Credit: Disney

Once Upon a Time's season 4 finale was all about villains trying to finally achieve their happy endings. Specifically, we're talking Disney villains — a gang of throne-usurpers and puppy-murderers who are generally a lot more sympathetic on Once than they were in their original incarnations.

Then again, who ever said we wanted our Disney villains to be sympathetic? In order to earn a spot in the wicked pantheon, all a baddie really needs is a sharp chin, a killer smirk, a master plan… and, ideally, a big, bold production number in which they declare their evil intentions via song.

Some of the most memorable Disney villains ever, including Snow White's Evil Queen and Sleeping Beauty's Maleficent, don't get villain songs. Plenty of others do, though — 20, by my count, as of May 2015. So, without further ado, here's a completely scientific, totally objective* ranking of them. Note: This list only covers films released by Walt Disney Animation Studios (which means, alas, that there's no Oogie Boogie song), and I also decided to include both songs sung by villains and songs sung by other characters about villains, mainly because leaving out the latter would mean disqualifying two of the best villain songs ever. Also: There's no "Love Is an Open Door," because c'mon.

*Science and objectiveness not guaranteed

20. The Siamese cat song, Lady and the Tramp

NOOOOOOO. A racist, embarrassing mess that's straight-up hard to watch in the 21st century. You might think it couldn't get worse than the original… but you're wrong, my friend.

19. "Hellfire," The Hunchback of Notre Dame

Ahh, a lust-crazed magistrate crooning about how he yearns to touch Animated Demi Moore's boobs — just what I look for in my kiddie entertainment! "Think of the children" aside, this one's just too derivative to score major points; it sounds like a Javert ballad that got left on the cutting-room floor, which is really saying something, considering the Javert songs that actually made it into Les Mis.

18. "The Elegant Captain Hook," Peter Pan

Herewith begins a stretch of tunes that do count as villain songs, but only barely; they're all reprises of other, better songs. The least distinguished of them is this reworking of "A Pirate's Life," proof positive that the Mary Martin Peter Pan has better music than the Disney version. ("Elegant" hardly holds a candle to "Captain Hook's Waltz.")

17. "Who's Been Painting My Roses Red," Alice in Wonderland

Again: There's not much there there, even if a rose is a rose is a rose.

16. "Prince Ali (Reprise)," Aladdin

What a shame that one of the Disney renaissance's most captivating figures doesn't get a full-length villain song to call his own. (Not that Howard Ashman, Alan Menken, and Tim Rice didn't try—all told, they wrote four real Jafar songs, none of which made it into the final movie.) At least voice actor Jonathan Freeman finally got his chance to shine in Aladdin on Broadway.

15. "Trust in Me," The Jungle Book

You know what's a wonderful song? "I Wanna Be Like You," sung by the charismatic (and geographically problematic) orangutan King Louie. It seems off to label that one a villain song, though, since Louie isn't the movie's primary antagonist — that'd be evil tiger Shere Khan. But Shere Khan doesn't have a song… so we'll split the difference by considering evil python Kaa's hypnotic anthem. Put it this way: There's a reason he uses it to put people to sleep.

14. "Yodel-Adle-Eedle-Idle-O," Home on the Range

Remember Home on the Range? Of course you don't! It's the 2004 musical that always ruins your score on this Sporcle quiz, and a bomb that nearly had the dishonor of being Disney's last traditionally animated movie. No, this song isn't a masterpiece—though the yodeling's kinda fun, and Randy Quaid sounds surprisingly good as bad guy Alameda Slim, a dastardly cattle thief. (The talking cows he tangles with, by the way, are voiced by Roseanne Barr, Jennifer Tilly…and Judi DenchWhat is this movie?!)

13. "World's Greatest Criminal Mind," The Great Mouse Detective

Meh movie, meh song. Rattigan may not be the world's worst criminal mind, but he's certainly not the greatest.

12. "Mad Madam Mim," The Sword in the Stone

Nobody ever remembers poor Madam Mim. As the name implies, she's more gleeful agent of chaos than capital-E Evil — and her signature song is an enjoyably frenetic Sherman Bros. tune, fun if not particularly memorable.

11. "Mine, Mine, Mine," Pocahontas

Catchy enough, though that's probably just because it sounds like a 1776 B-side. (Psst, Governor Ratcliffe: You are no John Dickinson.)

10. "Headless Horseman," The Adventures of Ichabod and Mr. Toad

Hey, did you know that Bing Crosby voices, like, everybody in Disney's take on "The Legend of Sleepy Hollow" — including arrogant proto-Gaston Brom Bones, who croons this delightful, swingin' bit of musical exposition? It's also doubly villainous, since Brom not only sings about the Horseman, but (presumably) impersonates him in order to run Ichabod Crane out of town.

9. "Mother Knows Best," Tangled 

Why wasn't Tangled as mega-successful as Frozen? Who knows—but maybe it's because the Rapunzel movie doesn't have any songs nearly as ear-wormy as "Let It Go" or "Do You Want to Build a Snowman?" (Well, except "When Will My Life Begin," maybe.) Mother Gothel has admirable swagger in her big number, but that can't elevate it higher than the middle of the pack.

8. "The Phony King of England," Robin Hood

A good, old-fashioned, fife-heavy Medieval hoedown. "Too late to be known as John the First, he's sure to be known as John the Worst." Sick burn, Little John.

7. "Heffalumps and Woozles," The Many Adventures of Winnie the Pooh

Yes, it owes more than a little to "Pink Elephants on Parade" (does that count as a villain song? Eh, I'm gonna say no), and yes, the instrumental break goes on way too long — but damned if it's not both incredibly catchy and the most legitimately terrifying song on this list. (Not to mention a fascinating example of what happens when trippy late '60s psychedelia worms its way into children's entertainment.) Size, SIZE, size, SIZE! My apologies for bringing back your childhood nightmares.

6. "Hi-Diddle-Dee-Dee," Pinocchio

You forgot this one existed, but now it's stuck in your head forever. Sorry!

5. "Friends on the Other Side," The Princess and the Frog

Man, why wasn't all of The Princess and the Frog as awesome as this sequence? I could listen to Dr. Facilier's smooth bass all the livelong (die-long?) day.

4. "Cruella de Vil," One Hundred and One Dalmatians

Real talk: There is the finest hair separating each of the top four entries on this list. Each one has a reasonable claim for the number one spot; I'd understand placing them in any order. Here, though, is why I'm raking them the way I do. First: "Cruella" is unspeakably great, not least because of Roger's ultra-petulant one-man-band — but there's just not enough song there. I want more verses, damnit!

3. "Be Prepared," The Lion King

It's more than just a spine-tingling production number — it's also a valuable education in both vocabulary ("retention," "sordid," "quid pro quo," "addressee") and Nazi iconography.

2. "Poor Unfortunate Souls," The Little Mermaid

Unlike "Cruella," Ursula's big number is a masterpiece of excess — tongue-twisting verses, bitchy eel-focused asides, lengthy dialogue interlude, key change, one hell of a crescendo. It's brash, bold, and almost, almost unbeatable.

1. "Gaston," Beauty and the Beast

Is it a searingly clever critique of traditional hegemonic masculinity? You bet your ass it is! But more importantly, this rousing drinking song is straight-up fun from start to finish, an admirably economic anthem that doesn't waste a single word or note. It easily paints a full picture of Gaston and everything he stands for, doing more character work in three minutes than some movies do in 90 — but you'll be too busy singing along to even notice how smart this song is. And every last inch of it's covered in HAIR!

Episode Recaps

Beauty and the Beast (TV Series)
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