20 Great Musical Comedians

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They go by different names: Musical stand-up comics, comedy-folk duos, two-man novelty bands, or perhaps they’re simply comedians with a penchant for songwriting. Call it what you like, but using music for comedic purposes is nothing new. Writing a joke and writing a song may seem at opposite ends of the storytelling spectrum, yet time and again musical comedians have shown songs are an ideal form ripe for the laughing.

Some musical comedians play music their entire set while others may pick up instruments here and there to punctuate their more typical joke telling, but whatever the case may be, musical comedians have provided audiences with a unique type of wit. Whether it’s a clever way to get their voice across and differentiate them from other stand-up comics, or a way to make fun of a song’s form a la Lonely Island, here are some of the best the business has ever seen, in no particular order.

1. Tom Lehrer

A precursor of sorts to Lonely Island, Lehrer’s work exploded song forms. Drawing upon the period’s popular music, he wrote his own satirical versions, adding in sharp commentary about the 1960s. With his rollicking piano and vocalist styling, his music softened the blow to many of his politically astute points. Singing about everything from censorship to Nazi scientist Wehrner von Braun, who drew Lehrer’s ire in a biting song lambasting the man’s wartime activities, it all seemed funnier—and easier to take—thanks to Lehrer’s music. The comedian was particularly adept at breaking down lyrics to play with an audience’s expectations, briefly delaying a syllable in order to land a punch line. Released in 1965, Lehrer’s most popular work That Was the Year That Was remains a classic comedy album to this day.

2. Garfunkel and Oates

Kate Micucci and Riki Lindhome are each comedians and actresses in their own right, but together they’re a formidable team. A counterbalance to many of the male musical comedians out there, they provide a female’s point of view on all manner of things from pregnant women (those smug jerks) to figuring out the difference between hand jobs and blowjobs. Their sweet demeanor and folk song structure contrast much of their subject matter, so don’t let their wide-eyed, seemingly innocent look fool you. Theirs is an honest take on life as a 21st century woman. The two became so popular they landed their own TV show on IFC, which followed their struggles to break into stand-up by way of their music.

3. Bo Burnham

At a whopping 24 years old, Burnham has already blazed a serious trail in stand-up. With four comedy albums under his belt, Burnham has the kind of career one expects from a veteran comic. Make no mistake about it: Burnham is a veteran, even if his age suggests otherwise. In addition to other non-traditional musical bits like when he knocked a bottle of water off his stool and then danced to a pre-recorded song informing the audience he meant to knock the water over in 2013’s what, Burnham integrates guitar and keys into his set. As a result, his show seems more in line with the variety kind than any stand-up special. Oscillating between sensitive and asshole, Burnham finds the comedy in between, exposing things audiences may think but never say. His song “Sad” talks about genuinely horrible things, but the way his stage presence sells the bit makes the difference. In a lot of ways, Burnham is comfortable making fun of the comedian type who exploits pain and suffering for laughter.

4. Spike Jones

Like other musical comedians in the late 1930s, Jones began as a musician before branching out into comedy. A studio band percussionist, he also performed on radio shows, where he realized that bigger sounds were needed to emphasize or punctuate a moment. He began integrating sound effects and other wacky instruments into his music, which set him apart from other performers at the time. One of his more famous “novelty” songs was a special rendition of the romantic “Cocktails for Two.” Jones turned the croon about a lovely evening out on its head with horns, bells and percussive effects, all of which delighted listeners with their whimsy. Accompanied by his band the City Slickers, Jones went on tour as the Musical Depreciation Revue in the early 1940s, playing “Cocktails for Two” and his other hits like “Der Feuhrer’s Face.”

5. Stephen Lynch

Armed only with his guitar, Stephen Lynch has a stage presence that at the outset may look like your typical singer-songwriter, but his songs and comedy inevitably turn dark. His strongest humor oftentimes comes from the juxtaposition between his melodic strumming and the lyrics’ increasingly messed up humor. In one of Lynch’s more popular songs, “Lullabye (The Divorce Song),” he softly and sweetly sings about divorce and all the reasons why his wife left him, each one becoming more and more awful and as a result hilarious. With big hits like Little Bit Special in 2000 and the live album Superhero in 2003, Lynch had huge momentum. His follow-up albums haven’t hit the same mark his earlier work set, but he continues offering his trademark musical lampoons.

6. The Smothers Brothers

Usually seen dressed in matching suits, Thomas and Richard (Dick) Smothers may not have seemed like comedians at the outset. Their straight-laced appearance fit their sweet harmonies and folk melodies perfectly, aligning with other big folk acts at the time like Peter, Paul & Mary. The fun began when their songs often devolved into a fight. Watch their classic “My Old Man” and see how a seemingly sweet song quickly devolves into carefully controlled chaos. “My old man is a cotton-picking, finger-licking, chicken-plucker. What do you think about that?” sings Dick. “You better not make a mistake,” Tom seriously advises, hinting at the inherent wordplay. In the late 1960s, their variety show The Smothers Brothers Comedy Hour aired sharp satire aimed at the mounting political issues of the time, especially racism and the Vietnam War; despite its popularity, CBS cancelled it in 1969 due to these controversies.

7. Flight of the Conchords

New Zealanders Jemaine Clement and Bret McKenzie sing about all manner of subjects from the robot revolution to denying the fact that they’re weeping, but no matter the content, their songs all have an absurdist tone. The pair adroitly uses their nerdy, quiet personas to explore things like relationships, sexual expectations and what day of the week is best for sex, but that focus on life doesn’t stop them from singing about Bowie being stuck in space or a racist dragon. It’s all a toss-up, but it works so well thanks to their clever wordplay and catchy melodies. Their novelty songs were such a hit they were able to turn them into their HBO series by the same name.

8. Adam Sandler

Mention Adam Sandler’s name in the same sentence as “musical stand-up comedy,” and many people may jump to his classic “The Chanukah Song” and its eight crazy nights. More than a one-hit wonder, though, Sandler has a large oeuvre of comically minded songs. Between the song bits he wrote for his time on Saturday Night Live, or the songs he played exclusively for his stand-up, he’s laid a lot of ground word for today’s modern day musical stand-up comic with his one-man, one-guitar shtick. Employing funny voices or a funny spin on genres like reggae, Sandler didn’t limit himself to any one way to do musical stand-up. Many of his comedy albums released throughout the 1990s like They’re All Gonna Laugh At You! and What’s Your Name? seem more like a variety show, weaving together jokes, “scenes” and songs like the great “Food Innuendo Guy.”

9. Tenacious D

Unlike most other acts on this list, Tenacious D has a heavier rock sound that they use to full effect in order to parody and somehow still pay tribute to classic rock. Jack Black and Kyle Gass know how to play their roles, the latter straight man to the former’s wild card. And that’s what works so well for their particular style. With now-classic songs like “Kielbasa,” which has less to do with the actual sausage than what Jack and Kyle have in their pants, the pair composes some truly memorable songs that are equal parts funny and great music. Their banter in between songs helps reveal these two goofballs for the rock nerds they are. Their 2001 self-titled album became a hit among the college set, and Tenacious D followed it up with another album and film Pick of Destiny and their most recent album Rise of the Fenix.

10. Allan Sherman

A song parodist from the early 1960s, Sherman hit it big with a series of comedy albums titled My Son, the Folk Singer, My Son, the Celebrity, and My Son, the Nut. The last included the instant classic “Hello Muddah, Hello Fadduh!” sung from a young camper’s point of view as he writes his parents about the horrors of summer camp. In addition to parodying popular tunes the way Weird Al does today, Sherman also concentrated heavily on classical music; “Hello Muddah, Hello Fadduh!” is set to Amilcare Ponchielli’s “Dance of the Hours,” which provides a sweet if mischievous background to contrast the young boy’s complaints. For all his popularity as a song parodist, Sherman initially got his start as a comedy writer before discovering his talent for applying his wordplay to music.

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