Funny Music Friday: The sharp, soulful wit of Henry Phillips

Every other Friday, we’ll explore one of comedy’s underrepresented — but thriving! — genres: musical comedy. From artists who cut their teeth in comedy clubs with a guitar and a dream, to artists who make funny with full bands backing them; from going behind the scenes of classics like from the Dr. Demento show, to uncovering the deepest corners of YouTube, we’ll highlight a hilarious musical comedian who’s out there making the world laugh with expertly crafted tunes.

Once again, we delve into the long and storied career of a comedy musician who’s made an indelible mark on the scene. This week we’re focusing on Henry Phillips, an over-20-year veteran of the funny music genre.

A Los Angeles native, Phillips began performing with the intent to make it as a studio musician — but one night, to help cheer up a friend, he picked up a newspaper and sang the dire headlines of the day, ending each “verse” with the refrain: “But what do you want me to do about it?” On a whim, he tried it onstage and killed, bringing the house down. Phillips hasn’t looked back since.

In 1997 he released his first album, On The Shoulders of Freaks:

He produced several more albums over the next few years, each displaying his knack for finding the ridiculous in everyday situations. His releases, a mix of either live tracks or studio recordings, would often highlight his penchant for playing the underdog – the hapless individual to whom the hilarious situations would often occur. It’s a character he’s cultivated well within his act.

In 2010, he parlayed his experiences as a traveling troubadour in the film Punching the Clown. In this semi-autobiographical feature, Henry plays…well, basically himself, living out of his car moving from gig to gig until happenstance propels him quickly to stardom – and a miscommunication propels him just as swiftly out of it. The film picked up the Audience Award at the Slamdance film festival that year, and just this February he released a sequel, Punching Henry, where our perpetual loser hero tries to land a sitcom, but instead becomes the joke rather than the one telling them.

Through his music and movies, the one thing that seems to ring through is Phillips’ earnest sincerity. The films may be autobiographical (to a point) but he humanizes the character of Henry so well you can’t help but root for him, much as the listener does with his songs. Not often does one get compared to both Tom Lehrer and Billy Joel, and have both feel like spot-on descriptions.

These days, Phillips is pulling double duty as both performer and actor. He’s racked up appearances on Comedy Central Presents, Drunk History, and Jimmy Kimmel Live, as well on multiple episodes of HBO’s Silicon Valley (as creepy server-monkey John). He also has a series of YouTube videos where he plays another caricature of himself, attempting to teach others how to cook, in “Henry’s Kitchen.” Each episode features the dry, subtle humor of a man totally inept at actually teaching others how to talk, let alone make a meal, and smacks of the familiarity of every awkward YouTube amateur. The background music is Phillips, as “Jose Suicido,” who released an album titled Let’s Get Suicidal to accompany the clips (inexplicably, he’s somehow got a cookbook as well).

Though he’s got his hands in a lot of other projects, it’s with his comedy music where Phillips really shines. His most recent album/special, Neither Here Nor There, was released last year on Vimeo and is a fantastic example of the troubdour’s work. Familiar jokes and songs from the past are included with new stories and updated versions of classics (such as “What Do You Want Me To Do About It” and “Oops!,” amended to keep things topical) with a style and flare all his own. Beautiful melodies and instrumentation from a true master on the guitar, coupled with sarcasm and a deadpan delivery of realism behind the twinkle in his eye, makes every performance a hilarious stand-out.

Phillips is currently on tour throughout the US and UK, beginning this weekend as the Guest of Honor at FuMPFeST in Chicago, IL. You can find his albums at Amazon, iTunes, and the like, or pick them up directly from his website, where you can also check out his video series’ and tour dates.