Five Awesome Comedy Documentaries

I thought I’d take a break from the video game posts, since I just got back from a huge library conference in Anaheim (I know, I know, I’m the coolest), and had the opportunity to hang out with some awesome comedy writers and comedians at one of the panels. I dabble in stand-up myself, so it was great to commiserate with and pick the brains of people out there finding some success.

I got to thinking about how valuable it can be as a comedian to see the trials and tribulations your fellows had to go through before making it, since comedy is truly the most brutal of the performance arts, in my experience. There’s a lot to learn from watching a comedian’s act, but I love watching documentaries since they show them behind the scenes, being vulnerable or getting annoyed. Or both. Here’s a list of five of my favorite documentaries about comedians and comedy.

Basic Black: The Lewis Black Story

I love Lewis Black because he’s probably the only person other than me who’s bothered by everything. I’ll avoid psychologizing what that means for either of us, but needless to say I appreciate not being the only one who gets annoyed by the people who seemingly have no regard for anyone else around them.

The greatest discovery I made about Black while watching this doc is that he originally planned to be a playwright. Guys, I am trying to be a playwright over here. I think this means I just bought a one-way ticket on the fame train, right? Right?!


Some are born great, some achieve greatness, and some have greatness thrust upon ’em. Clearly Lewis Black was one of the former.

Believe: The Eddie Izzard Story

I’ve loved Eddie Izzard since I first saw Dress to Kill where he strode on stage in women’s clothing and launched into his routine with nary a comment on his attire. He eventually got around to talking about it, but by that time he had already won me over with his intelligent material and casually conversational delivery.

Believe doesn’t follow the typical documentary trajectory, where it’s established the subject has inherit talent that’s unrecognized, he/she finally gets their big break, falls into drug or booze addiction, and then comes around at the end. Rather, it focuses on a straight-forward delivery of Izzard’s entire career, which reveals just how difficult and disheartening the comedy world can be, and how long one can oscillate between the two when establishing a career. The narration is done by Eddie himself, which is refreshingly delivered straight with no chaser. He’s not trying to be funny while he talks about his life and career, and that highlights his determination and love for the craft.


“You’ve got to believe you can be a stand-up before you can be a stand-up.  You’ve got to believe you can act before you can act.  You’ve got to believe you can be an astronaut before you can be an astronaut.  But you’ve got to believe.”

American: The Bill Hicks Story

Bill Hicks was the kind of badass that performed a comedy routine and then ended it with his thoughts on the state of the country and the people in it. Whether they were funny or not. His comedy stays relevant today, even though much of his work was done over 25 years ago, a sign that Hicks’ work is well on the way to legendary status.

American does a great job of telling Hicks’ story, from his childhood all the way to his untimely death. The movie itself employs a really cool technique when delving into his past, where it animates snapshots of Hicks, his family and his friends, creating what looks like a moving paper diorama. It’s always nice when the project about an artist is a work of art itself.


Forgive the mullet. It’s not his fault his heyday was in the 80’s.

The Comedians of Comedy: The Movie

The Comedians of Comedy: The Movie is probably the least documentary-like on the list. It’s more like a tour diary or a road movie, not that that’s a detriment. There’s a lot of offstage hijinks between the four comics (Patton Oswalt, Brian Posehn, Maria Bamford, and Zach Galifianakis), and a lot of moments where one or a combination of them is ranting to the camera.

It’s messy and doesn’t have a singular perspective, but there are so many real moments caught on camera that I don’t even care. In fact the moments are so real that plenty of darkness makes its way into the proceedings. That’s why I really dug this one in particular—oftentimes the best comedy comes from places of pain or sadness, and creative people can sometimes be a little crazy.


Plus, Maria Bamford’s awesomeness cannot be contained.


I struggled with including this one. It’s definitely one of my go-tos because it includes testimony and perspective from so many comedy greats on how daunting getting up on that stage can really be. Especially when there’s some yahoo giving you crap from the safety of the audience. It’s real easy to be a jerk, even a funny jerk, when you’re one of the crowd, in the dark, and being spared every eye being focused on you. And every comedian has had to deal with a heckler one time or another.

But I’m not so much a fan of Jamie Kennedy. I think he’s made himself a pretty terrific movie here, and the scenes where he interviews several critics who lambasted his movies are studies in cringe comedy. The problem is, I tend to agree with the critics. Nonetheless, see this movie if you’ve ever wanted a taste of what it feels like to be in a comedian’s shoes.


Also, everyone is in this movie. You’re probably in this movie.

Notice how 4 out of 5 of these have a title and a subtitle? What’s up with that? I’m hoping mine will be When Life Gives You Clemens, Make Clemenade: The Sara Clemens Story. Leave the titles of your documentaries in the comments. Maybe I’ll put the best ones in the short doc I’m making—I Choose You: The Unreality Story.

Similar Posts


  1. The Comedians of Comedy is still one of my favorite things to watch. Usually when they are doing yet another “Kings of Comedy” or “Rednecks of Comedy” on Comedy Central. It’s the same reason why I watched Dave Atell’s Insomniac, it just seemed more genuine as well as a slight mockery.

  2. i still like the aristocrats, the etomology of a secret comedians joke is such a cool concept. Also all the comedians doing there versions of the joke are rediculous.

  3. Straenge, genuine but slightly mocking is apt for CoC. That movie makes Zach Galifianakis look like a tortured genius but I can’t tell how much of it is real. DoctorG: I love Louie like gangbusters. It’s not a documentary though, despite how hilariously and heartbreakingly realistic it is. And Ness, I totally agree. I figured Aristocrats would be too obvious. Also, I saw all these for the first time within the past year, so they were fresher in my mind.

  4. A great one that i recommend all the time was “When Standups Stood Out”. It documents the Boston comedy scene of the early ’80s, when Denis Leary, Steven Wright, Lenny Clarke, Bobcat Goldwaith and others were coming up. There were something like 7 comedy clubs on one block and the world started noticing them. Really interesting look at what happens when some people make it and some don’t.

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.