Punching the Clown is another film with a protagonist desperate to make a living in the entertainment industry. In this case, the lead is Henry Phillips (who also co-wrote the screenplay) playing a variation of himself. Billed as a "traveling modern troubadour," Phillips struggles as much as that description might lead one to believe. Trudging from town to town in search of the next over-lit pizza parlor or seedy bar that will supply the next few dollars to keep the car running toward the next thankless, humiliating gig, Phillips eventually finds himself at that stopping point that many a wannabe has most likely faced. Fed up and broker than usual, Phillips takes his brother (Matt Walker, in an amusing bit) up on an offer to crash on his couch in L.A. in the hopes of landing steady income, most ideally in the form of a record offer, which is nearly unthinkable for someone who sings what most people would dismissively call folk.
Punching the Clown is a euphemism for masturbation, and the film has the potential to become just that: another self-congratulatory inside-Hollywood circle jerk. But Phillips is a poignant presence, as his mildness has a lonely urgency. Soft-spoken, fair and blond, with an average build and demeanor, Phillips is the near-embodiment of the sort of person you picture L.A. swallowing whole, and his songs play to this assumption. Phillips's music has a sly anger, a frustration with presumed perceptions of mediocrity. Phillips opens his show as a fairly transparent James Taylor wannabe (his agent wants to bill him as "James Taylor on Smack" until it's explained that Taylor actually did have drug problems) only to abruptly segue into blatantly hostile, desperate, horny thoughts that might startle anyone inclined to condescendingly write Phillips off as a "nice guy." Punching the Clown can be too cute, and it has an extremely expendable subplot where Phillips is misread as a bigot, but it's a quietly sad portrait of just barely getting by.