Glory Days: Simon Rich Talks SNL, Broadway, and the Genius of John Mulaney

Simon Rich is a busy man. The former Saturday Night Live writer just released a new book, his first-ever Broadway play opens in December, and he’s hinting that he could be (temporarily) re-joining the SNL writers’ room when his longtime collaborator John Mulaney hosts the show on November 2.

Since 2007, Rich has been regularly releasing collections of short stories, which means that he started doing so the same year that he both graduated from Harvard University and started writing for Saturday Night Live.

He stepped away from SNL in 2011, after spending four seasons making his mark as a master of the “10 to 1” sketch with a little help from regular collaborators Marika Sawyer and John Mulaney. But in addition to continuing his work as an author, Rich has also continued as a small-screen scribe, creating the FXX series Man Seeking Woman and TBS’s Miracle Workers—both of which were based on his own writings. 

At the moment, however, Rich’s predominant focus is on the forthcoming Broadway play based on his work, All In: Comedy About Love, which opens at The Hudson Theatre on  December 11 with an all-star cast. Yes, we know people throw around the words “all-star cast” quite a lot, but this is definitely a reasonable use of the phrase.

For the first five weeks, the show will be headlined by the aforementioned Mulaney, who’ll be starring alongside Fred Armisen, Renée Elise Goldsberry (December 11-30), Richard Kind (December 11-January 12), and Chloe Fineman (January 2-12). For the final five weeks (January 14-February 16), Lin-Manuel Miranda takes over as headliner, along with Andrew Rannells (January 14-26), Aidy Bryant and Sam Richardson (January 14-February 2), Jimmy Fallon (January 28-February 2), David Cross (February 4-9), Tim Meadows (February 4-16), and Hank Azaria (February 11-16).

In the wake of the release of his seventh short story collection, Glory Days, and in advance of the opening of All In, Rich was kind enough to hop onto a Zoom call with LateNighter, wherein he discussed his writing career—both short stories and television—and how his upcoming play came about. He also wasn’t afraid to tease a likely SNL return when Mulaney returns to host on November 2

The following interview has been edited for length and clarity.

LateNighter: After reading Glory Days, I think my favorite story is probably “Mario,” written from the point of view of the Nintendo video game character. I was fascinated by how long that story went on… and that it kept being funny, predominantly just by virtue of adding “-a” after every few words, i.e. “I’m-a Mario!” 

Simon Rich: Yeah, that vowel does a lot of heavy lifting for me in that story. [Laughs] That was an absolute thrill to write that story. That’s the oldest story in the book, the first one that I wrote for the collection.

You’ve obviously compiled quite a few collections of short stories at this point. Do you just keep a journal of ideas where you jot down a phrase or even a single word to remind you of something later?

Yeah, it’s a Word document on my computer. It’s just called “Hooks.” It’s, like, 100 pages long. But a lot of the ideas, I find, don’t lend themselves to short stories, so they just kind of sit idly on my computer. And sometimes I’ll have what I think is a strong premise, but I don’t know how to execute it yet. So there are premises that stay in that file for over a decade before I crack the correct point of view.

Do you have a regular writing regimen, or do you just write when an idea strikes you?

No, I write every morning. And a lot of it is just combing through that file and seeing if any of them strike me as worth pursuing. And I’ll just double back again and again and again. Sometimes it’ll take 20 or 30 glances before one of the premises presents an angle for me.

When it comes to compiling the collections, do you try to do it in a thematic fashion, following a certain concept for each book?

Yeah, I try to make them pretty thematically cohesive, but I sometimes fall short, and I’ll end up putting in a couple of stories that don’t quite fit the theme. But I’ve been a little bit more rigorous about it with my last few collections. I think Glory Days is pretty thematically consistent. Some might say repetitive. [Laughs] But I would use the word “consistent.”

So given that this is LateNighter, you had to know that your time as a Saturday Night Live writer would be broached, but I’m not quite sure about how the timeline plays out: You were still at Harvard in 2007, and your book Ant Farm: And Other Desperate Situations also came out in 2007, but… did you also start at SNL in 2007? 

Yes!

That was quite a year.

Yeah, it was a really exciting year. I learned so much at SNL, and Colin [Jost]… I think my first year at SNL was his third year. And, of course, I knew him from The Lampoon. And I also started the same week, I believe, as Rob Klein. And Kent Sublette, who’s still one of the head writers. So he’s been there this entire time. I think he he started the same day as I did.

Colin and Sublette are so good at writing for that show. They’re both just extremely versatile sketch writers. In addition to being hilarious, they can do so many different kinds of sketches. When I was there, I really only did one kind of sketch, and it was the kind that appeared at 12:52 a.m.

I’ve always been a fan of the so-called “10 to 1” sketches.

Yes, “10 to 1” for most people. For my sketches, they’d push it to more like “8,” “7,” or “6 to 1.”

You obviously started at SNL straight out of the gate after leaving Harvard, but was that something you’d always had your eye on? Or was it something that, by virtue of being at The Harvard Lampoon, you started leaning that way?

Well, as weird as it is to say, I always really wanted to write short story collections. [Laughs] And when I started out professionally, I was mainly writing for magazines. So my first book, Ant Farm, is a collection of stories, some of which I sold to magazines by that point. So in college, I was really trying to be a magazine writer. I wasn’t writing spec scripts or film scripts or plays. I was really focused on trying to write prose. But what happened is, Colin Jost gave a copy of my first book, Ant Farm, to Seth Meyers, who read it, and that’s sort of how I had the opportunity to apply for the show. 

I was extremely excited to start, because I grew up loving SNL. A lot of my biggest influences were sketch shows from the ’90s. I’d obviously put SNL in that category of big influences, but just as big… Well, probably the biggest influence on my writing was another Lorne Michaels-produced show, The Kids in the Hall. And also Mr. Show with Bob and David and The State. SNL was a huge influence, too, but I’d say I was most influenced by Kids in the Hall

I’m presuming you still remember the first sketch you got on air for SNL.

Yes, I remember my first few weeks pretty vividly. My first week, I wrote something for LeBron James that was cut for time. It was a sketch where Bill Hader—I wrote it with Bill and Rob Klein—and Amy Poehler played a married couple. They had a memory foam mattress, and Bill’s character was irate because in the morning when he woke up, the memory foam perfectly preserved his shape, but whenever he came home from work, the indentation would have morphed into LeBron James. [Laughs] So he was very mad at the mattress salesperson, and it became extremely apparent moments into the sketch that his wife was flagrantly cheating on him. That got cut for time, but the next week was Seth Rogen, and I wrote his monologue, and that was the first time I got something onto the show.

And that collaboration obviously worked out well, since you eventually wrote the screenplay for his film An American Pickle.

Yeah! And that was the first time we met: at SNL in 2007, when I was writing his monologue.

Who would say was your favorite host during the course of your years there?

There were a lot of great hosts. I’d say that from when I was there from 2007 to 2011, Jon Hamm was one we always looked forward to. He’s just so versatile and a great natural live performer. I always loved writing for Alec Baldwin.

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I’d put Anne Hathaway on there; very versatile and really hilarious. And she can sing. It’s always nice when they can sing. It just adds a whole other tool that you can use. Oh, and Dwayne Johnson! Great SNL host. But there were a lot of fantastic hosts. We got really lucky, I think, during those years.

When you first got there and started writing for the show, what surprised you most about the process?

I think just how meritocratic it was. Because I’d read all the books about SNL, and it’s often portrayed as this really toxic, backstabbing environment. And that’s not what I encountered there at all. Even if you were the head writer and a sketch didn’t play, it would get cut. And if it was your first or second week on the show and you wrote something that played, they would put it in the show. So I was really amazed to see how fair it was compared to the reports I’d read about it. 

I’ve also read that you felt like you really lucked into finding two extremely strong collaborators as well. 

Oh, yeah. So Marika Sawyer started before I did—she was a second-year writer when I got there—and then Mulaney started one year after me. So starting in my second year, which was the 2008-2009 season, me, John, and Marika started writing together every week. And we did that for three years. Working with them was maybe the highlight of my entire career. Truly. I’ve never had more fun writing than I did writing with the two of them every week. 

Usually when someone in a writing group becomes massively successful, the question is, “Were you surprised?” But I feel like no one has been even remotely surprised by how successful John Mulaney has become.

His success is one of the least surprising things I’ve ever seen. [Laughs] It was apparent from the moment I met him that he was the funniest person in the world. It was instantaneous. Like, within the first five to 10 minutes I was speaking to him, I was convinced he was the funniest person on Earth. Truly. And we started writing together the day we met. I couldn’t wait…

The writers get together for a few weeks before the show starts to write the commercial parodies, or at least that’s how we did it in the late ’00s. So I met him on a Tuesday night about a week or two before the season started, and if my memory is correct, I think we were writing together within minutes of meeting.

And are continuing to work together to this day. 

Exactly, yeah! He was so great when we met, and it’s been wild to see him just get better and better.

Are you excited about the impending premiere of All In: Comedy About Love?

I can’t wait for people to see it. If you could tell my 22-year-old self that someday I’d get to write for John on Broadway, it would have absolutely blown his mind.

How did it come about?

The director, Alex Timbers, reached out to me about the prospect of adapting some of my stories into a show. I said it sounded great, but I had no idea what it would look like. And he said that he’d take care of that part. [Laughs]

So I’m feeling really grateful that I get to collaborate with Alex on it, because I was always excited at the prospect of having actors read these stories and perform these stories before a live audience, but I truly had no idea what it should look like visually. And Alex came in with a really strong, original point of view, and he deserves all the credit for the staging of it. I’m excited for people to see what he’s done. 

In addition to working with John, you’re also going to be working with Richard Kind. I reached out to him and told him I was going to be talking to you, and he promptly wrote back, “Great guy, great writer.”

Oh, that’s really sweet. That’s awesome. I’m a huge Richard Kind fan. I got to work with him one time before this. I cast him as God on my show Man Seeking Woman. [Laughs] And it was just a dream come true to get to write for him. He’s one of the funniest actors in history. 

If Richard doesn’t end up hosting Saturday Night Live sometime soon, I’m going to be very disappointed, given his connections with the show’s alumni

He’d be so great hosting that show. He really would be. And he can sing, too! He’s so versatile and so phenomenal in everything. I can’t wait for people to see him in All In.

I remember in Man Seeking Woman, when we found out he was free to play that part, the writers’ room was just absolutely psyched. I think everybody cheered. They were so excited at the prospect of getting to write for him. 

To bring it back to SNL before we wrap up, what’s your favorite sketch that you ever got on the air?

I think the best sketch that we did—me, Marika, and Mulaney—is probably “Rocket Dog.” That’s my favorite. I don’t know if you can find it online. I hope so! But maybe it’s better if you can’t. Because of how many dogs die in the sketch. [Laughs]

Writing that with Marika and Mulaney was absolutely thrilling. We didn’t think it would ever air, just because of the sheer number of dogs that die in it, but miraculously it made it onto the show. We were perhaps irrationally very proud of that sketch. 

[While it’s not on YouTube, we were able to find “Rocket Dog” on Vimeo. You’re welcome. – Ed.]

Lastly, do you have a favorite sketch that didn’t make it to air?

Well, luckily, we’ve gotten most of them on now. Because every time John hosts, he sort of forces the issue and gets our favorite sketches over the finish line.

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A lot of the sketches that we’ve had on the show since 2011 have been sketches that we wrote with Marika when we were writers, like “Toilet Death Ejector” and “Switcheroo.” Those are sketches that we wrote 15 years ago, and we couldn’t get them to air them until Mulaney became enormously famous. [Laughs]

Of course, he’s already on the schedule to return as host for this 50th season. Do you anticipate that there’s something else from the archives that’ll make it on the show?

I really hope so. We’ve got a big pile of failed sketches, and I’m excited to go through them all. Hopefully we’ll find a winner. And if not, we’ll try to write something new!

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