Don’t know about you, but I first “met” the man pictured above through Important Things with Demetri Martin, his short-lived Comedy Central series that blew me away about seven years ago. For those who enjoy modern Stephen Wright-like observations mixed with goofy music and irreverent artwork, the man is a whimsical godsend… from New Jersey!

Just check out this clip from the second season of the show, in which he demonstrates the way adding simple lines can completely change the meaning of a drawing, and you’ll see what I mean.

Since that time, I’ve kept tabs on Martin’s career, checking out his comedy specials and albums and semi-obscure movies like Lake Bell’s charming In a Worldand generally loving them. So naturally I was stoked to hear about Dean, the new tragicomedy that he wrote, directed and stars in alongside Kevin Kline, Gillian Jacobs and Mary Steenburgen.

It’s a coming-of-age tale about a guy dealing (badly) with his mother’s death (not a spoiler, it’s in the trailer), so it’s got more pathos than most of his material, but there are still plenty of laughs. And because of his character’s career (he’s an illustrator), it’s a great showcase for his silly yet cerebral artwork as well. Critics seem to like it, too: It was named Best Narrative Feature at the prestigious Tribeca Film Festival.

So, with Dean opening in select cities later this week, we caught up with this multi-talented fellow to ask about the movie and the mindset behind some of our favorite Demetri drawings. We came away with a deeper understanding of the man, his talents and life itself. No joke.

“If you put your head down it immediately looks like you’re grieving, but you may just be checking glow-in-the-dark stuff.”

You’re probably getting this question a lot, but how autobiographical would you say Dean is?
Emotionally it’s very autobiographical, but it’s all fiction. I don’t think there’s anything in there that’s really happened to me, but in real life my dad passed away. His name was Dean. That’s why I named the movie Dean. It was kind of an homage to my dad, and this was 20 years ago, and my dad was young. He was 46 when he died, and I was 20. That’s not something I’ve talked about on stage, and I don’t put that in my comedy. I usually just focus on jokes or whatever, but here I thought there was something worth talking about in film format.

The music is sort of a character in the film, and you’re obviously a musician yourself. I’m kind of curious what the story is behind it…
I had this album called Pete Dello and Friends. I got the CD years ago, and I like almost every song on that album. And when it came time to edit the movie, I had this fantasy. I’m a fan of Hal Ashby’s and I like movies like Harold and Maude and Shampoo and Coming Home. And specifically in Harold and Maude, Cat Stevens was almost like a character, his voice. That music had so much to do with the identity of that film [and] my experience of it. And I had this little fantasy that I could do something like that even though I’m not Hal Ashby [and] my film is nothing like Harold and Maude. I like that idea of the relationship between the music and the storytelling, and then something clicked in my head and I thought, you know, these Pete Dello songs are so beautiful and there’s something about the timbre of this voice, his sincerity.

When I put it against some of the stuff that I shot, something nice happened with the material, and I had no guarantee that I’d be able to get the songs in the movie, but luckily I reached out, I got in touch with him. I found his information online, I emailed him, then I started this process and it did work out where I could get those songs, and that’s one of my favorite things about the movie, because I think the music is great and it holds up well. I mean, it’s from 1970 or ’71.

“You know, you have this plan and you want it to go a certain way, and it’s so hard to remember that success is so not linear. I mean, what is in life?”

Gillian Jacobs is just so fucking delightful in everything she does. Is that how she actually is or is she secretly a real B?
She’s really interesting, because being on the other side of this stuff now, where I’m the filmmaker and I’m casting people, and even as a writer trying to write parts for people, you can see the epidemic, especially in comedy, of the white dude who thinks he’s funny, and they’re going to make his story and put everyone around him to laugh. And how the women, they get just kind of shoved into these parts where they have to look pretty and smile for the guy and everything.

And in a way, I pictured the part of Nicky being… it’s just a little bit different. Something I’ve learned about casting, when you get a real human being they’re going to change your writing. She added a different dimension that I didn’t expect. I almost stereotypically wanted to have some woman character validating my character, like, oh, he’s funny and that’s why I like him and all this, but she brought something really different to it. It wasn’t like she was just laughing at all my jokes, and I think it made it a lot more real, and it was kind of modern, you know. I thought it was pretty cool.

So I want to do something a little conceptual here. This may backfire horribly, but for a long time I have enjoyed your drawings, and of course you carry this talent into the film with your character being an artist. So, I have some of your drawings and I’m looking for sort of a director’s commentary on them…
Yeah, sure. That’ll be cool.

First off, we have the hot coffee, the loud coffee, the coming at you coffee and then the hot, loud, coming at you coffee.
So I did standup, right? I did my first special and it was called Demetri Martin. Person. and I put some drawings in it, and there were simple animations, and I played piano a little bit. Comedy Central liked my special and they said, if you could do something like your special, we’d be interested in shooting a pilot for a series.

So we did this thing on the show where I had a screen in the wall and it was like a drawing that could build. It was different than just having it on paper. And that coffee drawing was one that I came up with where I was like, it would be cool to take a simple object and then just add different lines to it, so that it’s the same drawing but it gets slightly changed without it being like a cartoon or something. And that led to that one.

Screen Shot 2017-05-30 at 2.17.19 PMNow we have “grief-stricken” and a man with his head in his hands, and then “trying out glow-in-the-dark item.”
Oh yeah, I still do that. I don’t know if it’s my generation or something, but when I was a kid glow-in-the-dark stuff was such a cool innovation. And you could buy this stuff, but you’d always have to test it and you’d either go in the closet or like put it in a bag or something. And even as an adult I was looking at watches and I wanted to know if you could see the numbers and stuff, the hands in the dark, because some watches glow in the dark, and I think that led to that drawing. But yeah, if you put your head down it immediately looks like you’re grieving, but you may just be checking glow-in-the-dark stuff.

Now this one kind of speaks to what you were just saying about Gillian Jacobs, but it’s a man and a woman, and the man has a thought bubble of the woman thinking about him…
Thinking of him and she’s just thinking of herself. Yeah, I like that. I’m married now and I’m pretty set, hopefully my marriage is going to last and everything’s OK, but now that I’m not single and I’m not out there, I just think about dating and being a dude who’s trying to meet this person and everything.

You know, it’s so easy to just think from your own perspective and just the whole mansplaining and you know what I mean? You’re so busy worrying about trying to impress the girl or get a girl to like you, you get so wrapped up in yourself and it’s just funny. You’re right, it does kind of resonate, it is kind of similar to what I did with Gillian’s character in the movie, where it’s like, well wait, she’s got her own story too. Like he thinks it’s all about him but we’re all just trying to get through it. So, I like that drawing. I think that one’s pretty economical.

Alright, now we have the skull and crossbones (when he was still alive).
That’s one of my favorites from way back and that was in my first special. It’s still funny to me that the human skeleton is so scary, you know? That a skull is just such a scary thing to see but it’s just part of our makeup. So, I thought yeah, well, what did that guy look like when he was alive? And I made him look kind of like, I don’t know, maybe an accountant or a math teacher or something.

SuccessNow this is the last one and a nice button on where you are, because you have done so many different things, but you’ve got these two side-by-side drawings, “success, what people think it looks like” and then “success, what it really looks like…”
You really have picked up on my favorites, because I love drawing and I have a new book, it’s going to come out in the fall, a big batch of them, a couple hundred new ones, but that one was in my very first book. That was not a book of drawings per se, it was like comedy essays, but then I put some in there, and I really like that one because to me that is, just being a little bit older now, what my life feels like.

You know, you have this plan and you want it to go a certain way, and it’s so hard to remember that success is so not linear. I mean, what is in life? And people have said they like that drawing, because it just goes all over the place. You’re going backwards, you’re going down and then if you stick with it, hopefully you end up more or less in the direction you thought you were going to go. What a surprising winding route it is.