In the past three years alone, Michael Showalter has published two books; completed a stand-up tour; launched a podcast; penned episodes of Adult Swim's Childrens Hospital and Newsreaders, and ABC's Super Fun Night; reunited with The State; starred in the web series American Viral; co-wrote the romantic-comedy spoof They Came Together; and somehow still found the time to get married and have twins.

If you're feeling guilty about lounging on the couch this weekend, just wait: Showalter is even busier this year. Yesterday, he unveiled Hello My Name Is Doris, a film starring Sally Field that he directed and co-wrote, at the 2015 SXSW Film Festival. And on July 17, Netflix will release Wet Hot American Summer: First Day at Camp, a follow-up to the 2001 cult film; Showalter is co-writing all eight episodes and reprising the role of Coop. He phoned Esquire from the set of First Day at Camp to discuss his new movie and the upcoming series.

How did you wind up making a movie about a sexagenarian who starts running with twentysomething hipsters?

So I was teaching screenwriting at the [New York University] grad school, which I loved, and I saw a short film at the grad school, not by someone I was teaching, but a student [named] Laura Terruso. It was called Doris and the Intern. The character this movie is based on came from that. At the time, I wasn't like, I want to make this into a movie. I just thought she made a great movie. From there, I became friendly with Laura and we talked about doing something together and we ended up on this, an adaptation of the short. We took the basic seed of it: eccentric, wallflower-ish woman working in an office becomes infatuated with a younger coworker. We created a whole world for her—she's a hoarder, a recluse—and a whole life. We also expanded on the "Emperor's New Clothes" aspect of hipster culture that Doris accidentally fits into.

You directed The Baxter in 2005. Why did you wait so long to try again?

After The Baxter, Michael [Ian] Black and I wrote a movie together [that did not wind up happening]. Then I went and did Michael and Michael Have Issues. Then I got into teaching. Looking back on it now, it does seem like a lot of time went by, but it was sort of like getting my ducks in order about what I really wanted to do. There was teaching, stand-up, TV stuff, directing, meeting the woman who is now my wife, all that stuff. I directed a full season of the MTV show Hey Girl and did a bunch of Internet-y stuff. I did a pilot on IFC based on my web show, The Michael Showalter Showalter. So this Doris thing was a departure from what I was doing. But if you've seen The Baxter, there's a strong comparison to be made between the two stories. The Baxter is a man out of time. Doris is a woman out of time. They both have an antique quality of being invisible, fragile. The world could hurt these people. I connected to the Doris character because she's a new comic protagonist that I had not seen before.

You're known more for your alternative, oddball comedy, but Doris is not that style. Was it difficult shifting from straight comedy to a goofy-slash-somber balancing act?

For me, no. But that was Sally Field's concern, interestingly. She was very skeptical of how we were going to pull off the tone we were aiming for. There's straightforward screwball comedy, misunderstandings, physical comedy, and more of what my "brand" would be. But there's also very, very serious, sad stuff that's about this woman and what her life is. So for me, that was a huge step for myself, creatively. Taking on material that isn't just comedic, which is absolutely what I want to do. It's uncharted territory, but it's where I want to go.

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Sally Field in

I imagine that conveying your comedic sensibilities would be difficult, even to a seasoned actor like Sally Field.

It is difficult. You can't explain that tone. To a Sally Field, you have to say "trust me." She read the script, obviously. I think she was very intrigued, interested in the character, interested in the story. She saw something there that compelled her artistically. As any actor taking on a part as big as that part, there must have been something she found in this character that she could connect to. I could speak to those, but I won't because they're personal. The serious stuff she could wrap her mind around. It was the marrying of serious character stuff to silly comedic stuff that she was less clear about.

Jack Antonoff plays a rock star named Baby Goya. It's so perfect that I assume there was a reference point.

That was the invention of Laura Trouso. We were trying to think of a silly, unbelievably prog-rock, pseudo-intellectual, self-serious name that was also ridiculous. It's Baby Goya and the Nuclear Winters. It's wonderfully absurd. And Jack Antonoff is someone I knew but didn't know well. I was a huge fan. I asked, and he did it. He wanted to be silly.

Speaking of music, Hello My Name Is Doris receives a thousand bonus points for including Pearl and the Beard tracks, a band everyone who loves greatness should know about.

They're so good. Other bands that I love that I might compare them to, which I'll explain, are Crosby Stills Nash & Young and The Band. These are other bands where all the members sing and write songs ... Pearl and the Beard all three individually unique people, and together they create this thing. They have so many flavors and shades. There's punk, folk, rock, blues, gospel—everything. They're a perfect fit. They capture the cluttered, controlled chaos of Doris. It's [also] how I see New York City, this clashing thing that somehow works. Doris goes through all these worlds in the movie. She turns a corner and goes into a world. That's what New York is like. She's in Staten Island, at a Baby Goya concert, a folk cafe—all these universes. That's my New York: an endless maze of worlds.

That's why I loved Stella. It's specifically "New York absurd."

There's a hoarding episode in Stella, where they booby trap their house and become recluses. They put blankets on the windows. They're Howard Hugheses. Hoarding, cats and becoming a recluse are things I feel very connected to.

In the wings, you have the Wet Hot American Summer follow-up for Netflix. Based on occasional rumors over the years, the idea was brewing for a long time.

It is one of those things we'd have conversations about. It was this or that; it didn't quite feel right. But in the last three or four years, the conversations picked up. [The Wet Hot cast] had a ten-year-anniversary article and we did a couple of events, one at the San Francisco sketch fest, then one in New York. In the wake of the ten-year anniversary, the conversations ratcheted up. We started working on a feature, but that dovetailed into the emergence of Netflix and a feeling of, in any sort of blue moon, this could be a perfect fit.

Was it easy to adapt an idea conceived as a feature into a series?

I think Wet Hot lends itself to a TV format. It's episodic. We've evolved it past a sketch thing, but I do think it works in a short, serialized form, almost like a comic book. It didn't feel like we had to reinvent the wheel to make it work.

And the opportunity was finally there.

It wasn't an overnight thing by any stretch. It's been brewing for five years and really ramped up around the time of our ten-year anniversary. So we said, "Let's do this." And the absurdity of us being in our forties... We really are generationally different than when we made that movie and it just felt like the time was right.

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