Demetri Martin is getting his second act. So far he's mostly been known for his stand-up comedy (like his short-lived, sketch-mixed TV series, Important Things With Demetri Martin), but at Tribeca Film Festival this past weekend, the 42-year-old funnyman proved there's a bit of Hal Ashby (Harold and Maude) in him. On Saturday evening, Martin premiered his directorial debut, Dean, which he also wrote and stars in. I think it's safe to say most in attendance agreed: It exceeds expectations.

The premise is familiar—almost too familiar. Martin stars as the titular Dean, a man who just broke up with his fiancée and decides to spontaneously go to L.A., where he meets and falls for a girl (played by Gillian Jacobs). But don't let the conventional synopsis stop from winning you over. Dean is surprisingly charming and original, with a cast that includes 2016's It Girl Gillian Jacobs (who got on more people's radar after Judd Apatow's Love) and Oscar winner Kevin Kline, who plays Martin's father, a widower struggling to jump back into the world of dating. Dean mixes animation (done by Demetri Martin himself), personal history (the film is dedicated to his father, who passed away 20 years ago), and laugh-out-loud funny jokes people already familiar with Martin's comedy will be pleased to find. Following the film's premiere at Tribeca, we sat down with Gillian Jacobs and Demetri Martin to talk about their favorite jokes in the film, terrible pick-up methods, and why improv troupes kind of feel like cults.

It must be so different sitting there and watching people react to a movie you made. Your directorial debut, too!
Demetri Martin: It’s [actually] like doing a stand-up show. In stand-up you can kind of tell when you’re in trouble. So it was the same kind of thing, like, "I hope they laugh at this." I think it was the shot of Kevin Kline’s jeans early on and when they laughed at that, I was like, "This will be a good night." From then on, I could just enjoy the movie.

There were so many little jokes I enjoyed. What was your favorite Easter egg?
Demetri:
Oh, that’s a good question. There's a shot of Rory Scovel, who plays Eric, when we’re in his room with all of his cat stuff. I was getting B-roll, just trying to get his cat and stuff. Rory just looked into the lens. That’s one of my favorite laughs in the movie and I don’t understand why it’s funny.

Gillian Jacobs: I love it. He's looking beatifically at the camera, just blissed out with his cat in the room. It's so good.

My friend is a single guy with a cat condo in his apartment, so this made me think of him. Gillian, last night you were talking about how you like your character because she is a speaking character with a job and a back story...
Gillian:
Yes! Yeah! A low bar, but yeah. Demetri wanted my character Nicky to be more than just the object of his desire. I really love the fact that she was also kind of stuck in her life.

Demetri: Yeah, my wife helped me. I remember a girl I dated in high school—this is a lesson I learned back then. It’s sad that men have to learn the lesson. She’s a doctor now and she was like, “I don’t know if you ever notice but when you guys get answers right in class you’re brilliant, but I’m a hard worker,” and it’s just that insidious sexism of “You’re a hard worker, sweetie. You can’t be a genius.” Now you get to storytelling and I want to be respectful. Like I’m new, I’m still trying to learn how to do this. I was still in trope land. My wife helped. It’s still humbling to try to be like, how do you tell a woman’s story? 

Gillian: We had the next draft of the script and it was developed even further. It was really refreshing, and actually another friend of mine met to talk about Nicky and said the same thing. Demetri actually cares about three-dimensional female characters.

Speaking of dating and stuff, some of the funniest scenes are ones where you and Eric are negging women and failing miserably. Have you ever actually attempted negging or has it ever been attempted to you?
Demetri:
Oh I’m sure Gillian's been negged...

Gillian: I’m sure, yes.

Demetri: Especially when you add the fame thing. They’re like, "I know who you are... No, I don’t know who you are."

Gillian: Now that you say that, I can think of some instances where I felt someone knew who I was but was trying to be like “And who are you?” And then a mutual friend will be like, “Oh, they’ve watched every episode of Community.” Like, they clearly know who you are. There’s also the status thing in L.A. of constantly being put in your place. Like at this party I’m at this level of fame, but at this party I’m lower.

Demetri: I never felt that in New York.

Gillian: Yeah, it’s such a real thing in L.A.

Demetri: I’m trying to remember when I was still single, but I don’t think I did that.

Gillian: That’s not your style.

You have hilarious scenes with improv actors, but they're also despicable. I gotta know, what's your beef with improv troupes?
Demetri:
Oh, that’s funny. I don't think I have any beef. The thing is, I started doing stand-up in ‘97. The first UCB Theatre opened around that time, so I met a lot of improv people and have spent a lot of time in that world, but have never done it. So I’ve done stand-up on that UCB stage. If there’s any beef I have with it, it's where it veers into cult territory. If there’s any part of comedy that might be a little cultish—and you know it pretty well having done Mike [Birbiglia]’s movie.

Right, Gillian, your other new movie (Don't Think Twice) is about an improv troupe.
Gillian:
 I shot Demetri’s movie way before I shot Mike’s movie, but to have them both at the same festival is funny to me. And I similarly am not from improv or stand-up, so I felt like I was having to do this crash course in improv to do Mike’s movie. 

Demetri: What I can say is that in stand-up, when you die on stage, you die alone. You hear glass or you hear silence. You failed, there’s no question. But with improv—and god bless people because we’re all just trying—the group can come off stage together. So I think that lends to the cultishness. The other thing I was making fun of—whether it’s stand-up or improv—is that these are the worst people to be around because they’re just on all the time.

Gillian: That was very true to my experience of moving to L.A. Because I didn’t come from comedy, I didn’t understand that's how people talked to each other. They do bits. If you go in trying to have a sincere, honest conversation, you’re running into a brick wall sometimes. And I thought people were making fun of me at first, but that's just how they communicate. You immediately establish a bit with someone and then you just continue that for the rest of the party.

Demetri: That’s a good way to put it. In the scene I'm like, “Whoa, I’m not doing bits with you guys.”

Dean is playing at the Tribeca Film Festival 2016—for more coverage of TFF, click here.