By the time the stand-up behind one of Vulture 2016’s list of best stand-up specials and the co-host of The Jackie & Laurie Show podcast, Laurie Kilmartin, hit the Conan stage to perform stand-up last year, she was ready. Sure, she’s performed on late night, and Conan specifically, plenty of times in her 30-year career, and in general she is one of the most dogged joke crafters working, likely to run a set like this hundreds of times before bringing it to TV, but beyond that Kilmartin has had her jokes heard by Conan audiences most nights over the last decade. Kilmartin has been a monologue writer for Conan O’Brien since 2010, submitting dozens of jokes a day, with the hopes of getting two or three on air.
This set and the monologue jokes she wrote during the day are the subject of this week’s episode of Good One, Vulture Comedy’s podcast about jokes and the people who tell them. Listen to the episode and read a short excerpt of the discussion below. Tune in to Good One every Monday on Apple Podcasts, Spotify, or wherever you get your podcasts.
On your podcast you had Jackie [Kashian] record you the moment before the set or before the show started. And you were listening to Conan do the monologue. What were you listening for?
I just wanted to know if they were a good crowd. I wanted to know if the laugh was long or short, and I wanted to see if Conan had to work. I can tell when he has to work with an audience and pump them up or if he gets to sail with them a little bit. And they seemed really, really good. I was relieved. That doesn’t mean they’re gonna be good for the comic, but it’s a good sign.
Also you seemed to want to know if monologue jokes you wrote go on.
Yeah, I left the room maybe like an hour early for makeup, but I had stuff in when I left. Up to the very last second he can take jokes out. There was maybe one or two at least. I was happy.
How is writing a monologue joke different than stand-up for you?
I’m not political onstage. It doesn’t interest me. I can see it dividing the room, and I don’t want that. I wanna write dark jokes that everyone laughs at, or most people laugh at. I guess I just wanna aggressively document my life on this earth. I don’t know how that divvies up, but I do know I got a lot better at the craft part of joke writing when I started at Conan. You just have to do so many every single day. The feeling of, I have nothing left, but I have to write ten more jokes. Well, I’ll find something — it kind of helps me work on jokes in my act, as well. But they feel very separate.
How do you write a monologue joke?
At first you get your host’s voice in your head, and you just have a separate track in your brain of things you know he likes. Some jokes come really quickly and they’re good, and some are a labor and they’re awful. Sometimes the awful ones get picked because they work. In the morning, I feel really good because the news stories are all fresh. The hardest thing is by 2 in the afternoon the news cycle hasn’t changed that much and you’ve read every story. It’s like, All right, let me go back to this idea that I already tried to write jokes for three times already today. Let me see if I can find another angle. That gets really tough.
A few months back you tweeted something.
To the dismay of some people, I might add.
Sure, but to the, whatever the opposite of dismay is, to other people. Stephen Colbert was like, “This is incredibly useful.”
I was like, “Oh shit.”
You tweeted a list of monologue joke transitions you compiled over years working on Conan. Things you can use after the setup. Phrases you can use to sort of kick-start you to the punch line.
If you were to just look at a ton of monologue jokes, you could see all of the transitions. The second sentence always starts with “When.” So I just compiled a lot of them and kept them together in one document. But they aren’t state secrets. If you listen to a monologue, you can pick out the transitions.
Can you explain how some of these are used?
Like “Take that,” which is, if you’re stumped on something, one that allows you to restate it in a different way. Sometimes you’re like, “I don’t know where to go with this one.” And then it’s like, the joke’s already in the setup and you just kind of restate it.
Here is a terrible fictional example. It’d be like, “This penguin did this thing, so take that, penguins who do that thing.”
Exactly. When you look at the transition list, it helps to take you out of your habits. My habits with political jokes is, I tend to be a little heavy and pointed and not ha ha. Conan’s really silly, so anything that gets me just in a sillier direction is good, so I’ll just start scrolling through these and maybe I won’t use one of these exactly, but it’ll just move my brain one degree. Like, “Upon closer inspection,” which allows you to go left or right because you’re gonna say something else happened. “In keeping with tradition,” “In keeping with regulation,” “Without giving too much away,” “It’s better than his usual response” … they just help you curve. If you look at premises, the next line, the next word will keep you in a straight line, so one transition will have you curl up, one will have you curl to the right, to the left, underneath, and all these directions your brain doesn’t normally go.
Yeah, because it’ll either bring you back to restate a version of the setup or bring you right or left to bring up a lie that’s unrelated or forward to sort of escalate the absurdity of a thing.
This is somebody else’s that’s not mine: “Later, when the cameras were off.” I was like, Oh, that’s a way to just totally void what a person says. Especially a Trump statement that is so ridiculous that you can’t amplify it. If you can just take it around a different way, it’s very helpful.
As I told you before, I wanted to apologize for something. A few years ago I wrote a piece about Ali Wong’s special.
In the piece, I made it seem like she was the only comedian ever really to do stand-up pregnant.
Yeah. I didn’t know that was you. But also, that was the general consensus. It wasn’t just Vulture. That was how it was presented.
I think, like, anything with comedy more recently, we oversubscribe how revolutionary it is.
If I were to rephrase it, what I think is interesting is, she did this thing that is not actually that unprecedented. As you noted, you were doing sets at the Aspen Comedy Festival pregnant.
Oh, yeah. I flew to Alaska six months pregnant. Cory Kahaney did her half-hour on Comedy Central pregnant. Lisa Landry did. Kira Soltanovich self-released a special. She was seven months at the same time. Kerri Louise. Those are just friends off the top of my head.
But I think what is true and different was how people really latched onto it.
Yeah. It was cool that people liked it, instead of thinking of it like, “Eww” or that it was weird and awful. People liked that she was pregnant. I’m pretty sure Lisa Landry hid it. She was six months out. She just pretended it wasn’t happening. The fact that Ali could be aggressively pregnant was really cool.
I bring this up because it reminds me a lot of what you often talk about on your podcast.
I love that there’s a boom and that, unlike the last one, it doesn’t seem temporary. It went away. But this feels a little more permanent. It’s just a shift in what Americans enjoy, which is great. And I’m glad I never quit. I know some people that did quit and that they’re sorry they did.
We’re thrilled at all the opportunities women have and jealous that we didn’t have those opportunities when we were at the age that Hollywood likes you to be. Which is painful — there’s nothing I can do about it. We know it’s not good to live in that anger, but sometimes you’re like, “Ohh.” It took so long to headline on the road, and now we see female comics that are like five or seven years in and they’re headlining. It’s like, “Oh, my God.” They just didn’t allow it.
In the piece you wrote in the New York Times about the culture that supported Louis C.K., you talked about how there were clubs that wouldn’t even think to book a woman as a headliner for most of your career. Now they’re more likely to be like, “Yeah, of course.”
They’re not all “Yeah, of course” necessarily. It’s weird. Jackie has been getting people to send her screenshots of calendars, and the male-to-female headliner ratio is still pretty grim. But, at the same time, it is frustrating. I felt like, “I’m never gonna be able to headline until I’m like 40 or something.” It’s just different now. Not all of them, and there are a lot of female comics that are still struggling with extra sexism that their male counterparts aren’t, but a lot more women get put on a track of “You’ll do this for two years and then you’re gonna headline.” It happens so early in their careers. It seems like the industry’s more excited about them. Whereas we just had to keep yelling and seeming like we were always in a bad mood.
In general, what’s the point of a late-night set in 2018, now that we are so far removed from doing The Tonight Show Starring Johnny Carson and becoming famous overnight?
It’s like a little nugget — for me, as I don’t do a ton of road work. I just do road work on hiatus weeks. Building an hour is a totally different thing to put together than a five-minute set. It’s a lot easier to put a five-minute set together in New York or L.A. where you’re doing lots of short sets. You’re just trying to get the jokes as compact as possible. It’s easier to put together a short set. I do wanna put out an album, but I need a couple more late-night sets worth of time. Little chunklets to put together.