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Simon Rich on Man Seeking Woman, Saturday Night Live, and Lorne Michaels

Photo: Jeremy Sutton-Hibbert/Getty Images

For his entire impressive career, Simon Rich has been a person people can’t talk about without running through his origin story: The son of a famous writer (New York contributor Frank Rich) who, after running the Harvard Lampoon in college, graduated with a two-book deal and a job at Saturday Night Live. He has released two novels and four humor collections, worked at Saturday Night Live for four seasons, worked at Pixar, and, most recently, created a show for FXX based on one of those collections, The Last Girlfriend on Earth. That show, Man Seeking Woman, is a deeply weird sitcom-sketch hybrid about the dating life of a young man (Jay Baruchel). Vulture spoke with Rich about the show (which premieres tonight), Saturday Night Live, Lorne Michaels, and his New Yorker piece that unexpectedly went viral.

Why make this show now?
I’ve always wanted to do a show like this one that combines narrative-sitcom storytelling with the absurdity of my favorite sketch shows. I don’t think this is a show we would have been allowed to make necessarily anywhere about five to ten years ago, and it’s just thrilling that FX is taking a chance on something as weird as this one.

Unlike the book, the show has a single protagonist. When you watch it, do you see Josh and see yourself?
The show is really autobiographical, not just for me but for all of our writers, directors, and cast members. The way every scene and every episode starts is with us talking about the humiliating and traumatic moments of our 20s.

Do you think of yourself as a romantic, or do you feel that your opinion about romanticism has changed?
Yeah, like a lot of people, I was pretty cynical when I was young, and that’s reflected by my first few books. When I look back, I’m pretty shocked by how nihilistic and nasty some of the stuff in them is. I got older and hopefully matured a little bit, and I started writing from a little more earnest and honest place. I started writing Last Girlfriend on Earth around the same time I wrote What in God’s Name, which is pretty much a straight-ahead romantic comedy. So yeah, my writing has definitely gotten a little more earnest, and hopefully, more redemptive. I will say we tried to be as earnest as possible with the show. There is a lot of murder and decapitation and monsters and creatures of all stripes, but my hope is that it’s ultimately relatively light.

Let’s talk about the tone of the show. What’s really interesting is that you have these sketches, but you play them as if they really happened — you don’t say it was a fantasy. Aliens actually visit. How do you decide to go that route?
It’s just being inspired by my favorite sitcoms, a lot of which happen to be animated. On a show like The Simpsons, Homer does actually go to outer space, and on a show like South Park, Kenny really is murdered repeatedly. I always fantasized about doing a live-action sitcom that incorporated the same kind of surrealism and absurdity as my favorite animated sitcoms. I was really inspired by Adventures of Pete and Pete, which I worshipped as a kid, and Chris Elliott’s short-lived show Get a Life, which similarly had a lot of surreal aspects to it and a lot of pretty major story discontinuity as well. Also, movies like Shaun of the Dead or Brain Candy, which took certain risks that you normally only see in animated shows or sketch shows, while still maintaining a narrative. I was really excited because I got to cast Mark McKinney from Kids in the Hall and hire one of my all-time heroes, Ian Maxtone-Graham, who was on The Simpsons for 17 years.

The show is all from the male character’s point of view. What kind of thinking went into how the show portrays women?
Yeah, obviously, the show is called Man Seeking Woman, so it tends to center more, at least initially, on a male perspective of dating. But it shifts pretty dramatically as the season progresses. I don’t want to give too much away, but I think if you watch all ten episodes, you’ll be surprised by how female-centered the show ends up being.

Was it a goal to make sure that that was covered?
Yeah, my writing staff and I were always excited to explore dating from more than just a single point of view. Jay is so much the center of the show at first, but as the season progresses, people will see that we’re not really locked into his perspective, but I don’t want to give too much away. I would ask that people reserve judgment on that front until they’ve seen the first ten episodes.

What is your relationship with Lorne Michaels like now, and how has it changed since you were hired on Saturday Night Live?
I’ve gotten a lot closer to Lorne since I met him, but I promise you, I’m still just as frightened now as I was when I met him, when I was 21. Whenever I get a call from him, I fly into a blind panic, so, in that sense, things haven’t changed at all. But he has been incredibly generous with his time. He’s got a lot of far bigger things to do than help with our weird, experimental cable show. He’s still 100 percent running SNL, which is probably one of the hardest shows to run in the history of television, and he’s still doing it and killing it. The most amazing thing about Lorne is that he really trusts writers, and he really trusts artists. That’s what makes him such an admirable producer, is he allows people to take risks.

Is there a sketch that you’re the most proud of?
My favorite: I wrote a sketch I was really proud of for Tracy Morgan called “Rocket Dog,” where he plays a movie director who directs popular children’s movies about dogs going on adventures, and it becomes clear over the course of the interview that a lot of dogs have died in the making of these films. I wrote that one with Marika Sawyer and John Mulaney, who were my main writing partners at the show. I learned a ton from writing with those guys. We also wrote a game-show sketch I really liked called “What’s that Name?” where people remembered the names of minor celebrities but then struggled when confronted with their doormen or their summer interns.

Are you still not allowed to talk about exactly what you did at Pixar?
I don’t think I am allowed yet, but that will change. Probably in a few months we’ll talk about Pixar.

Recently, when The New Yorker website took down its paywall for a short period of time, your story “Guy Walks Into a Bar” went viral unexpectedly. Were you aware that happened? Was it exciting?
It was thrilling! When you’re writing, you can never tell which stories are going to catch on like that, and it would probably be a mistake to write with that as your goal, but I’ve always been completely shocked and gratified and overjoyed with stories that touch a nerve. I’m amazed that one caught on because it’s obviously very strange.

Growing up, you would hear “guy walks into a bar” jokes in locker rooms, and they always had some tough, macho edge to them. They were always about wanting a giant dick or wanting to sleep with women or wanting a blow job. They were always these harsh, masculine, macho jokes, and I never connected to them, even as I was repeating them in locker rooms in Manhattan as a third-grader. I always thought it would be fun to take that famous joke form and infuse it with as much vulnerability and pathos as possible, and turn that trope on its head. So as an experiment, I said, “I’m going to start with the most famous [version] of this classic joke and try to humanize every single character to the best of my ability — emotionally redeem them all.” I almost pulled it off, but I was reading an article about the story, and somebody pointed out that I forgot about the geese. There were geese in the story and I forgot about them, I didn’t get to them, so I feel like at some point, I’ll have to do a second draft of that story where I give the geese some kind of emotional arc as well.

As long I’ve followed your career, you’ve been labeled a wunderkind or a comedy prodigy, but now you’re 30, an age at which people are prepared to see someone be successful. How does it feel to be freed from the labels?
Fortunately, I look 16, so I could probably trick people into thinking I’m a prodigy for at least a few more years. I still can’t grow any facial hair.

Simon Rich on His New Show and His Time at SNL