For better or worse, there is humor to be found in everything. Every awkward moment in the elevator has a sliver of absurdity. Every emotionally-draining funeral has the potential for some granule of lightheartedness. You just have to be fearless or crazy enough to delve into that void.

In films like Annie Hall and Broadway Danny Rose, Woody Allen created comedy from the lives of characters in seemingly bleaker moments. Around the mid-’80s, Allen was putting out about a movie a year. One movie buff was already enjoying the absurd components of Allen’s existential world view.

At the age of 17, Louis Szekely, better known to most as Louis C.K., was attempting to fill five minutes of open mic time with two minutes of jokes. That same year, with the help of friends and family, he directed his first 16mm comedy, Trash Day, a film about thieves stealing garbage. By 1993, he had completed his third 16mm short film, Ice Cream, a 13 minute deadpan comedy starring himself as well as stand-ups Neil Brennan, Laura Kightlinger, and Craig Anton.

Needless to say, 1993 filmmaker tenacity was worlds apart from 2016 filmmaker tenacity. In a 2010 interview Louis C.K. recalled, “When I made that thing, you had to actually write to a film festival. Like you had to go to the library and get a book that has all the film festival addresses in it. You had to write to film festivals and say, ‘Can you please send me an application.’ And all these film festivals would send you applications and then you make VHS copies of all your stuff, of your film, and send it in, and hope you get in.”

He did. Ice Cream wound up playing at the Sundance Film Festival and the Museum of Modern Art that following year. After that the film was on European television and U.S. cable networks like IFC and Bravo. More importantly, Louis C.K. included Ice Cream as part of his submission to be a writer for Late Night with Conan O’Brien. While his work in stand-up helped get his foot in the door, it was his film work that caught the attention of O’Brien and former head-writer (and future Triumph the Insult Comic Dog) Robert Smigel to land him the job.

A few years ago, Louis C.K. released his 1997 feature debut, Tomorrow Night, on his website for five dollars. The absurd film, which made its 1998 premiere at Sundance but never secured distribution, revolves around a glum camera shop owner who dates a nymphomaniac but finds himself attracted to a lonely old woman. Shot in black and white like his short films, Tomorrow Night employs some experimentalism and the familiar neuroses that one would find in a Woody Allen film, alongside groin grabbing scenes you might find in a Troma film. Even though the film is an uneven work, as a curiosity it’s intriguing to watch as a piece that would inform Louis’ later works.

Louis C.K.’s second film, on the other hand, stands alone as a surprising cult classic. Based on a character from The Chris Rock Show (a show Louis C.K. also wrote for), Pootie Tang is a slick haired folk hero who speaks in mostly gibberish like “Sa Da Tay,” “Wa Da Tah,” and “I’m going to sine your pitty on the runny kine!” There are extended scenes of Pootie dodging bullets and whipping his foes with his secret weapon, a belt passed down to him by his father.

Before it had a cult following, Pootie Tang was a summer comedy that floundered against the heavyweight competition of fast and furious tomb raiders and green CGI ogres. Whereas Louis C.K.’s previous films were absurd in more of an existential vein, Pootie Tang was absurd in a silly, slapstick way. In the opening paragraph of his review, Roger Ebert echoed a sentiment shared by most critics and box office receipts, “Pootie Tang is not bad so much as inexplicable. You watch in puzzlement: How did this train wreck happen? It’s like one of those lab experiments where the room smells like swamp gas and all the mice are dead.”

During an interview with fellow comedian Jim Norton on Sirius XM, Louis C.K. lamented the whole process of getting the film made, being unsatisfied with his own work on the film and then watching it leave his hands only to be changed and chopped by studio heads at Paramount. “I had made something that was pretty unique, and nobody knew how to handle it,” he told Norton.

Almost a decade later, he wrote, directed, starred, and edited a $200,000 pilot for FX for his show, Louie, which was shot on a Red camera setup, and edited on his own MacBook Pro. The main character, Louie, is a heightened version of himself, dealing with life as a divorced comedian with kids. Thanks in part to his thriving stand-up career, Louie became a hit thanks to an indie film style and humor that recalled the self-deprecating quirkiness of Allen at his zenith.

When speaking with The Onion/AV Club’s Nathan Rabin in 2012, Louis C.K. elaborated on a phone call he received, “I got a call that Woody’s making a movie and that his casting people wanted to show him my stuff … That was a really big deal. … I didn’t care if I got the part or not. I really didn’t care. And I went back in and read it, and my heart rate was too high, I couldn’t control it, I didn’t do a perfect job, and they didn’t give me the part. But he found something else for me.”

A little later, Louis C.K received a personal handwritten letter, asking him to play another character in Allen’s film. That part was the role of Al, a louse who winds up breaking a heart in Allen’s dramedy Blue Jasmine, a film that garnered Louis C.K. numerous accolades. Speaking to Rabin, he said, “The letter was very nice and it’s my prized possession. If there’s a fire, I grab my kids and then the letter.” Spoken like a true die hard fan.