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The 20 Funniest Comedy Musicians of All Time

Need a good laugh but tired of your typical stand-up comedy specials where the comedians just talk? Talking is boring! Overrated! Stupid, even! You need musical comedy instead. And boy, are there so many underappreciated comedy musicians out there.

Musical comedy has been around since like...people wore togas during the ancient times. But it didn't become modernized until around the 20th century when music became easier to record. Comedy music had a bit of a golden age around the 60s and 70s (thanks in part to radio broadcasters like Dr. Demento), and exploded once the 80s, 90s, and early 2000s hit. While it's still a very niche subgenre of music, it's definitely growing. So long as the internet and its memes are around, comedy music will always be there.

We're about to present you with our 20 favorite comedy artists EVER. But we should mention we do have some boundaries for this list. We're not including fictional comedy bands (like Spinal Tap) or theatre troupes (such as Starkid), or WEB SHOWS rather than actual musicians (for example: Epic Rap Battles of History or Don't Hug Me I'm Scared). Instead, we're focusing on solo comedy artists and bands who have done tours, created albums, and made shows with their own musical name brand. Don't worry: they're all dorky superstars in their own special way.

We're hope you're ready to laugh until your belly hurts. Here are the 20 funniest comedy musicians of all time!

1. "Weird Al" Yankovic

Of course, the Prince of Parodies has to be first on our list. "Weird Al" ruled the 80s with his accordion skills and special flavor of musical comedy, then successfully maintained his career at the start of the digital age by putting out wacky music videos on YouTube. Our favorites from him include "Eat It", "Like a Surgeon", "Amish Paradise", "White & Nerdy", "Smells Like Nirvana" and "Another One Rides the Bus". In the 2020's, his career is still going strong. He recently put out a new movie - Weird: The Al Yankovic Story - that's (very loosely) based around his life.


2. Bo Burnham

Whether he's doing live shows or foraying into film, Bo Burnham has a way of making everyone laugh and think deeply about race, gender, sex, religion and existensialism at the same time. Burnham started out his career in 2006 with silly keyboard videos that went viral. He later signed a deal with Comedy Central Records and at seventeen became the youngest person to film a comedy special for the channel. After doing various successful live comedy shows, Burnham directed his first feature film Eighth Grade. Amidst the pandemic, he then returned to his roots with his magnum opus Netflix special Inside. Funny, dark, and a look inside Burnham's mental health, he gained acclaim with songs like "That Funny Feeling", "Welcome to the Internet", "Content", and "Bezos I".


3. Garfunkel & Oates

We consider these ladies the OG queens of comedy music. Riki Lindhome and Kate Micucci make up Garfunkel & Oates, and their vibrato-less brand of folk music is anything BUT folksy. It's actually pretty raunchy, but hilariously honest. Whether they're singing about God's loophole to virginity or your friend Steve, Garfunkel & Oates don't hold anything back. More people need to watch their self-titled 2014 IFC show.


4. The Lonely Island

These guys helped bring about a revival of SNL thanks to how freaking funny they were. The Lonely Island is comprised of Andy Samberg, Akiva Schaffer and Jorma Taccone. The historic sketch show would feature the trio within their pre-filmed sketches, which included songs like "Threw It On the Ground", "I'm On a Boat", "Like a Boss" and the Michael Bolton team-up "Jack Sparrow". Their bold, club-ready absurdist bangers span across four studio albums, and they even earned a Grammy nomination for Best Comedy Album with Turtleneck & Chain.


5. Tom Lehrer

He may be an old-school 50s and 60s crooner, but his songs are hysterical decades later. Tom Lehrer would play piano ballads about twisted things: like poisoning pigeons in the park or pollution in American cities. Deemed problematic, radio stations refused to broadcast his music - which only resulted in him gaining a cult following. Unsurprisingly, Lehrer’s songs got more political as the 60s rolled around, tackling signicant issues like racism and nuclear warfare. It wouldn't be an understatement to say Lehrer's piano tunes walked so several other artists on this list could run.


6. Tenacious D

By now, we know that whatever musical endeavor Jack Black puts out is bound to be hilarious. Back in the 90s, him and fellow Actors' Gang member Kyle Gass created the comedic rock duo Tenacious D. They had a ball-busting self-titled debut album that dropped in 2001. 2006 was a big year for the men, as they released both a hysterical album and movie called The Pick of Destiny. They continue to release records, EPs, and singles, but we'll never forget the gusto they put into their earlier work. Especially in their hit song "Tribute". We could listen to those "Goo-guh fli-goo gee-goo's" for hours.


7. Flight of the Conchords

Before Jemaine Clement was hanging with a bunch of vampires in What We Do In the Shadows, him and Bret McKenzie were putting out funny songs as part of their duo, Flight of the Conchords. This pair of New Zealanders had their own TV show from 2007 to 2009, and they still make music when their schedules are free. They originally formed in 1998 when they were college roommates. By 2004, their more polished act allowed them to improvise on their own BBC2 radio series. This ultimately paved the way for their American mockumentary experience, Flight of the Conchords: A Texan Odyssey. We recommend starting with their songs "If You're Into It" and "The Most Beautiful Girl (In the Room)" if you want to know what they're about.


8. Tim Minchin

If we didn't have Tim Minchin to guide us, we wouldn't know that only a ginger can call another ginger ginger! Minchin is a British-born Australian comedian. And yes, he is ginger. Minchin never actually attended a comedy show before the start of his career. But you'd never know that, because he has such a crowd-pleasing stage presence. Standouts in his socially-aware discography include the singles "Prejudice", "Confessions" and "Inflatable You". His satirical songs span across two studio albums and six live albums. He's also acted as the composer and lyricist for the musical versions of Matilda and Groundhog Day.


9. Steve Martin

He's more than just a screen actor: Steve Martin makes a comedic tune every now and then. His most famous is probably "King Tut", which famously aired on SNL in 1978. But he's got plenty of other goofy hits, like "Atheists Don't Have No Songs" and the topsy-turvy "Late for School". Armed with his trademark banjo, Martin's humorous songs are all quirky, happy-go-lucky, and narratively rich.


10. Stephen Lynch

Whether he's singing about his ugly baby or Jesus' brother Craig, Stephen Lynch has a way of getting our undivided attention. This Michigander musician has songs that typically start off calm and innocent, but then zing you with an out-of-nowhere twist. Stephen Lynch has a big enough funny bone that he could thrive as a stand-up comic if he wanted to, but the humble guitar coupled with absurdist lyrics just makes his act ten times better.


11. Steel Panther

Don't be fooled: these heavy metal studs are nothing like the 80s bands your dad listens to. Steel Panther formed at the turn of the millennium in Los Angeles. They've done songs, live shows and videos parodying the stereotypical glam metal genre and rock n' roll lifestyle of the 1980s. They're like Spinal Tap, but not fictional. With racy songs such as "Gloryhole" "Death to All But Metal" and "Community Property", this NSFW band may offend your parents, but they WILL make you cry laughing!


12. Rachel Bloom

You may know her from the CW show Crazy Ex-Girlfriend, but Rachel Bloom actually got her first dose of fame when she released her sexually explicit song about science fiction writer Ray Bradbury in 2010. We love her amusing takes on the female experience, like "Heavy Boobs", "Let's Generalize About Men", and "The Sexy Getting Ready Song". We can't wait to watch her upcoming Off-Broadway musical, "Death"!


13. Ninja Sex Party

Composed of Danny Sexbang and Ninja Brian, Ninja Sex Party is a comedy synth-pop duo that has dominated the internet - particularly YouTube - since 2009. As their name would suggest, the two goofballs offer up musical advice about how to take control of your sex life. But they also have educational tunes about how to look...cool? Or at least their version of cool. ("I Own a Car" and "Cool Patrol" come to mind.) Ninja Sex Party has recorded five albums of original material, three cover albums and one re-recording album. Ever since their LP Under the Covers, they've been backed by the band TWRP. For three albums, they've collaborated with animator and internet personality Arin "Egoraptor" Hanson to create the video game themed side project Starbomb.


14. Lil Dicky

Either he's a rapper who takes himself too seriously or a genius musical comedian. We still don't totally know for sure. But if there's one thing we do know, it's that Lil Dicky's hip-hop songs make us crack up. Lil Dicky got his start on YouTube when the music video for his song, “Ex-Boyfriend” went viral in 2013. After two years and a Kickstarter campaign, he released his debut album, Professional Rapper. It topped comedy charts and would eventually lead him to creating his own TV show, Dave. Oh, and he's had the chance to collaborate with several acclaimed artists - like Snoop Dogg and Brendon Urie.


15. Ray Stevens

We're surprised not too many musical comedians go the Ray Stevens route and do silly country songs. But hey, maybe it's because Ray Stevens already does it so well. With a career spanning over sixty years, Stevens has taken on producing, publishing and songwriting roles for his absurdist brand of country novelty tunes. Whether he's singing about a Mississippi squirrel in the church or a streaker at the grocery store, Stevens is able to perfectly blend the silliness of hillbilly music with his satire. And the critics dig it, too: Stevens has won two Grammys and has received twelve nominations for his work!


16. Da Vinci's Notebook

If you need songs that help you give gratitude to your enormous penis or Irish drinking lifestyle, boy do we have the group for you. Da Vinci's Notebook was a comedic a cappella singing group around during the 90s and early 2000s. They were former Artists-in-Residence at the John F. Kennedy Center for the Performing Arts, and performed specials on Comedy Central and PBS. They also spent time as the "house band" on Washington radio's WBIG-FM and were regular guests on the nationally syndicated Bob and Tom radio show. If you're a comedy music fan, do yourself a favor and listen to the entirety of Brontosaurus.


17. Reggie Watts

Reggie Watts is that kind of comedian where, even if he's doing something totally incomprehensible, it's still hilarious. A master at musical improv, Watts has built his entire career of off beatboxing, a keyboard, and a looping machine. We can't describe his improvised songs: you just have to watch his performances for yourself. His secret formula of funny eventually drew the attention of James Corden, and he served as the bandleader on The Late Late Show for its entire run from 2015 to 2023.


18. Marc Rebillet

Similar to Reggie Watts, internet comedy newcomer Marc Rebillet is also talented in musical improv. His short songs are typically either R&B funk tunes or dancy electronic bangers - but they're always laced with sensual and/or aggressive vocals and scantily-clad looks. (He's usually either in a robe or just his boxers.) His most popular tune at the moment is his under-a-minute track "YOUR NEW MORNING ALARM": a rave-worthy jam where Rebillet parties around his crib and screams into the microphone, encouraging listeners to "get the f--- out of bed b----, go!" Ironically, many fans have already set it as their morning alarm.


19. Allan Sherman

Yup, we're including the "Hello Muddah, Hello Fadduh" guy on our list. Allan Sherman's most popular comedy tune chronicles a little boy having a torturous experience at summer camp. But he also put out other silly hits during the 1960s, such as "My Son, the Folk Singer" and "Harvey and Sheila". Sherman started his career out as a game show writer and producer, but through his songs, would eventually top the charts in the early 60s with a trio of comedy albums. He even bagged a Grammy nomination for Album of the Year for his debut record! Sherman's songs experienced heavy airplay once Dr. Demento graced the radiowaves in the 70s.


20. Spike Jones

Last but not least, the man many consider as the godfather of modern comedy music. Maybe Spike Jones didn't write super raunchy tracks with belly-busting lyrics, but he did make many people laugh in the 1930s and 40s with his funny noises. With his band, the City Slickers, Jones spoofed popular songs of his era by injecting outlandish sound effects like gunshots, whistles, and other bizarre musical instruments, elevating their music above mere comical lyrics. You may think that's rudimentary, but trust us: the hilarity of it all still holds up decades later. You've got to watch his performances for yourself to understand how entertaining it is!


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Article Image: "Weird Al" Yankovic in Jedi robes during a 2004 concert, close-up of Reggie Watts belting into a microphone, Bo Burnham performs at a 2009 show. (BstarXO Chester L. Roberts [CC BY-SA 3.0], PopTech [CC BY-SA 2.0], and Jeffrey Mann [CC BY-SA 3.0] via Wikimedia Commons.)

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About Kathryn Milewski

  • New Jersey