The 10 Best Directorial Debuts by Comedians

Last month we assembled a gallery of thirty-two directorial debuts by comedians and comedy writers in the wake of the enormous success of Jordan Peele’s debut, Get Out. We promised a follow-up ranking the ten best debuts from that list, and Get Out has only received more Oscar buzz and an extra couple million dollars over the past two weeks, so it’s as appropriate now as it’s ever been
It’s worth noting that among these higher-achieving films (either in box-office dollars or critical/cult opinion), the three that are not straight forward comedies were both made in the past few years—which is indicative of our changing perceptions of comedians’ output on the whole. Pigeonholing, it seems, occurs less often, and it’s less surprising than ever for a comedian to take on a more serious role.
Regardless of tone, however, here are the ten strongest outings by comedians directing their first movie.
MacGruber, Jorma Taccone
I know this seems like an inauspicious start to this list, but stay with me. I will be the first to admit that the reoccurring “MacGruber” SNL sketch—also created by Taccone—was not for everybody. Though it pulled through on the strength of committed performances from Will Forte (who, to his credit, resisted participating in the initial sketch on the grounds that it was way too dumb) and Kristin Wiig, this bizarre MacGyver parody was the last sketch you’d want to watch for ninety minutes. When a MacGruber movie was announced, it felt like the first SNL film in ten years would be more It’s Pat than The Blues Brothers. But it wasn’t. With the sleep deprivation from producing a feature length film alongside a weekly TV show reportedly inspiring the film’s more insane sequences (like the “celery-in-ass” distraction), Taccone had the film lean so far into action movie clichés that it ended up being undeniable. What resulted was one of the most effectively hilarious films in recent memory. With MacGruber routinely tearing throats out, fucking his ghost-wife (Maya Rudolph) in a graveyard, assembling and then losing a team of WWE wrestling stars in about five minutes, and battling a villain named Dieter Von Cunth (Val Kilmer), it was no surprise that critics despised this film and audiences stayed away. That’s a shame, because as far as belly-laughs go, it’s pretty hard to beat “just tell me what you want me to fu-uck!”
Monty Python and the Holy Grail, Terry Gilliam and Terry Jones
It sucks that some of the shine has been taken off Holy Grail by its own overwhelming ubiquity. Nowadays, when we hear a “flesh wound,” a “ni!” or a “huge tracts of land,” our first thoughts are often of having full scenes repeated to us by clueless, obsessive nerds. Or, in my case, of repeating full scenes to people as a clueless, obsessive nerd. But, if you try and distance yourself from the over-saturation factor, and revisit the film after a few years, you’ll find new jokes that feel as fresh and hysterical as the ones we all know. Holy Grail is, indeed, the most densely packed comedy in the Python canon. There are so many jokes in this movie, and it’s surprising how easily we forget that, considering its reputation. If you’re truly and irreversibly burnt out from this movie, watch it again with commentary, and discover the second level of appreciation that comes from the inventiveness with which it was made. It certainly doesn’t look like a $400,000 movie, and it’s delightful to discover which of the gags (like the coconut halves) were born from a need for low-budget workarounds. The first-time co-direction from onscreen performer Terry Jones (who only sporadically directed after Python broke up) and lone American Terry Gilliam (who prolifically bent Python’s cinematic style into his own unique brand of nightmarish fantasy) moves with a surreal efficiency.
Sleepwalk with Me, Mike Birbiglia
Birbiglia thoroughly outdid his debut with its improv-themed follow up, Don’t Think Twice, and this first film is not nearly as devastating, but it benefits from the audience’s base understanding of the art form. Sleepwalk with Me, adapted from Birbiglia’s stage show and memoir, doesn’t spend time explaining stand-up, and the movie moves briskly as a result. The formal playfulness (fourth wall breaks and sudden dream sequences) and transparent autobiography (Mike is “Matt Pandamiglio,” while Marc Maron is “Marc Mulheren”) led many to compare it to Annie Hall and declare Birbiglia as the next Woody Allen. But, as a filmmaker, Birbiglia has more in common with Allen’s more deliberate peer, Albert Brooks. The film’s emotional acuity is largely thanks to Birbiglia’s strength as an actor, and to date it is still (along with Obvious Child) the most refreshingly honest portrayal of life as a stand-up.
Other People, Chris Kelly
If you’re looking for a devastating debut, look no further than SNL head writer Chris Kelly’s dramatization of the death of his mother. Jesse Plemons plays Kelly’s stand-in, a UCB improviser named David who moves back to Sacramento to be with his dying mother (a really, really good Molly Shannon). The cast is packed with excellent turns, from Bradley Whitford as the dad who quietly disapproves of his son’s sexuality, Zach Woods as David’s sort-of-ex, John Early as David’s one hometown friend, and child-actor J.J. Totah as Early’s spectacularly flamboyant younger brother. But Plemons and Shannon simply can’t be topped in this movie, and the physical effect of her illness on both of them is incredibly hard to watch. Kelly—additionally lauded as a writer on Broad City—answers the question of Shannon’s fate by starting the movie with her long-expected death, but then immediately shows off the film’s morbid humor by having her receive a clueless voicemail hoping she feels better. Melodrama is nimbly avoided at every turn, but that doesn’t stop the fucking waterworks when the time comes. I cried so hard at this movie I couldn’t really believe it.