If there's one thing that sets Demetri Martin apart from his contemporaries, it's that he does jokes. Seriously, very few comedians these days actually ever tell a joke. They relate humorous stories, make funny asides, and even perform sometimes-elaborate slapstick routines, but it's become almost rare for a stand-up set to include a proper joke. But Martin's got a ton of them, usually in the form of drawings that run the gamut from pithy to punny to downright bleak.
So when he decided to write and direct a feature film, naturally Dean came out looking like every other indie-spirited comic's failure-to-launch story that has come down the pike over the last couple decades.

But Dean thinks if he can just avoid all conversations about it, nothing ever has to change. Which also seems to be his approach to his illustrations. But ultimately his desire to do nothing about his dead mother and his childhood home outweighs his desire to do nothing about his career, and he takes a friend up on an offer to go out to Los Angeles for a job interview.
That's where he meets Nicky (Gillian Jacobs), who is young and pretty and fun in a Los Angeles way that's totally fresh to the Brooklyn hipster ennui Dean knows from all his New York friends. They start hanging out and spending time together, with her friend Jill (Ginger Gonzaga) the only fly in the ointment.

What distinguishes Dean from the rest of the pack are the short segments where Martin pauses the literal action to have Dean show us some of his drawings, which of course are Martin's. They're a great window into the way that Dean's mind works. Which of course is also how Martin's mind works, which is why they're such a good comedy bit in the first place.
The drawings are original and quirky and funny, and they're what makes Martin such a good comedian. I get the desire to stretch himself, but outside of his native comedic language Martin comes off as derivative and boring, which he is most definitely not. Maybe there is a way to fit his drawings into a larger comedic narrative, but he hasn't found it yet.
Rating: 2 out of 5