Louis C.K.’s decision to make Tomorrow Night, his never-released, independently financed first feature from 1998, available for $5 on his website, is the kind of offhandedly iconoclastic gesture that has endeared the comedian to his fans (a group to whose ranks I belong). Nothing C.K. makes quite fits into the categories that pre-existed it, so why should his marketing and distribution techniques? His F/X series Louie, now on a break between its third and fourth seasons, demolishes the barriers between stand-up and situation comedy (and plenty of other barriers, including the one between the lead character’s fantasy life and his lived reality). C.K.’s previous show, the short-lived Lucky Louie on HBO, was a less freewheeling but similarly unorthodox take on the sitcom form, a domestic comedy shot on deliberately fake-looking sets with low-quality video seemingly straight from the Norman Lear era.

C.K.’s only previously released theatrical feature, 2001’s Pootie Tang, was a bizarre blaxploitation send-up about an African-American pop-culture sensation (the eponymous Mr. Tang, played by Lance Crouther) who spoke entirely in his own nonsensical but somehow universally comprehensible patois. (This clip gives some sense of the movie’s odd rhythms and almost Situationist sense of the absurd.) While Pootie Tang puzzled most audiences at the time (and has since been semi-disowned by C.K., who says the film was recut by the studio to such a degree that he no longer considers it his), it’s attracted a loyal cult following over the years. Viewed now, it’s intermittently funny—I’ll always treasure the scene where the lady killer Pootie seduces a character by sensuously rubbing handfuls of cherry pie over his face and neck as R&B thrums in the background.* But the film is valuable mainly as a document of its director’s early ambition and originality: One thing you could never accuse this defiantly strange movie of is fitting too neatly into a genre or industry slot.

That’s twice as true of Tomorrow Night, which, viewed 16 years after its creation in a format that didn’t exist when it was made, testifies to the degree to which the then 31-year-old Louis C.K. thought of himself as a filmmaker. Tomorrow Night is, in many ways, a piece of juvenilia, the arty thesis project of a guy who wasn’t in film school (C.K. has said that he would have liked to study filmmaking at N.Y.U. if he’d had the high school grades to get in). But it’s the opposite of a slapped-together lark: Rather, it’s formally experimental, thematically complex, and made with tremendous attention to craft. Shot on black-and-white 16 mm film in New York City with a cast made up of many of the rising comic talents of C.K.’s generation (including, in wordless cameos, Amy Poehler and C.K. himself), Tomorrow Night displays a sureness of hand and a level of tonal control that’s far removed from the everything-but-the-kitchen sink shagginess of many comic directorial debuts.

The story—and despite its digressiveness and apparent discontinuity, Tomorrow Night does consist of a story, not just a bundled collection of sketches—concerns Charles (Chuck Sklar), the closed-off, socially inept proprietor of an exceptionally clean and well-run photo-developing business. Charles keeps his store’s shelves sparkling and his customer files impeccably organized, but at a cost. He has no friends to speak of, let alone a girlfriend, and treats everyone who enters his shop like an unwelcome intruder. But this demeanor doesn’t seem to deter Mel the Mailman (J.B. Smoove), an expansive U.S. postal employee who enjoys regaling the stone-faced Charles with raunchy anecdotes from his own life.

It isn’t until we see Charles come home from work one night that we first realize how far we are from rom-com-land, or for that matter from any recognizable genre category. After putting on an old-timey phonograph record, our expressionless hero gets out the ingredients for his secret nightly ritual: a tub of ice cream, a large metal bowl, and a chair. Charles, it turns out, can find sexual gratification only by sitting, naked from the waist down, in a bowl of ice cream—a harmless enough fetish, but one that C.K. films in such a way as to make the practice look both abject and transcendent. (One late scene gives us a montage of Charles’ interior fantasy world during a session of ice-cream frottage, and it’s as if David Lynch had traveled back in time to collaborate with Sergei Eisenstein.) Charlie’s clandestine fixation on frozen dairy desserts is clearly a metaphor for masturbation (a frequent subject of both mockery and meditation on Louie), but it also seems to stand in for something more. The disclosure of this unspeakable yet ludicrous secret becomes a sly joke about the cinematic deployment of secrets as both plot engines and revealers of character. Yes, we’ve been given a glimpse into this man’s most private and shameful ritual, but does that mean we know anything whatsoever about him? And is grinding one’s pelvis into a jumbo serving of butter pecan any more ridiculous than whatever the rest of us get up to behind closed doors?

The rest of the film will chronicle Charles’s ongoing sexual misadventures, from a humiliating date with a cartoonishly vulgar hot-pants-clad tramp named Lola Vagina (Heather Morgan) to an even more ill-advised liaison with an elderly client at the photo store, Florence (Martha Greenhouse). The unhappily married Florence spends her days complaining on a park bench to a housewife pal (Rick Shapiro) whom she seems not to notice is actually a man in really bad drag. In a parallel plot, Florence’s naive son Willie (Greg Hahn), who’s been deployed with the Army for 20 years, tries to figure out why his mother has never answered a single one of his letters. As it turns out, two of his fellow soldiers (Robert Smigel and Steve Carell) have been throwing Willie’s outgoing mail away for decades, a prank they confess to with hoots of cruel laughter filmed in grotesque close-up.

Though it has no shortage of funny moments and strong comic performances, Tomorrow Night seems far less invested with making the audience laugh than it is in upending our expectations, dislodging our received ideas about what a film comedy should be. It’s a chilly, slow-paced, at times deliberately alienating movie that nonetheless manages, by the end of its not-quite-90-minute running time, to touch on quite a few of the great mysteries of human life: loneliness, friendship, marriage, old age, death, the desire for a child. And throughout, C.K.’s grasp of and facility with film-historical tropes is one of the movie’s chief sources of delight. When Charles dials the number of one client whose photos are overdue for pickup, C.K. cuts to an interior straight out of an old Hammer horror film, where we see an old-fashioned phone ringing next to an inert, bloody gloved hand, a crystal decanter, and a box of dominoes. The identity of that hand’s apparently dead owner, like the connection between this gothic B-movie universe and the everyday reality Charles inhabits, is never explained. The whole joke is that, through the magic of montage and directorial whim, such divergent worlds can unproblematically coexist in the same story.

Along with David Lynch and Eisenstein, there’s some John Cassavetes influence discernible in C.K.’s method, and maybe a touch of John Frankenheimer, too, along with a generous dose of classic Hollywood. The imaginative original score by Neal Sugarman nimbly pastiches the style of old-fashioned orchestral scores from various genres, at one point including a series of harp arpeggios straight from the dream sequence of a ’40s melodrama. Tomorrow Night feels like the work of a curious young filmmaker taking cinema apart to figure out how it works, tinkering under the hood. Though his innovative TV show and punishing stand-up schedule are keeping him more than busy enough for now, C.K. has made clear that he would be interested in making another feature film someday, perhaps self-financing it with the proceeds from the online sale of Tomorrow Night. If for no other reason than that, the $5 he’s charging for this curious comic artifact seems like money well spent.

Correction, Jan. 31, 2014: This article originally stated that the woman seduced by cherry pie in Pootie Tang was played by Jennifer Coolidge. Coolidge’s character was not in that scene. (Return.)

