In his early stand-up days, Louis C.K. also loved to direct short films on the side. In 1993, he made a black-and-white short called Ice Cream which was intended as a riff on films from the Golden Era of Hollywood. It played at the Sundance Film Festival and lead to his first major break since the short impressed the staff at Late Night with Conan O’Brien and earned him a job on the writing team. You can even see Louis at the 3:27 mark of the film as a flower vendor, though you’d probably never know it was him if you didn’t read the end credits. I love this quote from Louis made while talking about Ice Cream in an interview, perfectly summarizing just how much easier it is to release a short film in the Internet age:
“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.”