At the height of MTV’s grip on ’90s youth culture, David Wain and his friends from New York University created The State, an MTV sketch-comedy show that, despite its short run, developed a vehement following and ignited the comedy careers of Wain and the group’s ten other members, including Michael Showalter, Michael Ian Black, and Thomas Lennon.

In the twenty-two years since The State’s inception, Wain has oscillated between mediums—performing stand-up with the comedy trio Stella, writing screenplays, directing features, and acting, almost always in the role of the “aw, shucks” ham. Wain consistently distinguishes himself from his comedic contemporaries by eschewing the standard cynicism and examining the absurdity of social rituals, small talk, and the general silliness of history.

Recently, Wain has written, directed, and starred in thirty-two episodes of Wainy Days, a web series in which he plays a bumbling, hopeless romantic who falls in and tragically out of love with one fetching actress after another, all within the span of a five-minute episode. Wain also serves as writer, director, and producer of Adult Swim’s Childrens Hospital, a sort of darkly comedic version of Grey’s Anatomy in which sociopathic doctors feign morals and good intentions to ruin the healthy lives of their kid patients.

Wain continued to work with members of The State on films such as The Ten, Role Models, and the classic camp parody Wet Hot American Summer, all of which were cowritten and include appearances by various State members. At the time of this interview, Wain was editing the film Wanderlust, written with Ken Marino and produced by Judd Apatow along with Wain, Marino and Paul Rudd.

I spoke to Wain a few days before Christmas about the challenges of switching artistic formats, comedy spawned from happiness rather than pain, and whether or not comedic directors lose their fastball with age. Wain lives in New York with his wife and occasional costar, Zandy Hartig. This interview took place in L.A. over dinner.

—Toph Eggers

I. PUBLIC THERAPY

THE BELIEVER: Can you talk about the process of screenwriting with a partner? Who starts it off? Whose idea do you begin with? How do you trade it back and forth?

DAVID WAIN: Well, in this case, Ken [Marino] and I did our movie The Ten together, and he also wrote Role Models with me. We also wrote a lot of other screenplays for hire in between those projects. But in the case of the two movies that we’ve sort of made that are our own movies, which were...