DIRECTED BY: Rick Alverson

FEATURING: Gregg Turkington

PLOT: A low-rent insult comedian who performs in a tux with a grotesque combover plays unappreciative dive bars throughout the Southwest on an increasingly surreal tour.

WHY IT MIGHT MAKE THE LIST: After another failed gig, the Comedian’s friend, a business consultant, suggests that the performer consider making his act “a little less weird.” We disagree.

COMMENTS: I appreciate a bad joke. It’s hard to write a bit that has the shape of a joke, complete with a setup and a punchline, but then fails to land properly—not something completely random, but a crack that’s just barely off, a jibe that an alien or madman might think is funny. Comedy interruptus: a joke that perversely strangles its own payoff. (Judd Nelson’s painful, sweaty monologues in The Dark Backward were built around a similar premise, although The American Astronaut‘s rambling “Hertz doughnut” bit is the most successful iteration of the trope I can think of). The nameless comedian of Entertainment deals exclusively is such jokes: he starts off with premises like “Why don’t rapists eat at TGI Fridays?” There is no possible successful punchline to that set-up; the joke, rather, is that any comedian would have such poor taste that he would even try out such a line.

The meta gets piled high in Entertainment. The Comedian’s routine, delivered from under a carefully styled oily combover, might have gone over with a crowd of irony-digging college hipsters, but he’s trying it out in working class gin joints. “I’ve traveled a long distance carrying these jokes in order to bring them here and thrust them into your fool faces,” he complains on stage, after a poke at prop comic Carrot Top earns him only a few token titters. At a country club gig, he improvises a bit where he picks up a trophy and pretends to shoot the audience, then makes fart noises for a couple of minutes before dropping the mike and walking off stage. “We’re not paying for that,” is the icy, but reasonable, response of the lady who booked him. There’s something horrifyingly Sisyphean in the idea of a comic who’s compelled to take the stage and bomb night after night in front of a disdainful crowd of miserabilist drunks.

The rest of the tour, the blank-faced Comedian stays in motel rooms or crashes on couches. He spends his free time alone taking in the desert sights (a car mysteriously upended in the middle of nowhere seems like the perfect metaphor for his own inexplicable career) or leaving pathetically mundane, never-answered messages on his estranged daughter’s phone. Between the melancholy vignettes and embarrassing failed comedy routines are plenty of surreal sights, particularly in the film’s last half hour. The tour increasingly takes its toll on the Comedian’s mental state, as events grow more and more fragmented and panicky towards the end. Public restrooms are particularly anxious locales; one of the film’s best scenes involves an ambiguous meeting with a nervous Michael Cera hanging out at an isolated rest stop, while another bathroom produces an even more scarring vision. The Comedian hangs out with a crowd who look like the Southwestern cousins of the folks from Gummo (I kept expecting a chair-bashing session to break out), leading to more odd moments. A hallucinatory guest spot on a Mexican telenovela rounds out the strangeness. Throughout, the soundtrack is omnipresent and intense, with a mix of anxious ambient drones and popular music numbers that range from the ethereal to the ironic. The overall effect is like discovering Andy Kaufman’s old Tony Clifton character has a tragic backstory and suffers from chronic depression, then watching his mental breakdown from the inside. The film is a bleak vision of complete artistic and personal frustration, yet it rings hellishly true.

Though the character is never named, star Gregg Turkington uses the same gimmick (minus the existential despair) when he performs as “Neil Hamburger” (“America’s Funnyman”).

WHAT THE CRITICS SAY:

“Somewhere on the axis where David Lynch, Paul Thomas Anderson and Joey Bishop intersect… Weirdly compelling if student-y and unfocused…”–Kyle Smith, New York Post (contemporaneous)