11. Tim Minchin
With dark eyeliner and wild hair, the British-born Australian comic looks more like a rock star than your typical comedian. It makes sense then that his shows have more in common with a rock concert than any kind of traditional stand-up. Underneath the stage production replete at times with a full backing band and light show, Minchin’s songs are funny. Hilarious, actually. They work because of his particularly witty wordplay, rhyme scheme and ability to use both to ridicule life in the twenty-first century. In the song “Prejudice,” Minchin breaks into a rap rhythm and sings about how “Only a ginger can call another ginger ‘ginger’” before launching into the trials and tribulations of being a ginger. “Ginger,” of course, cleverly standing in for that other forbidden word starting with an “N.” Minchin put his songwriting ability to good use by writing the music and lyrics for Matilda the Musical, which went on to win five Tony Awards in 2013.
12. Zach Galifianakis
If anyone can make a living from being awkward, it’s Zach Galifianakis. Before he made it big in projects like The Hangover or his fake interview show Between Two Ferns, Galifianakis was known for his dry humor at the piano. He tinkled the ivories with a sarcasm that contrasted the soothing melodies he used as background music. Alongside traditional stand-up, he would take a seat at the piano and quietly play music while continuing to share his observations about life. Unlike other musical comedians on this list he didn’t perform true songs, but his brand of musical comedy worked well because his instrument worked like a prop that further juxtaposed Galifianakis’ already twisted comedy.
13. Demetri Martin
Where most comics on this list rely on one or two instruments, Demetri Martin employs more. A lot more. Using a ukulele, a harmonica, or even a glockenspiel at times, Martin uses these quirky instruments to augment his goofy sense of humor. Adding to this quirky style, Martin brings in all kinds of props to the stage instead of relying solely on the mic. In his 2003 special If I…, he drew out pictures and used them as site gags. Like Galifianakis, Martin at times talks over his music, using the background strumming of his guitar to share his humorous observations, but he does perform songs, too. It’s a smorgasbord, containing a little bit of everything as Martin both explores and pushes what it means to perform stand-up. He took his off the wall style to Comedy Central for the show Important Things with Demetri Martin which lasted for two seasons between 2009 and 2011.
14. Judy Tenuta
With her trademark voice and accordion, Tenuta had a brash stage personality that prodded audiences right in their funny bones. It didn’t matter if she insulted her crowds, growled out punch lines or sang lewd songs about her desires, she approached her craft with such vivacity and originality that audiences ate it up. She epitomizes “madcap.” In the stand-up special Ladies of the Night, she comes twirling out in a dress and approaches the mic, greeting her audience with “Hi, Pigs.” Whether using her accordion to punctuate her jokes or singing full songs like wanting to fall in love with the cowboy-esque Pope John Paul, she found ways to integrate music into her act and accentuate her comedy in different ways. With lyrics like “I just want a cowboy in a long white silky dress,” she took the stage as much to shock as to get laughs.
15. The Lonely Island
The comedy trio may now be known for their hilarious SNL Digital Shorts and the three comedy albums they released as a result of their popularity, but the group actually didn’t start in music. Andy Samberg, Akiva Schaffer and Jorma Taccone first grew their high school comedy group by doing short films and writing. Their sharp wit landed them at Saturday Night Live’s doorstep, where all three wrote and Samberg performed. Their unique send-up of contemporary pop, hip-hop and electronica song forms (and the celebrities they attracted to participate in their hyperbolic-absurdist fun) quickly became one of the show’s most popular elements. From the now classic “Dick in a Box” to the equally popular “I Just Had Sex,” Lonely Island created hilarious spoofs that made fun of both a song’s style as well as its subject matter.
16. Steve Martin
It makes sense that while writing for The Smothers Brothers Comedy Hour, Martin became exposed to the kind of musical comedy that would go on to influence his own routine. Hearing The Smothers Brothers and their musical guests perform, and opening for bands like The Nitty Gritty Dirt Band, Martin evolved into a versatile stand-up comic. Part of his routine involved humorous songs, including one of his most famous, “King Tut,” which details the famous Egyptian king’s funk factor. Where other musical comedians favored a guitar or piano, Martin tended to go for the banjo, using it to play songs as well as bits. One in particular involved performing “Dueling Banjos” for the crowd with the second banjo noticeably absent. It’s a moment that showcases Martin’s comedic timing and musical prowess to full effect. Despite being one of the leading stand-up comics in the 1970s, Martin eventually left that world behind to pursue other acting projects, but he continues to play music, especially bluegrass, to this day.
17. Eric Idle and Neil Innes
Together, Idle and Innes are perhaps best known as Dirk McQuickly and Ron Nasty, respectively. The two men created The Rutles, the famous Beatles’ parody band. Initially, The Rutles performed as part of Rutland Weekend Television, Idle’s post-Python project with Innes, which included sketches and other comedic songs, some with a humorous political bent and others absurd in the vein of Monty Python. For instance, the show’s first episode features a song about a man who stars in dirty movies, but in all other aspects of life looks like your average guy. The Rutles were their biggest hit, however, and eventually the parody group filmed a TV special called All You Need is Cash and actually went on tour. The pair’s story ends on a sad note, as Innes filed a lawsuit in 2014 against unpaid royalties for music used in the theatrical production Spamalot.
18. Victor Borge
Known as The Clown Prince of Denmark, Borge had a teasing wit that always seemed one step ahead of everybody else. Oddly enough, it was a quickness he achieved mainly by playing dumb. He often pretended to be confused, like when he would approach his piano and exclaim it only had one big black key for him to play before realizing he needed to open its cover. Often appearing in a suit or a tux, his poised, well-dressed exterior belied the crackling wit underneath, which emerged in both physical and intellectual ways. At times Borge waxed comedic about Mozart or Beethoven, at others he seemed very much the elementary school class clown. In between stand-up bits where he read audiences stories including every piece of punctuation, he tended to play a mix of classical pieces. Not one to let a funny moment go to waste, he would often interrupt his playing with explanations or stories about the composer or composition. It may seem high-minded, but Borge made it all accessible, showcasing why he isn’t the average musical comedian. He was a musical prodigy who saw life’s humorous side.
19. Henny Youngman
If you’ve ever heard the one-liner, “Take my wife…please,” then you’ve heard Henny Youngman. He may have started out as a musician in the mid-1930s, but his sharp tongue quickly brought him other opportunities. Rather than choosing between music and comedy, Youngman wove the two together, playing violin in between his routine. The instrument’s almost wistful sound contrasted his straightforward, irreverent sense of humor, and made for a distinct act at a time when comedians tended to build up a story over time. Youngman instead fired one-liner after one-liner, landing numerous jokes in a short span of time and earning him the nickname “The King of the One Liners.” With a career spanning seven decades, Youngman proved he had staying power despite the changing nature of comedy. In fact, his approach to stand-up influenced some of the industry’s greats, including Rodney Dangerfield.
20. ”Weird Al” Yankovic
No list would be complete without the man himself, Weird Al. Regarding that old question about the chicken and the egg, it’s up for debate what came first for Weird Al: music or comedy. His ability to parody popular songs into memorable new ones is a talent unto itself. Performing since the early 1980s, he’s parodied some of the biggest names in music, including Michael Jackson, Nirvana and Lady Gaga. It doesn’t matter how the music industry shifts, he continually offers listeners a fresh take on the radio’s most popular songs. It’s no wonder then that he’s remained such an iconic and beloved figure to this day, known as much for his funny music videos as his songs. Despite Weird Al’s many Grammy awards and other accolades it took his 2014 album Mandatory Fun to earn him the number one spot on the Billboard 200 list for the first time in his career.
Amanda Wicks is a writer specializing in comedy and music, and now the place in between where they make sweet musical laughter. Follow her on Twitter @aawicks.