12 Comedy Acts Who Split Sides Through Song

Most comedians will admit they’d rather be rock stars. Rock stars can do sexy things like write songs and sing them for their girlfriends. What’s a comedian supposed to do? “Hey sweetie,  I spilled coffee on my crotch this morning and I wrote you this joke…”  Romantic “what’s the deal with airline food” serenades under the window sill?  There is no waving of Zippos/cell phones or crowd surfing at comedy shows.  On the other hand I  know many talented musicians and singers who wish they were funnier on stage.

So why not do both?

The following is a list of people who’ve made the best of both worlds, combining comedy with music to transform lyrics into punchlines.


(Image source)

The Lonely Island

Andy Samberg, Akiva Schaffer and Jorma Taccone have taken the comedy-music scene by storm.  Again using YouTube as their main distribution network, their songs “I’m on a Boat,” and “Jizz in My Pants” have been watched close to 100 million times combined.  It would really liven up parties if you could find these karaoke songs online.  And these are just two of the songs featured on their 19 track debut album “Incredibad.”  From junior high students in Berkeley, California, to super-successful Saturday Night Live contributors, the comedy trio are creating music that rivals “legitimate” pop songs in popularity, collaborating with the vocal talents of T-Pain and Justin Timberlake.  And thank goodness!  There were several years there when I was worried Saturday Night Live would never be funny again.  Well done boys.


Weird Al Yankovic

Weird Al’s been pumping out weird song for decades.  His musical parodies of pop culture and hilarious videos have helped him sell 12 million albums worldwide, “more than any comedy act in history.”  There was a time when you knew you’d “made it,” based on whether or not Weird Al put on a “You” costume and re-shaped your songs into something a little more, bizarre.  Nearly thirty years into his career, Weird Al’s remake of Chamillionaire’s hit “Ridin’ Dirty” has shown us that the curly-haired accordion-playing, film acting, music producing, singer-songwriting clown has still got it.

Steven Lynch

Stephen Lynch’s dream of becoming a comedic singer songwriter was ignited after watching the movie “This is Spinal Tap.” Quickly developing into one of the best in the business, Stephen Lynch’s sold-out live shows, eight albums, including his Tony-nominated performance of the hit Broadway musical “The Wedding Singer,” and hilarious Comedy Central Specials have amassed a loyal fan base of Lynch lovers around the world.


Adam Sandler

Speaking of “The Wedding Singer,” Adam Sandler’s rise to stardom began in the early 90s as a cast member of Saturday Night Live. His character Opera Man was a popular guest on the Weekend Update, and comedy hits like The Chanukah Song and Lunch Lady Land still make me laugh to this day.


Flight of the Conchords

I first saw New Zealanders Bret McKenzie and Jemaine Clement at the Just for Laughs Comedy Festival in Montreal, where they performed their quirky folk parody tune “Alby the Racist Dragon.” They have since been showcasing their hilarious songs in festivals and winning comedy awards all over the planet, and you can now watch their television show “Flight of the Conchords” on HBO and Comedy Central. If you haven’t seen the show yet, I highly recommend that you watch their half-hour HBO special, “One Night Stand” first. You can find most of this brilliant performance on Youtube, just look for the clips where Jemain is wearing the blue t-shirt with an Elk on it.


Jack Black

Jack Black has been cracking up audiences with his theatrical singing performances and his absurd lyrics for close to fifteen years as part of the comedy music duo, Tenacious D. Along with guitar player and vocalist Kyle Gass, Black combined the musical forces of Dave Grohl, Page McConnell, Warren Fitzgerald, and Steven Shane McDonald to produce their first album, which achieved platinum status in the U.S. Here you can see Black at the Oscars, singing alongside comedy legend Will Ferrell.

Dimitri Martin

Comedians like Steven Wright and Mitch Hedberg made themselves famous with their awkward demeanours and their hysterical set-up/punchline joke formats. I have always loved this style of comedy, but after twenty-five minutes or so, you can become tired of hearing the comic always hitting the same note, with the same rhythm, over and over. An effective solution to this is to have background music playing during the routine. This gives the audience time to digest the imagery of the joke, while giving the comedian time to get into the next one without having awkward silences in between. It also manages to create a funnier vibe. Mitch Hedberg had “Chuck on base” during one of his hour-long comedy albums, and two of my favourite comedians, Zach Galifianakis and Dimitri Martin both employ this technique when performing standup. Well, actually Zach sits as he tells jokes and plays piano, Dimitri plays acoustic guitar. This clip was shot before taping his new Comedy Central show entitled “Important Things with Dimitri Martin.” He was taking question from the studio audience, and he chose to answer them with cleverly-improvised songs.


Denis Leary

I was in high school when Denis Leary’s comedy album “No Cure for Cancer” came out. My friends and I would listen to it over and over, to the point where we couldn’t go five minutes into a conversation without quoting one of his rants. At the time he was the first “angry” comedians I had ever experienced, and his album was an inspiration to get into standup myself. Funny thing now is that I’ve acquired more of a taste for Denis Leary the actor/writer/creator of the television show Rescue Me, where his character stays true to the song that helped make him famous.


Rob Paravonian

I had the pleasure of opening for Rob when he performed in Montreal last year. An overall fun guy, Rob’s been playing music since the age of six. Born in Illinois, he began making people laugh for a living while attending USC in Los Angeles. First starting out as a comic, he would play his guitar while waiting to get on stage at the open mics. The funny songs he created would eventually make their way onto the stages along with him. He has since moved to New York, and he tours all over the U.S. clubs and colleges with his guitar, poking fun at the music industry through songs and jokes. The following clip went viral on Youtube, earning his “Pachelbel Rant” six million views in six months.


The Doo Wops

Based in Toronto, Canada, John Catucci and Dave Mesiano are two Italians who’ve toured the world with their hilarious songs and ridiculous antics. I’ve opened for them during their last three visits to Montreal, and every single show was sold out and nothing short of spectacular. With John on vocals and Dave on guitar, the Doo Wops’ music will stick in your brain like a slice of prosciutto wrapped around a melon. John is also a fairly decent poker player.


Jon Lajoie

Born and raised on the South Shore of Montreal, Quebec, Jon Lajoie made excellent use of the internet to become famous by posting his rap video “Everyday Normal Guy” on YouTube. Millions of viewers passed his songs around which allowed him to start touring live. His fans love his stuff so much, he barely needs to open his mouth during live performances as everyone sings along with him. Even comedy great Will Ferrell and Saturday Night Live head writer Adam McKay have admitted to being Lajoie fans.


Honorary Mention: The Dan D Lyons

There are of course many others out there who’ve made people laugh through song, but for the simple reason that one is my roommate and the other is a good friend of mine, my honorable mention goes out to Tim Rabnett and Mike Paterson, two Montreal standup comics who when joined together on stage and strapped with instruments become the musical comedy duo, The Dan D Lyons.


Oh, and before all the “Hey!  You forgot ____ and ____!  And what kind of fool leaves out ____?”  begins, feel free to leave your favorites in the comments department.


Posted by Anony-mouse 15. June 2009 at 12:45 pm :

Hey! You forgot Tim Minchin and Roy Zimmerman! And what kind of idiot leaves out Bill Bailey?

Posted by Testaclese 15. June 2009 at 1:23 pm :

Another vote for Tim Minchin. Funny songs for smart people.

Posted by MMcLaughlin 15. June 2009 at 1:35 pm :

I’ve seen a few of these before, but have saved the page to watch them all (later this evening). Great collection, I hit the reddit button, dugg, a tweet & stumbled

Posted by Gen L 15. June 2009 at 3:01 pm :

Love Jon Lajoie and Andy Samberg

Posted by Pete 15. June 2009 at 3:08 pm :

The picture at the top of the page is of Zach Galifianakis. Good luck finding any mention of him in the list. Big shiny gold star for Dan.

Posted by Kash 15. June 2009 at 4:23 pm :

Andy Samberg is awesome

Posted by Andy 15. June 2009 at 8:34 pm :

Definitely agree with Tim Minchin and Bill Bailey, they’d be top of my list easily. Although some of these are very good – Jack Black in particular.

Posted by Joe Barnosky 15. June 2009 at 8:39 pm :

Seriously, Tim Minchin. Youtube him now.

Posted by Dan 16. June 2009 at 3:02 pm :

@ Pete
Thanks for the big shiny gold star buddy! But no luck will be needed in finding good ‘ole Zach, as his name appears as clear as day in the Dimitri Martin paragraph. You’re right though, it was pretty well camouflaged amongst all those other words. Do I still get to keep the star?

Posted by Hog Whitman 16. June 2009 at 8:12 pm :

Other than Leary, Yankovich and Sandler (he had at least one good one), I’m just not feeling it.

Posted by bob 17. June 2009 at 4:50 pm :

what about bo burnham

Posted by Paronomasiac 29. June 2009 at 3:34 pm :

Found this through stumbleupon, and I have to ask: What about all the truly great comedian/musicians of times gone by? Tom Lehrer, Frank Zappa, Steve Allen, Spike Jones . . . Sure, you may not be able to catch them on youtube, but the live recordings of their shows were phenomenal. Most of their material has aged well enough to still be uproariously hilarious today.

Posted by tomlehrerfan 29. June 2009 at 5:27 pm :

What about Tom Lehrer? Sure, he was popular quite a while ago (the 60’s and 70’s), but he’s still hilarious…want to laugh? Listen to “New Math” or “The Masochism Tango”.

Posted by blackswandown 9. July 2009 at 9:48 am :

how about kelvin glass? youtube him. Or rob hall from curdle? he was doing it back in the 80’s! not as well known as the above, but definitely deserve to be.

Posted by heff 11. January 2010 at 5:09 pm :

While I agree Lehrer and the like must be on there, the new guy you forgot is Bo Burnham!! He is basically a socially awkward Stephen Lynch, and funny as hell to boot!

Posted by JAM 11. January 2010 at 6:46 pm :

okay, they were canadian, and a little risque for mainstream audiences, but maclean and maclean were some of the funniest frigging guys….

Posted by Calypso 11. January 2010 at 10:03 pm :

Tim Minchin and Bo Burnham.
Shame on you.

Posted by Psssh 13. January 2010 at 5:36 am :

Everybody knows that Leary is a joke-stealing poser.

Or as Bill Hicks put it, “I stole his act. I camouflaged it with punchlines, and to really throw people off, I did it before he did.”

Posted by Dale 18. January 2010 at 11:53 pm :

I gotta be another one of those. Shame on you for the serious lack of Tim Minchin on this list. He’s better than at least half of these guys.

Posted by Stu 23. March 2010 at 10:51 pm :

Another vote for the genius of Tim Minchin and Bill Bailey having had the pleasure of seeing them both live & laughing my ass off the entire time! Also added to this list should be Corky & The Juice Pigs, Dudley Moore (watch him sing ‘Jump’ on youtube… I challenge you not to be split your sides laughing)… There are a few more obscure artists & bands that deserve mention but…. another time! 😉

Posted by bob 17. January 2011 at 10:41 pm :

Bo Burnham isn’t on there. List is null and void.

Posted by pwaitr 18. January 2011 at 1:13 am :

Look, I like all these guys but lyrically not even Lil Wayne can get on Bo Burnham’s level of intricacy and his jokes are stacked 2 even 3 to a line fairly consistently. Best Comic/Rapper Alive. Shits on all these guys.

Posted by Bo Nana 9. March 2011 at 5:12 pm :

Did anyone mention Rodney Carrington?!

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