The 21 best funny songs of all time

I’ve yet to find a first-time listener who isn’t confused and amused by Liz Phair’s angsty feminist anthem. I know every single lyric and love to belt it out whenever it comes on the (satellite) radio, eliciting others (usually my husband) to cringe and laugh. The monotone singing, repetitive cursing and head-turning lyrics? You try keeping a straight face while listening.

This is what Meadow from The Sopranos would sing if she had a theme song. Try breaking it off with a mob daughter? She’ll have your legs broken with a smile. The best part is that these dark lyrics are in the style of a ’60s/Doo-Wop song.

Like a lot of songs by the Bonzo Dog Doo-Dah band, ‘The Intro & The Outro’ isn’t in-your-face funny. It’s quietly funny. Funny like if you tune in for a minute and listen to the lyrics, you might chuckle to yourself as you make a cup of coffee. The song is a very, very long introduction to the weirdest band in the world, featuring everyone from Eric Clapton on ukelele to the Incredible Shrinking Man on euphonium. 

Bo Burnham’s hit Netflix special Inside is a deep dive into the manic, lonely and wholly universal experiences of isolation during quarantine, but the musical powerhouse's darkest and funniest moment comes with the chaotic ‘Welcome to the ‘internet.’ Racing between eerie, jaunty and breakneck, Burnham's carnival-barker delivery gives a bizarre tour of everything on the internet, from activism to Harry Potter erotica, racism, murder and everything in between. It's uncomfortable laughter, sure, but hey, that’s the horror of having ‘everything and anything all of the time’... except other people. 

Doja Cat is a multi-hyphenate rapper/singer/Grammy nominee/sex symbol/influencer and one of the most popular artists in the world. She is also a cow. At least that’s what her first brush with fame would have you believe: It’s a self-released rap song featuring a video in which Doja dances in front of a green screen chanting ‘bitch I’m a cow’ in between silly-as-hell verses. It’s so dumb it’s funny, but the real joke’s on us: That signature throwback porno-funk beat is going to get stuck in your head, proving that even when she’s playing around, Doja is the real deal.

Admittedly, we could double the size of this list with just Lonely Island songs. But with respect to ‘Dick in a Box’ and ‘Jack Sparrow,’ if we're limiting things to just one, we're going with the Grammy-nomintated summer banger. Admit it – you sing this song every time you’re on a boat. The guys and T-Pain made this SNL Digital Short a ridiculous, infectious hit in 2009, and we’re still looking for any opportunity to get down with Auto-Tune on a watercraft.

Bret McKenzie and Jemaine Clement snuck a lot of sweetness into their guitar-based digi-bongo acapella-rap-funk-comedy folk repertoire, but this is the duo at their most charmingly self-effacing. Floating on top of a cloud of pretty guitars, this Flight of the Conchords number has instrumentation worthy of a good gig rather than a good giggle and a downright brutal sense of self-depreciation as all of Clement's exes assemble to point out his shortcomings. 

On its own, this whistle-swept vaudevillian number feels like a jaunty, goofy number from the Flying Circus crew. In the context of Life of Brian – where it’s played over a mass crucifixion – lines like ‘life’s a piece of shit, when you look at it’ followed by the titular refrain are downright diabolical in their hilarity.

We could put together a whole list of the best Weird Al songs. How can you pick just one amongst hilarious tracks like ‘Fat,’ ‘Eat It,’ ‘Amish Paradise,’ ‘Like a Surgeon,’ ‘Smells Like Nirvana’?. ‘White & Nerdy’ is one of the funniest though, as Weird Al takes on Chamillionaire, rapping about comic books, riding a Segway, wearing braces and owning a fanny pack. The song is Al’s biggest hit, and also helped ensure the world's greatest parody songwriter would survive to make a new generation chuckle. 

This one ain’t about scoring a really ace mark, but is about going from your 20s into (shudder) your 30s. It's a killer duet to capture this inevitable rite-of-passage: 50 percent optimism, 50 percent screaming frustration and 100 percent ukulele-flecked catchiness.