Being both a musician and a comedian (or at least someone who could loosely tie those labels to myself), I have a soft spot for artists who can deftly weave the two art forms together into something uniquely their own. While there have been countless attempts by musicians and comedians to bridge the gap successfully, those that are truly masters at their craft can create some really hilarious and musically brilliant material. Here now is a list of some the best musical comedians or comedic musicians, in no particular order.
Steve Martin – He’s perhaps the funniest man of his generation and probably the best banjo player of his generation, so of course he’s on this list. When Martin was touring the country as the most famous stand-up comedian of the mid to late 1970s, his banjo was his constant companion. Some of his funniest material, like “The Grandma Song” came out of his ability to play music and sing goofy songs. Martin had quite a bit of material that centered around his talents with the banjo.
The Darkness – It’s probably safe to say that this act struck while the iron was hot with their debut and best album “Permission to Land.” Their follow-up didn’t quite strike the same chord as songs like “I Believe In a Thing Called Love,” “Growing on Me,” or “Black Shuck.” With piercing falsettos and blistering guitars, The Darkness was 1980s glam mixed with scatological genius.
“Weird” Al Yankovic – When it comes to parodies of popular songs, no one will ever be able to compete either with Weird Al’s prolific catalog, nor the quality of work he consistently produces. His innate ability to take a song, reproduce it and change the lyrics to something much more hilarious is a skill that really no one else has ever had, or at least tried to breakthrough like Yankovic. Though he’s slowed down in recent years, he still produces top-notch content and laughs. For me, his best work will always be the late 1980s with songs like “Eat It,” “Like a Surgeon,” and “Fat.”
Tenacious D – Self-proclaimed “Greatest Band in the World,” Tenacious D is made up of the dynamic duo of actors and comedians Jack Black and Kyle Gass. What makes Tenacious D better than so many who’ve tried to write “funny” songs is that they are both brilliant musicians and comedians. This makes their material musical authentic and good, and also means their lyrical content is genuinely funny. Songs like “Wonderboy” and “Greatest Song In the World (Tribute)” showcase both Black’s singing chops and the undeniable prowess that Gass possesses for the guitar. Rumors abound that they are in the studio working on a new album, and we’ll see what’s left in the tank at that point.
Reggie Watts – Words almost fail when trying to describe what it is that Reggie Watts does in his act. He’s an improvisational musical comedian. He sings songs about everything from buying illicit marijuana to people not opening candy in the movie theater while the movie is playing. Watts has been on “Conan” several times already, and each time he gives the television and studio audience a new and more bizarre or abstract performance. He’ll scat, he’ll rap, he’ll sing Motown-inspired songs, and he’ll change his speaking voice at least six times in a set. What makes Reggie stand out is that he hearkens back to a time where comedians could be more experimental, and play around. It’s almost as if he stepped out of a rip in the space-time continuum from the 1970s.
Flight of the Conchords – Jemaine Clement and Bret McKenzie are the duo from New Zealand who blend eclectic musicality with biting comedy and sometimes plain silliness. They first came to prominence here in the United States via YouTube, but they had already established themselves in the UK on BBC Radio. HBO gave them their own show which ran for a couple seasons and exposed the world to actors like Eugene Mirman and Kristen Schaal. The Concords guest-starred on “The Simpsons” in 2010, which is still one of the greatest compliments an actor or comedian can get.