Photo: Maya Robinson and Photos by SNL/NBC

With FXX’s Man Seeking Woman returning for its second season last Wednesday, we asked the show’s mastermind Simon Rich to look back on his years as a Saturday Night Live writer and pick the most obscure sketches he penned. He obligingly chose nine, with one caveat: “All of my SNL sketches were obscure, so I went for my favorites.” With constant praise for the cast, the hosts, and his co-writers John Mulaney, Marika Sawyer, Mike O’Brien, Colin Jost, and Heather Anne Campbell, and a ton of self-deprecation reserved for himself, Rich took us through the thought process of creating one-joke premises, making dog death funny, adding in ass humor, and much more. “It’s very important to note that none of these sketches were popular or particularly successful,” he says. “These are sketches I unfortunately loved writing.”

“O.J. Jury Selection,” September 20, 2008

The premise: After O.J. Simpson is arrested for kidnapping and robbery, it’s really hard to find a juror who doesn’t know about him.

During the original O.J. trial, which I was in middle school for, there were jokes about how hard it would be to pick the jury given that it was the trial of the century. When he was arrested again, it got me thinking about which types of people would have somehow not heard about O.J.’s crimes at this point in American history. Colin Jost is one of the funniest writers in the world — before SNL, I got to work with him at the Harvard Lampoon — and I remember coming to him with this idea. We cranked out the sketch pretty quickly. It’s essentially just a list piece.

“Family Flix,” March 14, 2009

The premise: Kristen Wiig interviews Tracy Morgan about his children’s movie Rocket Dog, which featured a disturbing amount of on-set canine fatalities and repeated use of Tom Cochrane’s “Life Is a Highway.”

Most of these sketches I wrote with Marika Sawyer and John Mulaney. They are the funniest writers I’ve ever met in my life. This is embarrassing, but Marika, who is a producer on Man Seeking Woman, Mulaney, and I constantly text each other failed jokes and sketches we wrote years ago. This premise came from one of my all-time heroes, Paula Pell, who is responsible for some of the funniest sketches ever written on SNL. She’s also incredibly sweet and warm, and she loves animals. I don’t remember how it came up, but there was talk of animal abuse in the filming of some movie, and Paula was absolutely horrified — my reaction was to come up with this sketch. Animal cruelty is a very hard sell, so when we were writing, we never imagined it would make it onto the air because so many dogs die in it. Most of the time was spent on deciding which song to play during the murdered dogs’ in-memoriam sequences. When Marika pitched “Life Is a Highway,” we knew we had a chance of getting this one on. Hopefully, it didn’t upset Paula. I don’t think it did, but now I’m scared to ask her. As long as we weren’t actually hurting dogs, she was usually fine with things.

“Fraternity,” December 19, 2009

The premise: During his frat hazing, a pledge (Andy Samberg) realizes that the brothers of Sigma Lambda Omega can’t read.

Some of my all-time favorite sketches have a really a simplistic conceit. This is probably the simplest, some might say stupidest, sketch I ever worked on. It is literally one joke said in increasingly loud voices. Seth Meyers made fun of me for this because it set the record for fastest turn — I just bluntly state the premise like four lines in. I had seen a fraternity hazing ritual at some point where somebody kept saying, “What does this say?” and my mind just naturally went to the premise, which was, “Wouldn’t it be funny if the reason they keep chanting that is not out of macho strength but out of desperate weakness?” It’s something that always made Mike O’Brien and I laugh.

“The New Boyfriend Talk Show,” October 9, 2010

The premise: A kid (Andy Samberg) interviews his mom’s (Jane Lynch) 100th new boyfriend (Jason Sudeikis).

This one is very loosely based on a piece from my first book, My Mom’s All-Time Top Five Greatest Boyfriends, which is a kid writing about how cool all his mom’s boyfriends are, and it becomes clear that she slept with an entire hockey team. It definitely helped that we had some great performances, including Fred Armisen’s disgusting Gene Simmons impression. It was just completely grotesque and hilarious, so we were always trying to sneak it into everything we could.

“Beauty and the Beast,” October 17, 2009

The premise: Belle (Kristen Wiig) realizes that the Beast (Gerard Butler) thinks she’s not really that pretty because she doesn’t have a “big ol’ ass.”

“Most of these sketches would not have aired if it hadn’t been for some bit of creative inventiveness by a talented actor. They elevated a lot of second-rate material, and sometimes even third-rate material, to the point where it could air. I always thought it would be hilarious if it turns out that the Beast thought she was a beast. Then it shifted into ass territory. Mulaney, Marika, and I didn’t have any kind of official motto when we were writing together, but looking back, I would say an unofficial motto might be, “Get to the ass stuff as fast as possible.” It seems to be mainly what our creative goal was those few years.

“Some Big Shot,” May 15, 2010

The premise: An old businessman (Alec Baldwin) tries to help out a hooker (Jenny Slate), with a surprise twist.

Of any sketch I ever worked on, this is the one I’m most shocked that it aired. There is about two or even three minutes without a single attempt at a joke. It’s like three minutes of pure drama, and then a disgusting joke. The read-through played exactly like it played on TV: just bewilderment and confusion. Sometimes at the table, you’ll get pity laughs when a very sweet writer, usually Paula, would chuckle occasionally during a terrible sketch to try to make sure the writer didn’t go and kill themselves. I remember this getting a number of pity laughs because people thought we had lost our minds. Then finally we got to our disgusting payoff.

“George Washington Returns,” February 28, 2011

The premise: George Washington (Russell Brand) returns to the present in a time machine to settle a debate about the Founding Fathers among Nancy Pelosi (Kristen Wiig), John Boehner (Bill Hader), and Rand Paul (Taran Killam).

I wrote this sketch with the extremely talented Heather Campbell. The idea is basically, if George Washington were to come to the future in a time machine, his first thought would be pure terror and panic, and being a trained soldier, he would probably murder everyone in the vicinity with his bare hands. The thrill of this is that political sketches on SNL tend to appear early in the show and have a satirical point of view. We tried our hardest to misdirect, in the first 60 seconds, that this was going to be a very dry, very salient piece of political satire. Then it just turned into what it actually was: a piece of insane slapstick violence. Audiences probably expected that it wasn’t going to be trenchant political commentary when it was coming on at 12:58 a.m. We were very pleased with that one. It just squeaked by dress rehearsal.

“Noodles the Dog,” March 12, 2011

The premise: A couple (Kristen Wiig, Zach Galifianakis) tell their kids about their dog’s death, which was caused by autoerotic asphyxiation.

No video online, but here’s the transcript.

The one prop that I kept from SNL is the porno from this sketch, a dog porno called Puggs. It features a dog with giant humanoid breasts. It’s one of the most physically upsetting props I had ever seen in my life — it’s just a horrific-looking object. I still have that copy of Puggs in my desk. That’s my only SNL prop, and I treasure it. It’s another one of those topics we were always trying to get into sketches any way we could. Ass stuff was usually Plan A, and autoerotic asphyxiation was usually Plan B.

“What’s That Name? Celebrity Edition,” May 21, 2011

The premise: Justin Timberlake and Lady Gaga, playing themselves, face off in a game show where they have to remember people’s names. Timberlake can’t remember a groupie nor ‘N Sync bandmate Chris Kirkpatrick (Taran Killam). Gaga remembers everyone.

This was rare for a sketch of ours because a lot of people actually saw it. The thing I was most excited about with this sketch is that it introduced the character of Vince Blake, who is Bill Hader’s incredibly sleazy, abusive game-show host that he ended up doing a number of times. It’s a really aggressive show, What’s That Name, shaming people for their privilege in front of a huge audience. Timberlake was always game for doing self-deprecating jokes, totally willing to make fun of himself. We knew he would be cool with being bullied by Bill’s character. We felt bad about [Kirkpatrick] because we didn’t want the joke to be on anyone but Timberlake, and that’s why we made sure to have Lady Gaga go crazy with excitement at the sight of him. We just wanted to diss Timberlake again and again as hard as we could — with his cooperation, of course.