Top 10 Funniest Songs By Comedians Ever

Monty Python
This song has been recorded, performed and released a number of different ways, but Monty Python fans can likely name one particular place where it was done the best. Yes, we’re talking about "Always Look on the Bright Side of Life," and its use in the comedy troupe's legendary "Life of Brian." The song pokes fun at the "Keep Calm and Carry On" reputation of British stoicism, even in the face of the worst imaginable odds. That’s why it's so funny to hear it in "Monty Python's The Life of Brian” when the titular character is meeting a grim fate. It's honestly a movie moment that we never get tired of watching over and over again.

Flight of the Conchords
Musical comedy can be a difficult genre to stand out in. But New Zealand duo Flight of the Conchords manages to do so thanks to a uniquely whimsical musical style. While the group has a variety of funny songs, "Albi the Racist Dragon" might be the most hilarious tune they have from their self-titled sitcom. Perhaps it’s because of the song’s almost pastoral English folk style. Bret McKenzie plays guitar and sings backup to Jemaine Clement's short and strange tale about a hateful and exiled dragon. They also make lyrics about an outcast boy who's badly harmed by Albi's flaming breath wickedly funny. A heartfelt exchange, and a couple of dragon tears that turn into jelly beans later, and everything is fine somehow: [1: And he wasn't racist anymore"]

Julie Brown
If you're a music fan of a certain age, then you likely have fond memories of the Dr. Demento radio show, a syndicated series that featured weird and wacky novelty songs. That show assisted in getting a darkly comedic gem by Julie Brown lots of attention, and we're glad it did. "The Homecoming Queen's Got a Gun" is a wicked take on those depressing golden oldies like "Leader of the Pack," that always seemed to end in tragedy. Brown's version is steeped in 1980s Valley Girl culture and is hyper violent. The titular Homecoming Queen goes on a rampage until she meets a violent end. Her final words about "doing it for Johnny" also appear to parody a famous teen delinquent tale, "The Outsiders."

The Lonely Island feat. T-Pain
It was extremely difficult for us to narrow down a favorite jam by The Lonely Island for this list. Ultimately, however, we had to go with "I'm On a Boat." The premise is so silly, yet so simply effective: it’s all about that joyous feeling of being out on the open sea. Poseidon, God of the Sea gets an excellent name drop. Nautical-themed clothing is also shown some serious love and T-Pain's famous auto tune does a lot of heavy lifting. The approach is also...we're gonna say "needlessly aggressive?" But that's also part of the charm: it's an aggro tune about heading out on a boat, having a great time, and yelling it all out to the world.

Bo Burnham
Bo Burnham has achieved a lot of success at just 30 years of age. And you know what? It's all well deserved. Burnham's unique style of musical comedy can be both insanely dark and insanely funny, with "Art is Dead" being great proof of that sentiment. The song is a savage parody of the creative process. It’s also an admission to his audience that performers can be emotionally stunted and hungry for attention. He sings comparisons to being at a children's birthday party to the tune of an upbeat piano number, but the implications are dark and surprisingly revelatory. Bo Burnham is simply brilliant here.

Garfunkel and Oates
Comedic folk duo Garfunkel Oates took a hilariously unexpected shot at expecting mothers with this tune. The humor of "Pregnant Women Are Smug" hits on multiple levels. The lyrics have the duo react to common conversations with expecting mothers with hilariously angry and over-the-top responses. Also, the actual style of the song is performed with the sort of ethereal femininity that parodies “chick rock" genre stereotypes. Finally, there's the accompanying music video, which actually ends with Garfunkel and Oates emerging through a prop womb into the world! You gotta see and hear this hilarious song to believe it’s real.

Tenacious D
There's a cornucopia of musical comedy heavy hitters on Tenacious D's eponymous debut album, but "Tribute" just might be the best. Maybe it's the song's note perfect take on overtly ambitious, some might say "overblown" heavy metal epics of the late seventies and eighties. Maybe it's the awesome music video that features the “Foo Fighters'’ Dave Grohl guest starring as a demon? Or, perhaps it's the fact that Jack Black and Kyle Gass actually play really well together? We're gonna go with "all of the above," because if there's any song that perfectly distills the comedic essence of Tenacious D down into a single word, it's "Tribute."

Steve Martin and the Toot Uncommons
There's no other way to say it: the success of Steve Martin's hit song "King Tut" was just lightning in a bottle. Here, it's important to note that when this song was released in 1978, the actual exhumed artifacts from King Tut's tomb had been making the museum rounds across the United States. With Ancient Egypt firmly in the public eye, comic legend Steve Martin gathered up members of the “Nitty Gritty Dirt Band” to form a group called the "Toot Uncommons" and a legend was born. The song was released on Martin's iconic comedy album "A Wild and Crazy Guy.” But it was its wild performance on "Saturday Night Live" that made "King Tut" a timeless piece of comedy history.

Adam Sandler
Speaking of "Saturday Night Live," many comedians who've passed through its hallowed halls have tried to break out on a solo career of their own...with varying degrees of success. Adam Sandler became one of the most successful SNL alums out there with the help of a few viral hits. "Lunch Lady Land" was an early smash from his tenure on the show, but it's "The Hanukkah Song" that just might be Sandler's lasting musical comedy legacy. The song is played to this day on radio during the holidays. That’s not bad for a tune that largely rattles off the names of Jewish celebrities and artists. From David Lee Roth lighting the menorah to the conversion of Hall of Famer Rod Carew, we love hearing this song every year.


Before we name our number one pick, here are some honorable mentions!

"Rappin' Rodney" (1983), Rodney Dangerfield
We Give This One TONS of Respect

"Take Off" (1982), Rick Moranis & Dave Thomas
With Guest Geddy Lee!

"Prejudice" (2009), Tim Minchin
Toeing Some Controversial Lines


"Dating the Pope" (2008), Judy Tenuta
Once You Hear Judy's Voice, You Never Forget It


"Ouch!" (1978), The Rutles
This Beatles Parody Never Gets Old

Denis Leary
It isn't easy for a song with this much vulgar language and bad behavior to survive on the radio, but believe it or not, Denis Leary's "Asshole" continues to thrive to this day! It's a near perfect example of the comedian's fiery onstage persona, especially during the time of his "No Cure for Cancer" album. Although Leary faced industry accusations that parts of his act and the idea for "Asshole" were taken from other comics, fans didn't seem to care and the song actually saw success. While Leary's rants about tossing out Styrofoam burger containers out the window didn’t exactly age well, the song is an overblown comedic tune that’s still beloved today.