Comic singer-songwriter Henry Phillips continues to engage as a likable loser in “Punching Henry,” a sharply observed and understatedly amusing follow-up to “Punching the Clown,” the prize-winning 2009 indie in which he played a chronically luckless character modeled, and named, after himself. Mind you, it’s not absolutely necessary to have seen that earlier film for you to appreciate this one (which, like its predecessor, Phillips co-wrote with director Gregori Viens). But if you are familiar with the 2009 opus, your enjoyment here may be laced with melancholy, since it appears that Phillips — or at least his on-screen alter ego — is still going nowhere fast while doggedly chasing his dream.
As “Punching Henry” begins, Phillips remains stuck in the lower depths of show business, telling jokes and performing tongue-in-cheek tunes before small audiences (and, sometimes, aggressive hecklers) at second- and third-tier comedy clubs in flyover country. Five years after inadvertently blowing a big break in L.A., he returns to the scene of his shame at the urging of his motherly manager (Ellen Ratner), who is the bearer of remarkably good news: A high-powered TV producer (J.K. Simmons) wants to package a reality show about Phillips’ ongoing travails as an underemployed D-lister. Cable network executives warm to the pitch — “Sisyphus meets Charlie Brown!” — but insist that, even before a pilot can be planned, Phillips must attract an enthusiastic following through social media.
Unfortunately — and, yes, predictably — Phillips is the sort of unassuming schlemiel who’s quite capable of snatching defeat from the jaws of success. Indeed, a scene in which he obtains a reduction for a parking-violation fine is the closest the movie comes to allowing him any sort of clear-cut triumph.
Reprising a device from “Punching the Clown,” Phillips and Viens effectively construct their narrative as a series of episodes linked by a wryly revealing interview (conducted, in this case, by Sarah Silverman as a podcast host). The assorted vignettes run the gamut from showbiz satire to sitcom-style riffs as Phillips repeatedly endures frustration and/or embarrassment while interacting with close friends, passing strangers, and fellow performers. The funniest misadventures include heated conversations with an irate cab dispatcher (Doug Stanhope), demeaning mishaps during gigs at less-than-stellar venues, and an ill-fated attempt to impregnate, at the couple’s request, the wife (Stephanie Allynne) of his best friend (delightfully dry-witted comedienne Tig Notaro).
Phillips, who has the everyman look of a younger John Heard, is such a sympathetic sad sack throughout “Punching Henry” that it’s occasionally discomforting to watch what happens to him. But that is a major part of this low-key comedy’s charm: You’re never laughing so hard at the protagonist that you don’t feel at least a tiny bit of his pain.