least two other Land Before Time villain songs. This, sadly, is probably the best one.
75) "Dance, Magic, Dance." Labyrinth.
76) "Singing in the Rain." Clockwork Orange.
77)  "I Wanna Be Evil." Eartha Kitt.  (favorite)
Thanks to Emperor's New Groove, Kitt is going to be making a few appearances. This is probably the best one.
78) "Guys Like Potter." A Very Potter Sequel, featuring Lucius and Snape.
There's going to be a few entries from the Potter musical series. The first Harry Potter musical doesn't have a Snape song at all, which--what's even the point? This one goes straight out to the friend zone villain, and is notable for containing the immortal lines: "So many assholes in this place! So many assholes in my face! Ah, the golden years of high school."
79) "Top of the Woods." Hoodwinked. 
It's Andy Dick singing. I mean, that's pretty villainous right there.
80) "Forever Yours." Once On This Island. 
Maybe not strictly a villain song, since the heroine has a fairly large part,  But the "your life is mine" sentiment definitely fits. Plus, that kid has a nice evil laugh going.
81) "Greed is Good."  Leeman BrothaZ. Parody rap on bankers.
82)  "Epiphany." Sweeney Todd.
Almost all of the songs from Sweeney Todd are villain songs--and we'll be seeing more of them--but I picked this one first as the moment where Todd just kind of gives in to the darkness.
83) "No More Mr Nice Guy." The Swan Princess.
84) "El Dorado." Iron Maiden.
85) "Scrooge vs Grinch." Epic Rap Battles.
This began my December Christmas villain kick. It's not a month long, thankfully.
86) "I Hate Santa Clause." Rudolph: The Movie.
87) "Snow Miser, Heat Miser." Year Without Christmas.
88) "Snow Miser, Heat Miser." Year Without Christmas: Live Action.
I know it's the same song as the other version, but the production is very different. The scantily clad women are unnecessary, but I do like the over-the-top, scenery-chewing performances. For the romantics in the crowd, the research here turned up a sequel to Year Without Christmas in which the two brothers reconcile and sing the exact damn song again, except declare each other to be "too much" instead of themselves at the end. I guess it's a compliment?
89) "Father Christmas." Scrooge: The Musical.
90) "Santa Claus is Gunning You Down." Futurama. 
91) "Christmas Demolition." Edd's World.
92) "You're a Mean One, Mr. Grinch." (favorite)
How can you not love this song? "You've got garlic in your soul."
93) "Lobe's Song." Freakazoid.
94) "Intelligence." Help, I'm a Fish.
It's not a good song, but almost worth it to hear Alan Rickman sing as fish.
95) "Wasting Away." Little Mermaid  Musical.
96) "Phantom of the Opera." Phantom of the Opera. (favorite)
I love the chorus for this one. Again, there's a few villainous PotO songs, but this is clearly the big one. 
97) "Blood of Angels." Brown Bird.
98) "Gnorgia, The Queen of Mean." A Troll in Central Park.
99) "What's Up Duloc." Shrek: The Musical.
It says more about me than I want people to know that out of all the characters in Shrek, I empathize the most with Farquad. 
100) "Worst is Yet to Come." Babes in Toyland.
I'm only realizing in retrospect that this isn't an auspicious choice for #100. Plus, not a great song. I do like how the villains convince themselves they should be scared part way through scaring the kids.  They really should have had a better exit strategy.
101) "Maison de Lunes." Beauty and the Beast Musical
102) "The Anarchist."  Rush.
103) "Don't Make Me Laugh." The Pebble and the Penguin.
It's not as bad as Rueber, but there's still something weird and off about this one.
104) "King of Wonderland." Care Bears.
The song starts off in a "villain wants to impose order on fantasy"/Farquad kind of vein, but that lightning shot at the end is pure "villain wants to give kid viewers nightmares."
105) "Mine." Elmo. (favorite)
Why is it a favorite? It's Mandy Patinkin singing. That's why.
106) "Malachis." Happy Days musical.
107) "Hey There Cthulhu." Eben Brooks.
While it lacks the complexity of South Park's "Cthulhu and Me," a "Hey There Delilah" parody starring Cthulhu appeals.
108) "Just Say Yes."  Secret of Nimh 2.
The Secret of Nimh holds a special place in my childhood nightmares, thanks to the early chaotic lab scene. This film is a pale imitation of the original,  and the sound quality here is terrible, but I appreciate how much Martin Brisby goes full bonkers--probably helps that he's voiced by Eric Idle.
109) "Junkyard Society." Lady and the Tramp 2.
110) "A Freak Like Me." Spider-Man: Turn Off the Dark
111) "Let It Go." Frozen. (favorite)
All right, not really a villain song, but it was back in January, I'd just seen the film for the first time, and she could sort of become a villain if the plot had gone a littler differently, and I like the song so very, very much. As I put in the original post, if you don't like it, you can make your own list of songs I put in my villain list that aren't really villain songs and I'll listen to it, because it means I'll get to listen to Let It Go again.
112) "When You're Big." Land Before Time 2.
113) "Who Is The Boss." Felix the Cat. 
Some of the more obscure cartoon villain songs offer these weird glimpses into non-Disney visions of animation.
114) "The Master's Song." Renfield from Dracula: The Musical.
The first of many Dracula-related songs.
115) Gollum's Song.  Emiliana Torrini. (favorite)
I love everything about this song--there's something just so right about Gollum's inner turmoil being voiced by Torrini--but I especially love the way it segues into the main Lord of the Rings theme at the end. "This, too, is part of the whole."
116) "It Will All Be Mine." Giovanni from the Pokemon Musical.
Surprisingly catchy.
117) "Intruder." Peter Gabriel.
118) "Welcome to the Forty Thieves." Aladdin and the King of Thieves. 
The second direct-to-video Aladdin movie has two villain songs--and they're not too bad.
119) "We're the Titans." Xena and Hercules. 
So for some reason, it was thought to be a good idea to do an animated Xena and Hercules crossover. I guess it makes the Titans a lot easier, special effect-wise.
120) "Oswald." Evil Ebenezer.
I thought I'd finish up the album, even though Batman month was over, so there's more Evil Ebenezer to come. 
121) ""This Jesus Must Die." Jesus Christ Superstar: The Movie.
The movie decided to go a sci-fi direction, I guess? I prefer Herod's number, as far as villain songs go (it's a little catchier) but this has an impressively crazy weirdness to it.
122) "What is Christmas?" The Lost Christmas musical.. 
123) "Toxic Love." Ferngully. (favorite)
The original is really one of Tim Curry's better efforts--the smarmy, oozing nature of Hexxus plays to his strength. But for my money, a female cover is just a much more interesting take on it. 
124) "We're Despicable." Mr Magoo special.
125) "Slick." Matthew Patel from Scott Pilgrim
126) Shark Songs. Jaws.
So the idea here is that the author took footage from Jaws, and rejigged the audio and added a voiceover to make it the heartwarming tale of a man and his singing shark. I think I added it to the list as a compromise--I wanted the Jaws theme, but I had a no instrumental only rule (gotta be singing in my songs!) and this was the closest I could get. Court the controversy!
127) "Like Father Like Son." Aida.
The story here is that Aida is a musical Elton John wrote with Tim Rice, based on a German opera by the same name, all about ancient Egypt. The evil vizier Zozer (is there ever a vizier that isn't evil?), here, is trying to convince his son to give up that Aida girl and get back to the "take over Egypt" plan. Mostly, I remember this song because I wrote down the name but not the name of the musical, and I had a devil of a time finding it again.
128) "Where in the World is Carmen Sandiego?" (favorite)
Best A Capella villain song? Could be. Could be.
129) "Night and a Day." Pepe Deleuxe's Queen of the Waves.
130) "I M Meen."
Another rare videogame villain song. Someone in the comments said that Meen has a real pedophile vibe based on the way he takes the girl's ribbon at 0:50, and well, no none of us can unsee that.
131) "Adolf Hitler vs Darth Vader 2." Epic Rap Battles of History.
132) "Vanessa Finished." The Little Mermaid.
133) "Crooked Man." Babes in Toyland.
Much better song than "Worst is Yet to Come," though I'm fond of that one too.
134) "The Elegant Captain Hook." Peter Pan.
135) "Angel of Death." Slayer.
136) "Happy Evil Love Song." Phineas & Ferb. (favorite)
Not enough evil love songs. 
137) "All Good Things Must End." Ursula's song, cut from The Little Mermaid Musical.
138) "Ballad of Farquaad." Farquaad, in Shrek: The Musical.
139) "Dracula's Lament." Forgetting Sarah Marshall.
Not to be confused with Dracula: The Musical. This is the one with Jason Segel and a puppet. 
140) "I Hate People!" Scrooge: The Musical.
Not to be confused with the musical versions with Muppets.
141) "Gonna Get My Wish." Little Mermaid II.
Now, this would be an example of how made-for-video Disney sequel villain songs go wrong. 
142) "Humiliate the Boy." Jafar. Deleted song from Aladdin. 
143) "Captain Gutt." Ice Age 4. (favorite)
I wouldn't have expected anything from a villain song for a fourth movie in a series, but the sea shanty tune works for me; and Peter Dinklage brings a lot to the role. He should sing more. (Also: This was the highest grossing animated film of 2012! Peter Dinklage or no, that shouldn't be. And with Madagascar 3 in the number two slot, and Brave and Wreck-It-Ralph far below. We don't deserve nice things.)
144) "All is Dark." Dracula: The Musical.
145) "Stars." Les Miserables' Javert.
146) "Electric Eye." Judas Priest.
147) "It;s Our House Now." Collective Disney villains in Mickey's House of Villains.
Disappointing, all in all. That many villains formerly involved in good songs should be a good song. But I suppose no one's going to break the budget for a production like this.
148) "How Bad Can I Be." The Lorax.
Answer: Very. And yet...this song is a terrible earworm. "How baaaaaaaad can I be? I'm just helpin' the economy. How ba-a-a-a-ad can I be? I'm just doin' what comes naturally."
149) "Half Bird Half Man." Evil Ebenezer.
150) "Poor Unfortunate Souls." The Little Mermaid. (favorite)
And after all that teasing with sequels, musicals, and deleted songs, I finally posted Ursala's big number. It's maybe the quintessential villain song--bar one, anyway. 
151) "Witch's Egg." The Forbidden Zone.
A really weird song from a really weird movie.
152) "I Believe in Harvey Dent." Adam Warrock.
I've got a lot of admiration for Warrrock's geeky songs. I wish I got a chance to use more of his villain songs, but I saved them for too long, and couldn't justify putting more than one in final set. C'est la vie. At least I got a few in the main list.
153) "Club Villain." Your Favorite Martian.
154) "Slaughter Your World." Looking for Group.
Not a lot of villain songs based on webcomic characters.
155) "Who Needs You?" Land Before Time
I told you there were worse Land Before Time villain songs down the line.
156) "My Name is Mok." Rock and Rule..
A lot of people are nostalgic for the Rock and Rule, an animated sci-fi rock-opera. I don't see it myself, but...
157) "Only You." Joker in the videogame Batman: Arkham Asylum.
158) "Wooly Bully." Freddy's Greatest Hits.
There's a whole album of songs from the original actor. 
159) "EGGMAN." Sonic Adventure 2.
160) "We're the Wickersham Brothers." Horton Hears a Who. (favorite)
Not as well known as the Grinch, but it's another Chuck Jones-voiced song, so you can't go wrong with that.
161) "Shadow Man." Bayou Boogie. 
If there's one thing I have against The Princess and the Frog, it's that it doesn't have much of a villain song. The chorus is basically just "I've got friends on the other side," which is a far cry from that of "Poor Unfortunate Souls" or "Hellfire." And it's a shame, because I *love* Keith David as a voice actor--Gargoyles is a 90s masterpiece of animated storytelling, and it all comes out of him as the lead. Enter Bayou Boogie: a CD of songs "inspired" by the original movie. A whole new chance to get a good Keith David song.  But Disney has been very active in taking down any youtube versions of the album. Took me ages to find this link. And the song *still* isn't very good. At least it's a better chorus. Maybe the problem is me putting my own expectations on the songs; they've all got this upbeat jazz bit, which someone obviously thinks fits the character. But I like my villain songs more sinister, in general. Another song on the album, "Do What I Wanna Do" is much the same. "Love is a Magical Mystery" gets closer, but it's not really a villain song.
162) "Despicable Me." Despicable Me. Pharrell Williams.
163) "Elm Street Dreams."  Freddy's Greatest Hits.
164) "King Herod's Song." Jesus Christ: Superstar The Movie.
Honorable mention goes to Christo Graham's Muppet/Jesus Christ's mash-up Muppet Christ Superstar, casting Rawlf the Dog as Herod. (It's on the the extras list, but I wanted to get it out there.)
165) "Dr Steel." Dr Steel.
Like Evil Ebenezer, Dr Steel used a villain conceit to construct songs, but instead of an album, he based his entire stage persona of a villain of his own creation. It's impressive, though I don't really care for the songs.
166) "Trust in Me." Kaa, in The Jungle Book.
167) "Ronery." Team America.
168) "Seven Deadly Virtues." Camelot: The Musical.
169) "Donkey Town." Dr Steel.
170) "Snuff Out the Sun." Emperor's New Groove.
It's almost criminal to get Eartha Kitt to voice a character, Sting to write the song, and then cut it out. Like the Princess and the Frog songs, it's more breezy than I like my Disney villain songs, but it grows on me, and gets better as it goes on. And that "Snuff Out the Light" chorus works.
171) "Arsenic Cake." Asterix and Cleopatra.
I like the comedy routine here, where the stupider villain can't seem to get a grip on the whole "murder ingredient" thing.
172) "Cold Inside." Evil Ebenezer.
173) "Easy Street." From Annie.
174) "Dr Octopus." Rock Reflections of a Super Hero. 
Spider-Man musicals before they were cool. Or before they flopped horribly, anway. It''s... definitely a piece of the 70s. Do check out the Stanley Lee spoken bridge at around 1:30. In comparison to DC villains (especially the Bat folk), the Spider-Villains don't get much love, so it's nice to see this. And of course it'd be Chris Sims that uploads it to the world.
175) "What do We Care." Feral Cat Pack in Tom and Jerry: The Movie.
176) "Face to Face." Catwoman song by Siouxsie and the Banshees for Batman: Returns.
177) "Chow Down." Hyenas' song from Lion King: The Musical.
178) "Drop Da Bomb."   Dr Steel.
179) "Mess With Me." Ursala, for the Little Mermaid animated TV series.
I think the quality here comes from using the original voice actor. She really knows how to convey the role. 
180) "Nigel Song." Rio.
It's an old school "villain brags" villain song, by Jemaine Clement, and the song's pretty clever. Can't say I'm ever going to watch Rio, though.
181) "Solomon Grundy." Batman. 
Maybe not strictly the Batman version, or strictly villainy, depending on your perspective, but at this point, I just wanted to hear a different Batman villain for a bit. 
182) "Master of the House." Les Miserables.
183) "Join Us." Evil Dead: The Musical.
I'd watch that. With the Walking Dead musical, there's a whole zombie subgenre to explore. 
184) "The Real Ludmilla." Bartok the Magnificent.
The first time I saw this, I was suitably impressed; I thought it was depicting Ludmilla, a conventionally attractive if obviously evil woman, giving up her beauty because, damn it, she wanted to be a dragon. Sadly, upon learning the context, it looks like she was expecting a different outcome. (Also, I couldn't stand Bartok. Never been a fan of the comic relief characters in children's cartoons.)
185) "Biggering." The Lorax. Deleted song.
It's a better song than "How Bad Can I Be" (and you can see traces of it in the latter) but it doesn't fit the tone of the movie as well, so I can see why they dropped it.
186) "In the Land of the Pigs." Batman: The Musical. (favorite)
 Not to be confused with Holy Musical, Batman!; this is a version commissioned by Jim Steinman that fell through. Not sure who this villain is meant to be (Joker seems a safe bet), but the song itself is clearly villain-intended. Got a nice epic quality to it. 
187) "I Can Change." Saddam Hussein, South Park: The Movie.
188) "Build the Robots." Dr Steel.
189) "Are you in or out?". Aladdin and the Forty Thieves.
190) "That's What It Takes to Rule." The Princess and the Pea.
191) "Nursery Rhymes."  Harley Quinn in the videogame Arkham City.
Keep in mind that I did an entire MONTH of Batman villain songs, and I'm STILL doing villain songs about them. Something about the Batman villains really hit the right note. (Pun not intended.)
192) "Doe-Me-Doe Duds." 5000 Fingers of Dr T. 
I love that Dr Seuss did a musical. I really have to watch this some day. 
193)"Dentist." Little Shop of Horrors.
This was a late series retcon. I didn't realize until I was typing out this list that I had skipped 193 (much like 38) and I had to insert it in at the very end--the day after Villain song 363, if I recall. Just as well; this is a pretty classic villain song, and it'd be a shame to leave it out. I mean, it's Steve Martin, singing.
194) "Prince Charmless." The Secret of Anastasia.
This isn't a great song, and it's in what probably isn't a great movie. But I've got a strange fascination for these second rate villain songs. They can be... playful, I guess? Because everyone involved knows they're not trying to do something great, so they're free to really camp things up. 
195) "Deranged." Batman's The Joker. Coheed and Cambria.
ANOTHER Bat villain song! Really, we should be doing shots. It's essentially a song about Joker and Batman, though personally, when it comes to the Joker's motivation, I prefer "Where's the Fun in That?". It's more Joker-centric, and Batman's relation is implied, rather than overstated. I guess I like a Joker that's revelling in his own thing rather than obsessed with Batman specifically. 
196) ""Happy Song." Mr Scratch from Alan Wake: American Nightmare.
What a strange little series. I'm glad Remedy (the company that makes the Alan Wake games) got the chance to flesh things out a little, even if the main game didn't do as well as they'd hoped.
197)  "Lament for a Toy Factory."  Dr Steel.
198) "Gay Purr-ee." Money Cat.
It's a shame the video version of this one doesn't exist any longer, because man, it was a perfect example of how creepy and strange animation used to be.
199) "Cell Block Tango." Chicago.
200) "Spell Block Tango." Todrick Hall. (favorite)
I think this was the song on the list that was most frequently suggested to me. And there's obviously a lot to love--the Cell Block Tango parody, the spot-on Disney villains, the pretty good lyrics, the retelling of Disney stories. I love the addition of Scar to the overall line-up, and a clearly insane  Red Queen is a cool idea, but my favorite of the bunch is Cruella. Lady isn't there because her man did her wrong--she's there because she got tired of her incompetent henchmen. I think a lot of villains can relate. 
201) "Choose Your Poison." The Return of Captain Invincible.
This movie starts Christopher Lee as the villain. It's another that I really should see.
202) "Conviction Yaxamandu." Tohou.
203) "Ode to Revenge." Dr Steel.
204) "You Gotta Love It." Swan Princess 2.
This is another example of the campy b-animated film. (Although to give it its due, the animation is head and shoulders an improvement on the Princess and the Pea.) I mean, the Swan Princess movie is obscure. Swan Princess 2 is a whole 'nother level. And this is one of the more rockin' all ages villain songs.
205) "Praise Be to Decepticon." Jam Project's song featuring the Transformer villains.
206) "Evil Midnight." The Return of Captain Invincible. 
207) Bibi Love's Song. Dead Rising 2 (videogame).
Some context: Dead Rising 2 is a Romero zombie pastiche game, and Love is meant to represent the over-the-hill Casino diva. Usually, in the Dead Rising formula, any character that`s slightly ridiculous snaps during a zombie outbreak and becomes a pyschopath you have to fight. I liked that Bibi Love is set up as such a fight, but then turns out to be someone you rescue. I've got a soft spot for her, just for that. 
208) Darth Vader vs. Adolf Hitler 3. Epic Rap Battles of History.
209) "Slapped by Moe." Dr Steel.
210) "Very Important Creature." Land Before Time VII.
Seven Land Before Time movies. SEVEN. Sometimes, mediocrity never dies. 
211) "Carnage Rules." Spider-Man's Carnage, by Green Jelly.
A (compared to Batman) rare Spider-Man villain song. 
212) "The Rap." From Leprechaun in the Hood. 
213) "King of the Creatures." Conroy Bumpbus. Song from videogame Sam and Max: Hit the Road.
214) "Atomic Superstar." Dr Steel.
215) "Mean Green Mother from Outer space." :Little Pet Shop of Horror.
Another late edition. Counting is hard, people.
216) "When You're Evil."  Voltaire.
217) "Freeze Ray." Dr Horrible's Sing-A-Long Blog. (favorite)
"Slipping" is a better villain song (as is the final song, and "Brand New Day") and "On the Rise" I like better as a song,  But "Freeze Ray" is probably best at conveying the dorky, insecure part of Billy.
218) "Death to Squishies." Courtney Gears from the videogame Ratchet & Clank: Up Your Arsenal.
I suppose it's not a big surprise that a game whose creators think "Up Your Arsenal" constitutes humor would include a parody character based on Britney Spears.
219) "Godzilla." Blue Oyster.
220) "Who Will I Kill." Mystery Science Theatre 3000.
Never got into this series; I feel like I missed the window in my undergrad when it would appeal to me the most. Plus, grammar pendant: "Whom Will I Kill."
221) "Just Like Me." Little Mermaid TV show.
Another less than excellent Tim Curry-sung song.
222) "The Moon Rises." Phonyphonic.
Given the devotion of its fandom, it's probably not surprising that My Little Pony has its fair share of fans who make fan-relevant songs--and there are some decent villain songs among them, too. I'm also a fan of Princess Twilight, so... (and, for the record, I don't consider myself a brony. I like the show, but not that much.)
223) "The Greedy." Raggedy Ann and Andy: The Movie.
Another example of how weird pre-90s animation was, before Disney drowned out the other voices.  
224) "Grimm." From American McGee's Grimm (videogame).
I'll be honest--American McGee's stuff has never really appealed to me. The Alice games are essentially platformer/shooters, in an engine that was never really great at the platforming part (especially for the first game). The gothic aesthetic is interesting, but a little of it goes a long way. I think that's why I preferred the more restrained depiction of Victorian London in the sequel game than the actual Wonderland. 
225) "Evil Night Tonight." Jill Tracy. (favorite)
I know what I said about jazzy-like villain songs earlier with The Princess and the Frog, but this one works for me. (It's also possible that I don't understand what jazzy means.) I think it's the smoky voice of the lead. I should have featured more Tracy songs; more songs of hers would qualify as villainous, I think.
226) "It Feels So Good To Be So Bad."  All Dogs Go To Heaven 2.
Every now and then, you get a villain song that really hits the basic notes: "evil is awesome," here's my evil plan." If he added more of "here's why I'm evil," you'd have the full trifecta.
227) "Be Prepared." Nightmare Moon from My Little Pony.
So if you're keeping track, this is a fan pretending to be Nightmare Moon covering the Lion King villain song. Never change, fandom. I do appreciate the new lyrics.
228) "Exterminate, Regenerate." Dr Who Dalek villain song.
Not a lot of Dr Who villain songs; I guess the fans just don't think that way. But I like the way this one brings out the sense that the Doctor is similar to the things he hates, right there in the title. 
229) Drill-X's songs, from the videogame Skylanders. 
230) "Where Evil Grows."  Poppy Family.
This group's probably best known for their big hit, "Where Are You Goin', Billy?".
231) "Things are not what they appear." Pocahantas 2.
232) "Get the Money." The Beagle Boys from DuckTales. 
Duck Tales was a big part of my childhood TV, so I'm glad of this song's existence. The Beagle Boys were always the least of Scrooge's rogue gallery (and how cool is that, that a character who's not remotely a superhero has his own rogue gallery?), but they were also the most determined.
233) "Make That Money." Alice Cooper.
234) "Misa's Song." Death Note. 
235) "Help Me Help You," The Mad Doctor from the videogame Epic Mickey. 
236) "Villain." Theory of a Deadman.
It was starting to be a pain to find an official version of this, so here's one associated with the villain from the Resident Evil games. ...There's a definite similarity between this and Bobaflex's One Bad Day, isn't there?
237) "Playing with the Big Boys Now." Prince of Egypt.
Not my favorite (I never saw the film, so the context isn't really there for me--although listening to it now, it's really growing on me) but it often places highly on Villain Song lists. 
238) "As the World Falls Down." Labyrinth. 
The sequel to Labyrinth was recently announced. I wonder what the tone will be, now that it'll (probably) have a lead who isn't young enough to mean the sexual subtext has to stay subtext.
239) "The Infernal Vengeance." The Magic Flute.
240) "Goblin Town." animated The Hobbit.
241) "Your Unexpected Friend." The Jungle Book's vultures.
242) "On the Prowl." Hans Brecket's whistle song from M.
243) "Welcome to the Deadmines." World of Warcraft fan song.
244) Dance number by Michael C. Hall's character in Gamer.
Another movie I came across from putting together this series that I should really watch.
245) "Big and Loud." Cats Don't Dance.
One of the later 20th century non-Disney animated efforts.
246) "I Want It Now." Verruca Salt in Willy Wonka & the Chocolate Factory.
247)  "Am I Not Pretty Enough?". Lola Stone from The Loved Ones.
248)  "A Beast Am I." From the Surtur Rising album by death metal band Amon Amarth.
So Metalocalypse is pretty on the nose, huh?
249) "The Acid Queen." Tina Turner in Tommy.
Turner's got such great energy here. I don't know anything about the movie's quality, but she makes this scene good--although it does kind of remind me of Clone High's mock rock opera. The visuals are, appropriately, pretty trippy. 
250) "Friends on the Other Side." The Princess and the Frog.
It's not a bad song, but Disney set the bar pretty damn high, from "Be Prepared" to "Poor Unfortunate Souls" to "Hellfire." For a Disney villain song, you bring the A game, or you stay home.
251) "Within You." Labyrinth. (favorite)
Maybe my favorite Labyrinth song. I love the Escher background in the video, and there's even a bit of tension as to whether she can get to her brother before one of them fall afoul of the area's twisted physics. Although what I said earlier about subtext--it's not really very sub at all, is it?
252) "Coffin Joe Samba."
I... think it's a villain song? Sometimes the language barrier gets the better of me. 
253) "Midrautus Vras." Summoning.
This is a song based on the partial language Tolkien invented for the "evil" races in Lord of the Rings.
254) "You Got Trouble." Music Man.
Clearly the inspiration for the Simpsons' monorail episode, right?
255) "Sher Khan's Lost Song." Jungle Book.
It's a deleted song that doesn't make the cut, featuring the back and forth hunting between Sher Khan and a hunter. It's an interesting take on the character, but doesn't really fit the tone of the movie, from what I recall, so I imagine that's why it got cut.
256) "Main Hoon Don." From the film Don.
Again, I've taken other people's word for it that this song from a Hindi film qualifies as a villain song--my understanding is the titular Don is a drug lord in the film.
257) "My Name is Norman Bates." 
258) "Rainbow Factory."  My Little Pony.
My understanding is that this started off as a My Little Pony fan fic story, and the song came after. Either way--creepy. 
259) "Blame Canada." The South Park Movie.
Is Canada the villain? Is South Park? Mysteries abound.
260) "Career of Evil." Blue Oyster Cult.
261) "Fifteen Birds." The Hobbit.
This clip manages make Gandalf look disturbingly murderous and all the other characters even tinier than I pictured them. 
262) "Where Has Everybody Gone." by the Pretenders. Living Daylights.(From the James Bond film.)
Ok, the villain part's a little tenuous here, I'll admit. 
263) Black Beard vs. Al Capone. Epic Rap Battles of History.
264) "Never Smile at a Crocodile." Peter Pan.
With very little rewriting, you could make a case for Peter being the villain of Peter Pan.
265) "Supper Time." Little Shop of Horrors.
266) Cutting Edge. Brave Little Toaster. 
Weird little movie. I'd like to watch it again, and see if it still holds up. If nothing else, I imagine there will be some hilariously outdated technology references. For some reason, anthropomorphizing our disposable gadgets always struck me as creepier than doing it for our animals (with the exception of fast food commercials with anthropomorphisms that apply to fastfood characters. Does the MacDonald bird lady know what happens to those birds? Is she some sort of Judas goat figure?) I'll cut it as a villain song, as they're fairly antagonistic to the main cast. 
267) "Goldeneye." from the James Bond movie.
More Tina Turner!
268) "Evil Queen Marjoly."  From the videogame Rhapsody.
My understanding is that this is from a role-playing game where the cutscenes include frequent musical numbers. I want to play this. Although even by Japanese videogame standards, that's a ridiculous outfit.
269) "Here We Go, Another Plan." Smee, from Peter Pan.
270) "I Am the Pirate King." Pirate Movie.
There's a lot of pirate songs, in general. I suppose it gets kind of dull between pillagings.
271) "God's Little Children." Tom and Jerry: the Movie.
Not as good a song as "What Do We Care" and not weirdly sexually charged like "Money"--it's the firm third place. Still, it's unusual for a film to have three villain songs starring three different villains. 
272) "The World is Not Enough." Garbage, from the James Bond film.
273) "I Put a Spell On You." Hocus Pocus. (favorite)
Chalk this one up to nostalgia glasses, but... c'mon. It's Bette Middler singing a song about putting spells on people while she is literally putting spells on people. What's not to like? 
274) "Ding Dong The Witch Is Dead." Wizard of Oz.
275) "Rake's Song." The Decemberists.
This is a dark, dark song. There's villain songs, and then there's this sort of thing.
276) "A Little Priest." Sweeney Todd.
So many Sweeney Todd songs to choose from, and I wound up using this one twice--I replaced 355, the other double-dipper, with a different Sweeny T ballad.
277) "Yzmopolis." Emperor's New School.
Song, I don't care what you're trying to tell me, the made up word "Yzmopolis" does not count as a rhyme for metropolis. 
278) "Gimme the Prize." Highlander.
279) "I'll Be Back" Monster Ballad's Terminator song.
280) "I'll Be Back." Arnee and the Terminators.
Even One Hit Wonders can make villain songs.
281) "Todd the T1000." Jonathan Coulton.
282) "Savages." Pocohontas.
The villain is prejudice. Also Ratcliffe, I guess. 
283) "Mark It Up." Repo!: The Genetic Opera.
Another musical where nearly every song is a villain song. I don't really care for the film, to be honest. The wackiness clashes with the gore. I imagine it's one to watch in theatres, or live--where you've got the reactions of the rest of the audience to build on.
284) "I Want the Good Times Back." Little Mermaid musical.
I've said this before, but there are a LOT of Ursala songs. Not that I'm complaining. 
285) "New Jack Hustler." from the New Jack City film.
286) "A Quiet Life." Dracula: the Musical. 
287) "Moonchild." Iron Maiden.
288) "TO Dance Again." A Very Potter Musical.  Voldemort and Quirrell.
289) "Les Poissons." The Little Mermaid.
I took a Cosmetics and Aesthetics course once that looked at The Little Mermaid. One of the main conclusions we came to is that, between Sebastian and Louis, Disney films used to be a lot more willing to push the "comedic" foreign accent button.
290) "New York New York." Gremlins II.
It's probably for the best I never saw Gremlins when it came out--I have a feeling it would have scared child me pretty thoroughly. But I like to think that I'd appreciate this part no matter what my age. The sheer absurdity is nice. 
291) "Professional Pirate." Muppets Treasure Island. 
For all that I've used Tim Curry as my personal punching bag in this series, he really does have a great voice for a villain song. And this is an example of how it can really work out. 
292) "Shiver My Timbers." Muppets Treasure Island. (favorite)
This song, though, is my favorite from the film. It does a great job of countering Silver's "band of brothers" narrative, and it really draws the viewer in. (Which is good, because the first act of Muppets Treasure Island is a little slow.) The totem heads singing broken English... dates it, somewhat, I'll admit.
293) "Dance or Else." Freddy's Greatest Hits. 
294) "Hardknock Life." Dr Evil in Austin Powers 2.
295) "Gold." Repo!: The Genetic Opera.
296) "Henchman." Kirby Krackle.
297) "Sweet Child." Little Mermaid Musical.
In a radical departure from norm, this villain song is not for Ursula, but her two hench-eels, Flotsam and Jetsam. 
298) "Night Surgeon." Repo!: The Genetic Opera.
This marked a turning point, of sorts, in my Repo! picks; the one theme in commenters' responses to the earlier ones where "when are you going to get to the damn Anthony Head songs?". Now. I got to them now. Not to be confused with "Night Sturgeon," the Fish-Faced Avenger. 
299) "Blowhole Power." Penguins of Madagascar. Dr Blowhole.
So for those keeping track, Neil Patrick Harris has multiple villain songs for three different villains: Dr Horrible, Music Meister, and Dr. Blowhole. Man filled a niche.
300) "A Secret of Survival in a Very Nasty World." Wind in the Willows. (favorite)
I've never read Wind in the Willows, or seen any film version. But this song regularly makes top villain song lists, and its sheer bizarre creepiness explains why. 
301) "Want You Gone." GlaDOS, Portal 2 (videogame). (favorite)
This, in fact, was the song that I meant to do as my 300th. Jonathan Coulton basically returns to the same schtick he used for the for first Portal game's song: GlaDOS is an insecure, passive-aggressive computer who's not above using gender normativity to shame her subjects ("Maybe not quite as heavy"). But even though it's the same subject area, he finds more to do with  it, and I'd say it's a better song than the original--even though the original is one of the best videogame villain songs as well. 
302) "Feeling Good About Being Bad." Mr Burns from The Simpsons.
I don't have a lot of patience for anything Simpsons-related after the 10th season or so, but I will grudgingly accept that this isn't entirely terrible. 
303) "Ignorance is Bliss." Jellyfish's song starring Bowser.
I wouldn't call this a favorite, but I do feel some strange sympathy for the lizard who's arguably the biggest, best-known villain in videogame history.
304) "The Great Mighty Poo." from the videogame Conker's Bad Fur Day.
I know some N64 owners have fond memories of this game and this fight, but... it's singing poop. I didn't think it was funny when South Park did it, I didn't think it was funny here.
305) "Master of Your Fate." Teen Titans cartoon, starring Mumbo.
Some of Teen Titans' best episodes tended towards the wackier, as this clip attests. Mumbo is not as weird as Mad Mod, but the song has appeal for me just because it's voiced by Tom Kenney, the guy who voices the Ice King on Adventure Time.
306) "Let's Talk About Me." Muppet Movie. Tex Richman.
I do like the over the top nature of this song, but Richman himself is just kind of a blank villain slate for the film. I much prefer Ricky Gervais' performance in Muppets Most Wanted--it just give him more to do.
307) Due Vendetta Protomen. (favorite)
A little background here:Another song from the Megaman rock opera. 
308) "Phantom of the Opera." Iron Maiden.
309) "Wands Out." Slytherin House Mix-tape. Adam Warrock and Mikal Khill.
This song marked a first--out of all the tweets, this was the only one that got a response from the original composer, Khill. Warrock's done a lot of villain songs; it's good work.
310) Digimon villain song. From Maximillion Pegasus.
311) "Final Boss." MC Frontalot.
312) "Freeze Machine." Care Bears Battle the Freeze Machine.
Looking back, the Care Bears are basically Veggie Tales with less overt Christian overtones. ...That might be part of the popularity, come to think of it. That and sympathetic villains. Was anyone else rooting for Shrieky and Beastly?
313) "Phony King of England." animated Robin Hood.
314) "Do the Freddy."  Freddy's Greatest Hits.
The Freddy's basically the Twist, with more of a stabbing motion.
315) "We Do Not Sow." Adam Warrock. (He's referring to the Greyjoys of Game of Thrones.)
316) "How Can You Refuse." Barbie: Princess and the Pauper. 
317) "My Name." Oliver.
318) "Mordred's Lullabye." Heather Dale.
The chorus of the song bugs me a bit--the repeated "loyalty" gets old--but it does a great job of establishing just how doomed Mordred was, a theme that comes up every now and then in the Arthur mythos.
319) "I Can't Decide."  Doctor Who.
I loved this season of Dr Who. Martha was a great companion, the plot moved forward in a way that didn't seem entirely random, and, as in this clip, it had a great villain.
320) "Magneto and Titanium Man." Paul McCartney and the Wings.
This is a weird song to exist. 
321) "I am King." Dougal and the Blue Cat.
322) "Kiss Me, Son of God." They Might Be Giants. 
323) "Not Over Yet." A Very Potter Sequel. Lucius and the Death Eaters.
I like the plot of the musical--deciding there's one last shot, Lucius and co., having lost the bad fight against Harry, pull some time traveling shenanigans to go back into the past and stop Harry from being born. Back the the Future with magic, in other words. I'd watch that. 
324) "Magneto was right." Adam Warrock.
325) "Dracula." The Muppets.
And then there was that time that Alice Cooper was on the Muppets and played Dracula. 
326) "B-Movie." Brave Little Toaster. 
Probably more villainous than the other Brave Little Toaster song.
327) "Death Death Devil Devil Evil Evil Songs." Voltaire.
328) "Like A Million."  Emperor's New Groove 2. 
Oh, Kitt. 
329) Loki's Song. 
330) "Goodbye Soon." Great Mouse Detective.
Now, a Vincent Price and Ertha Kitt villain song duet... Imagine those two singing "Evil Love." 
331) "Mina's Seduction." Dracula: The Musical.
332) "Bastard King." 
333) "Wicked Witch."
334) "Witch's Lament." From the musical Into the Woods.
335) "Meticulous Analysis of History." Pinky and the Brain.
336) "Thankless Job." Repo!: The Genetic Opera
337) "Descent of the Archangel." Kamelot.
338) "Robot Masters." The Megas.
The OTHER musical group known for basing themselves off of the Mega Man franchise. 
339) "The song of Fellagund's Battle with Sauron." Elizabeth Petrenko.
My understanding is that it's a musical version of this song from the Silmarillion. 
340) "This Day." My Little Pony: Friendship is Magic.
Technically, it's a duet between the villain and the pony she's impersonating, but it covers the "sing about evil" part well enough.
341) "Ambition." Slytherin House Mixtape. Adam Warrock and Mikal Khill.
342) "On the Rise." Dr Horrible. (favorite)
Oh, Billy. In any other context, the stalker intent on pressuring a girl to move him out of a friendzone would be the story's villain, but, well, you DO claim to be the piece's villain. 
343)  "Remember You." Ice King and Marceline, Adventure Time. (favorite)
Admittedly, this is a song that requires a fondness and appreciation for the source material; the episode is a flash-back/retcon, and the song is the culmination of that revelation. It's very amelodic and chaotic, but it still works, for me. 
344) "Please Mr Gravediggers." David Bowie.
345) "Don't Sleep." Freddy's Greatest Hits.
346) "Cover the Sun" Reference to Mr Burns, among general villainy. Zach Lost.
Now, THAT'S how you do a villain song chorus. 
347) "Glory Train" From Randy Newman's Faust.
The Satan part doesn't come in until it's approaching the three minute part. Probably my favorite thing from Randy Newman that's not soaked in Toy Story nostalgia. Also, I gotta give props to a guy that writes a heavenly oriented musical and casts himself as Lucifer. 
348) "Come Up and Try My New Parts." Amber Sweet, from a deleted song in Repo!: The Genetic Opera. 
Repo! is not known for its subtlety. That said, I always thought the role of Sweet showed a fair amount of self-awareness on Paris Hilton's part. But then again, I guess she mastered projecting a public persona before the Kardassians made it cool. 
349) "Double Trouble." Jesse, James, and Meoweth from Pokemon.
I was a little old to jump fully into the Pokemon craze, but I appreciate the cultural impact. And considering this song (or some minor variant) played virtually every episode, it'll be a big part of a generation of kids now grown up. Team Rocket blasts off... etc.
350) "Thrawn." Adam Warrock singing about a villain from the Star Wars expanded universe.
While Thrawn's current existence is somewhat up in the air, he originally appeared in a trilogy written by Timothy Zahn; the gist is that he was a member of the tattered remains of the Empire about five years after the end of Return of the Jedi who attempted to take over the fledgling New Republic; he was characterized by meticulous plans and extremely term schemes.  I know he's become kind of cliche for being TOO awesomely foresighted, but I remember rooting for him; he just TRIED so much harder than the heroes. He deserved to win. And that's the quintessential "love to hate" villain thing. 
351) "House Party at Arkham Asylum." Joker.
352) "Life After Life." Dracula: The Musical. 
Another replacement piece; originally, I had accidentally doubled up on Verruca Salt's "I Want It Now" song from Willy Wonka and the Chocolate Factory.
353)"We are Siamese."  Lady and the Tramp.
Trivia fact: Thanks to the existence of "Everybody Wants to Be a Cat," this isn't the most racist Disney song sung by cats.
354) "Rains of Castamere." The National. Game of Thrones. (favorite)
If you're a Game of Thrones fan, you already know why this one's on the list. Also, I appreciate the National more as I hear more of them. 
355) "By the Sea." Sweeney Todd. 
This was a swapper; I accidentally played the same Sweeney Todd song twice. It's just as well, as this is one of my favorite songs of the film. I like how utterly self-deluded Mrs. Lovett is about the nature of her beloved; she's like a working class Victorian Harley Quinn. 
356) "Mine, Mine, Mine." Pocahontas. 
This time, the villain is definitely Ratcliffe.
357) "Jingle Bells." The Joker, from Batman: The Animated Series.
If Arkham Asylum security guards are really so terrible that they can't tell the difference between a tree and a rocket, that would explain a lot. 
358) "Pain and Suffering." Iggy Pop, from Rock 'n' Rule.
359) "Kill the Wabbit." Elmer Fudd.
360) "Brand New Day." Dr Horrible's Sing-A-Long Blog.
361) "Mother Knows Best." Tangled. 
It's a great villain song in terms of establishing the relationship between the villain and the protagonist, and the sheer sliminess of the villain. But not a great song.
362) "Kingslayer." Adam Warrock, Referring to Jaime Lannister of Game of Thrones.
363) "Sweet Transvestite." Dr Franken Furter, Rocky Horror Picture Show.
Might as well start wrapping things up with one last Tim Curry song, in probably his best known musical role.
364) "Sympathy for the Devil." Rolling Stones.
365) "Be Prepared." Lion King.
Finishing with the quintessential villain song. With a video from, I don't know, some guy. (I figured I could spend hours perfecting it, and still be faced with the horribleness of my voice, or I could go for as off-the-cuff, one-take as possible. Guess which one I went for?)

And that's all. But wait, that's not all! I found over five hundred songs in all, but decided that I wore out everyone's patience enough with a year's worth. So here are all the songs that I didn't find room for, didn't find villainy enough, or just didn't use, in no particular order.

"A Dead Body." Wensday 13.
"Evil Like Me." My Little Pony fan song.
"Brannigan's Law." Brannigan from Futurama, by Adam Warrock.
"Xorn." Complicated X-Men villain, by Adam Warrock.
"Gideon Graves." Scott Pilgrim Evil Ex-Boyfriend. Adam Warrock.
"The Decline of EnglishMurder." Alan Moore.
"Friends of the Working Mouse." American Tail: Treasure of Manhattan Island.
"Get in My Mouth." Aragog and the Spiders. A Very Potter Senior Year. (From the Harry Potter Musical series)
"Baba Yaga." Bartok the Magnificent.
"I've Written a Letter to Daddy." Baby Jane Hudson.
"Back and Forth." Doctor Steel.
"Bad Guys." Bugsy Malone: The Musical.
"Ho Ho Ho THe Joker's Wild." Batman Musical Stories.
"The Penguin." Batman Musical Stories.
"The Joker Gets Trumped." Batman Musical Stories.
"Do What I Want to Do." Bayou Boogie.
"Love is a Magical Mystery." Bayou Boogie.
"Bizzaro World/ Mr. Mxyzptlk." Ookla the Mok.
"Iron Man." Black Sabbath.
"Damned for all time / Blood Money." Jesus Christ: Superstar.
"Brains." Voltaire.
"My Little School." Charlotte Rae in The Worst Witch.
"Chu-Chi Face." Chitty Chitty Bang Bang.
"Those were the good old days." Damn Yankees.
"Pain of Salvation." Dead Pecuniaie.
"Police Truck." Dead Kennedys.
"The Queen's Rebuke." Decemberists.
Mojo Jojo's "Devo." from Powerpuff Girls.
"Different as can be." Voldemort and Quirrell. A Very Potter Musical.
"No Return." Phantom of the Opera.
"Down Once More." Phantom of the Opera.
"Freeze." Dr Flurry in League of Incredible Vegetables.
"There's Always a Tomorrow." Dracula The Musical.
"The Longer I Live." Dracula the Musical.
"Home." Dream Theater.
"Evil Woman." Xanadu.
"Faust." Phantom of the Paradise.
"Fiend in Wein." Inferno Friendship Society.
"Evil Mania." Freddy the Frog.
"Fi Fi Fo Fum." Giant in Mickey and the Beanstalk.
"In the Midnight Hour." Freddy's Greatest Hits.
"Obsession." Freddy's Greatest Hits.
"Speak Softly, Love." From The Godfather.
"Party." American Astronaut.
 "The Spanish Inquisition." History of the World.
"Hit Somebody." Warren Zevon.
"We're Pixies." Fairly Odd Parents
"If I'm Going to Eat Somebody." Ferngully.
"Disturbed." Inside Fire.
"Last Midnight." Into the Woods.
"Our Little World." Into the Woods.
"Stay With Me." Into the Woods.
"Alive." Jeckyll and Hyde.
"Kick it up a notch." Pincer.
"Super Villain." Kid Radio.
"WITCH's Song." Kin No Tori.
"Temptation Song." LarrBoy and the Bad Apple.
"Iced Earth." Last Laugh's Malebogia. (The whole album, really.)
"Madame Guillotine." Scarlet Pimpernel.
"Queen of the Night." Magic Flute.
"Un Mavais Dieu." Manau.
Science Bad." Adam Warrock on the comic book The Manhattan Projects.
"March of Mephisto." Kamelot.
"Me." Beauty and the Beast musical.
"Little Sister." Miracle of Sound, on Bioshock.
"Nothing Can." My Little Pony Movie.
Freddy Krueger's lullaby. Nightmare on Elm Street.
"No Bad News." The Wiz.
"No One Knows My Plan." The Wiz.
"Nothing is Free." Alice Cooper.
"Panzerlied." Battle of the Bulge.
"When I Held Your Brain." Mystery Science Theatre 3000
"Reviewing the Situation." Oliver.
Symphony X's Paradise Lost Album
"He's Dr Blowhole." Penguin Who Loved Me.
"Point of No Return." Phantom of the Opera.
"Hell of It." Phantom of the Paradise.
"Somebody Super Like You." Phantom of the Paradise.
"Wheatley's Song." Portal 2, song by Miracle of Sound.
"Toadies." Possum Kingdom.
"Supervillain." Powerman 5000.
"If I Ruled the World." Proud Family Movie.
"Things You See in a Graveyard." Repo!: The Genetic Opera.
"We Started This Opera Shit." Repo!: The Genetic Opera.
"Robot Hell." Robot Devil from Futurama.
"We Hate the Sun." Rock-A-Doodle.
"Running Gun Blues." David Bowie.
"No More Toymakers." Santa Claus is Coming to Town.
"Skeletons on Parade." Ludo.
"Khajit Like to Sneak." Miracle of Sound, taking from the Elder Scrolls videogame series.
"Snake in the Grass." Little Prince.
"Supervillain Song." SpongeBob SquarePants: The Musical.
"Staligrad." Sabaton.
"Freddy Krueger." Stormtroopers of Death.
"Mad Scientist." Suicide Booth.
"Pretty Women." Sweeney Todd.
"Johanna (reprise)." Sweeney Todd.
"Don't Mess With Me." Temposhark.
"The Bunny Song." Rack, Shack, and Benny.
"Triumph." Rock 'n' Rule.
"Stutter." Umbridge, in A Very Potter Sequel.
"Forever Young." The vampire women in Dracula: The Musical.
"Chainsaw Charlie." WASP.
"All-American Massacre." Wensday 13.
"No Good Deed." Wicked.
"Popular."  Wicked.
"You Give a Little Love." Bugsy Malone.
"Mad Scientist." Zanies.
Drakken rap. Kim Possible.
Darth Vader vs Adolf Hitler 1. Epic Rap Battles of History.
Rasputin vs. Stalin. Epic Rap Battles of History.
"Another Pyramid." Aida.
"Blodsvept." Fintroll.
"Springtime for Hitler." The Producers.
"Der Fuerer's Face." Donald Duck cartoon.
"Villain Song." Kirby Krackle.
"Every Little Piece." Pete's Dragon.

So many songs. So much villainy. A year well spent, no doubt.

Later Days.