Mike O’Brien and Man Seeking Woman Are Perfect for Each Other

Like many great episodes of Man Seeking Woman, last night’s “Ranch” strikes a delicate balance between sketch comedy and half-hour narrative storytelling. Like a sketch, it takes a simple joke to a ludicrous climax: Josh’s mother is over-attached, first insisting they spend too much time together, later attempting an assassination to gain his attention, ultimately driving her husband to take her out to the shed so he can end her suffering. Like a full sitcom story, it drags Josh through a structured narrative ringer until he learns his lesson: Initially disdainful, he ultimately makes time for his mother while insisting on boundaries.

All along the way are juicy comic flourishes. In one scene, Josh’s sister, as an archaeologist of sorts, briefs his girlfriend Lucy on their parents’ peculiar customs and how she ought to behave when they meet. Later, Josh’s father, clad in a straw hat and overalls, wielding a shotgun, ponders taking his wife to the scented candle aisle at Target (“Tarjé”) and euthanizing her. In other words, the show’s world is at once dense as Portlandia’s Portland and spacious enough to allow for the sort of emotional growth you’d expect from Master of None.

“Ranch” was written by Mike O’Brien, the former Saturday Night Live writer and short filmmaker. Man Seeking Woman is a natural home for his talents. As surreal and expressionistic as it gets, its characters are always grounded in emotional reality, facing alien overlords and grunting trolls with the same straight-faced credulity you’d give a telemarketer calling after hours. The same can be said for O’Brien’s in his impressive sketch comedy oeuvre, from his marvelous Jay Z biopic to his web series 7 Minutes in Heaven. The joke is usually less what’s happening than how seriously he reacts to it.

Paste caught up with O’Brien this week to discuss “Ranch,” how Man Seeking Woman keeps things fresh, and jokes that don’t make the cut.

Paste: So your episode this week is a pretty good example of how Man Seeking Woman steers between sketch and narrative comedy sensibilities. Can you talk a bit about treading that line, both yourself and the room as a whole?

Mike O’Brien: I was only onboard for this season, so I think this method has kind of evolved over the three seasons. But the way Season Three would work is we would pretty much try to get the story down first, without what we called “the premises”—the sketches that are woven in. We would try to get the stories first, with index cards on the corkboard. And then we would start saying, well, what’s an exaggerated version of that? How do we make a sketch out of that story beat? And separate some of them that way. There were other times where we were just randomly like, you know, I’ve got a funny sketch that’s related to dating, meeting the parents—some of these scenarios that are tackled in general. There were perfect sketches, but if they didn’t get connected to a story that made sense, unfortunately some of those never see the light of day. Because they had to be connected, they had to go in order.

Paste: Is there any sort of bible or rulebook for how this world works?

O’Brien: Not a literal one, but it’s all in Simon’s mind. It would often come up, for instance, that no one can magically have a new outfit on. You can’t, like, cut to someone in a suit and tie, cutaway, come back and they’re in a knight in shining armor outfit. You’d have to give them time to change. There’s funny rules like that, that we’d run into, which was always sort of weird—you could say, like, “Yeah, cats are about to fly, but we’re worried about the logic of this other part?” But it still has some sort of consistently with it. Or else it could feel really unsettling to the viewer. You need some rules.

The other thing to notice is that there will often end up being a door, a literal door to get into the sketch. A lot of times people’s emotions are building in the emotional door, and they’ll say “Come with me through here” and you push open a door and they’re in a magical exaggerated version of the emotion they were in. So doors into the sketch happen a lot in this season.

Paste: A thing I love about the show is how it reinvents itself in big and small ways, and the sort of big reinvention this season is that Josh is, uh, no longer seeking a woman. Can you talk about the discussions that went into breaking the season? How do you guys talk about keeping things fresh?

O’Brien: As soon as we came in, day one, Simon knew that much. He was like, “I definitely want it to be one relationship explored further than we have ever before.” I think the longest one of Josh’s significant others had been around was three, maybe four episodes tops. And all ten [episodes this season] are just him and this one girlfriend. So we knew the first two minutes of the first day. And we were like, okay, let’s brainstorm things we haven’t had previous seasons, because we didn’t get to where you’re moved in, you’re meeting the parents, all the more serious steps. And by the time we were mostly done writing the season, we were starting to do the same for Four—if we’re lucky enough to get a fourth season, we’re already kicking around, what would be another way we could mix this up again?

Paste: I read an interview with Simon from last year where he said the cast was a big part of the brainstorming process. Was that the case this season too?

O’Brien: Yeah, Jay Baruchel came and hung out with us for at least a day and brainstormed. At this point he obviously understands the character of Josh Greenberg so well that he can really say, “I don’t know if that’d be realistic,” or “Hey, what if we did this?” and informed it that way. One of the things he would also say on set that would make us laugh is, “Is this too dumb, even for Josh?” And then on set as well, Jay Baruchel and Katie Findlay and all the supporting characters are really good at improvising as their characters, suggesting other routes to go. Obviously at that point we couldn’t change a whole sketch premise, but they definitely affected how the characters interact in that world a good amount.

Paste: Most people probably know you from SNL and the internet. Is this your first sitcom staff writing job?

O’Brien: It is, yeah.

Paste: How’s it compare to working on SNL? What was the learning curve like?

O’Brien: It was a really satisfying transition into this world, because it does have a sketch element to it. So it was kind of fun to still be trying to think of how to execute and heighten four-minute sketches. But it’s also, after having done that so much at SNL and Second City before that, ten years of writing sketches made me kind of crave, like, “Well, I like when people exist for more than four minutes, sometimes.” Having two main characters exist for ten episodes, and having an emotional arc to all that was also very satisfying. It was like a halfway house of sketch-narrative, which was nice.

Paste: What proportion of outlandish ideas that end up on the cutting room floor? Do you have any particularly memorable bits that didn’t make it into the season?

O’Brien: There were several that were the writers’ room favorites that didn’t make it in. Let me think of one… We all loved this one where the character Mike, played by Eric Andre, who’s very immature in his dating style, tries to become more mature. And it seems like he has for a minute. He’s dating a mid-thirties, very successful—let’s say a banker or something—woman. And they’re at dinner, and she’s very distinguished and serious, and it’s like “Wow, Mike really is better.” Then she starts to act weirder and weirder, she’s throwing little fits, she tries to start a food fight, and you all of a sudden discover he’s dating someone who body-swapped with their bad-girl daughter. And Mike gets sad because he sees that she’s learned a lesson about appreciating how hard it is to be a mom. So he knows their date is doomed, the magic’s gonna end any second.

So the body-swap double date was always killing us. It always felt like it would be a really great performance piece for the actor, but it didn’t vibe with one of the stories we had going on between Mike and Josh, so we didn’t end up doing it.

The other thing is that everyone in the writers’ room, at some point, had a fun detail about their own moms that ended up in the own script. Some didn’t make it into the final edit, but there are specific details that we gave to the Robin Duke character, Patty, that were from a lot of our different moms. That was fun to write—my parents are always describing the Blue Bloods family tree to me, and I was glad I got that in there.

Paste: I loved that joke.

O’Brien: We only got the fake Blue Bloods episode going on in the background, so obviously there’s a lot of Blue Bloods on the cutting room floor. I’ve never seen a Blue Bloods, no one in the room had, and we insisted on not researching or making that accurate. All we knew is it’s a big family with a lot of police officers and they probably talk about that a lot.

Paste: I know you’ve been performing a solo show at UCB for a while, which I narrowly missed last month. Is that working towards a special, or another album?

O’Brien: That kinda is just a fun way to keep messing with material that goes towards all different places. I’ve done one every couple months for maybe twelve years—I’ll do another one in February or something, and then another in the summer. I try to do an hour of solo stuff every two months, and have at least two new things, they end up in lots of different places. It’s very cathartic, and a good way to force myself to be writing all the time.

This interview has been lightly edited and condensed.