Punching Henry is a meta comedy about a singing comedian named Henry Phillips, played by comedian Henry Phillips, who in real life sings as part of his act. His agent gets him a meeting with a hotshot producer (J.K. Simmons), who wants to make a reality show about a sad sack loser with horrible luck who the audience just can’t help but root for. Punching Henry is much like Henry Phillips’s actual stand-up routine (he has had many Comedy Central specials)—articulate, dry, and self-deprecating.
The problems occur with Phillips himself. As an actor, he is affable but not quite engaging. And since everything, and I mean everything, is underplayed in this film, you don’t really feel anything for the guy. Emotions are barely conveyed. He surrounds himself with comedians such as Tig Nogaro, Doug Stanhope, and Jim Jefferies, but only Sarah Silverman, as a radio show host in a gratuitous and unnecessary wraparound segment, and Derek Waters, as a social media producer, have any facility with emoting for the camera. J.K. Simmons is J.K. Simmons, so he’s fine and delivers the dryness inherent in the script like a seasoned pro. But you realize this could have been a stronger film if the filmmakers had hired stronger actors. Not all comedians are. It’s a different skill set.
Anyhow, the plot trudges along as Phillips suffers humiliation after humiliation (his car is stolen 30 minutes after he arrives in Los Angeles). Some are amusing enough and some genuinely funny, such as his failed shot at providing a lesbian couple with an heir, which proves to be a highlight. Eventually, a head of steam is built up only to arrive at the life lesson to love what you do, which, in Phillips’s case, is failing.