Balancing Standup and Writing for ‘Late Night’ with Michelle Wolf

Not many comics would close their New Faces Showcase at the Montreal Just For Laughs Festival with a three-minute joke tying together men’s masturbation habits and JFK’s assassination. That one’s got a high degree of difficulty.

Michelle Wolf made it look easy.

Wolf, 29, was among the standouts last month at Just For Laughs, the comedy industry’s premiere festival. The NYC-based comic, who’s also a writer/performer on Late Night with Seth Meyers, even earned herself a slot performing in front of 3,000 people for Seth Rogen’s televised gala. Not bad for someone who’s less than 4 years into stand-up.

I had the opportunity to chat with Wolf after her New Faces showcase to talk about her former career on Wall Street, working on Late Night, and using Twitter to come up with jokes.

So you used to work on Wall Street? For how long?

Almost four years between Bear Stearns and then JP Morgan.

You must have liked it somewhat. 

No, I didn’t. It was good money and my schedule wasn’t so crazy that I couldn’t do comedy. Because I didn’t start comedy until after I started working. I had no intention of doing comedy.

You weren’t into comedy in college or anything?

No, no. I was either going to go to medical school or get my PhD in exercise science. I wanted to take some time off and a lot of my roommates got jobs on Wall Street and said I should get one so I did. I started improv about six months after I moved there and took classes at the PIT and UCB at the same time.

Just on a whim?

My friends came to visit me in March of 2008 and we went to a taping of SNL. I’ve always been such a huge fan, and afterwards I was like, “I want to do something like this.” So I Googled everyone on the cast and most of them started in improv, so I was like alright, “I’ll sign up for an improv class.” Then after my first improv class I was like, “This is the best thing in the world. I love this.” I just wanted to do something that involved that. Then after a couple years of improv I eventually started to do standup and then switched over almost completely.

Growing up, were you into comedy? 

I was super into SNL. I used to quote the sketches all the time. I remember trying as hard as I could to stay awake to watch, and I’d almost always fall asleep during Weekend Update because I was too young and dumb to understand news jokes. [laughs]

What led you from improv to standup?

Actually some of my friends I improvised with suggested I get into it. The PIT, in order to kind of shoo me in that direction, let me audit this standup class Tom Shillue was teaching. He’s so fantastic. After I took that class, I guess a couple months after that was when I started to get into it hardcore where I started to go to an open mic every night. At least one mic a night.

For how long?

I’ve been doing standup now just under four years. I think for like two and a half years. Now I probably still go to a mic like once a month or something, but I’m lucky enough to get on enough shows. And I also don’t really have the time anymore. I’m very happy if I can do one show a night. On the weekends I’m like, “Please, as many shows as possible.”

Do you still try to do a show a night when you’re writing?

For the most part. I don’t feel bad if I don’t do a show but if I can I like to. Honestly, I’d like it if I could do four shows on a Friday and four shows on a Saturday and take it a little easier during the week. But weekday bar shows are such a good time to work on material. If you can get on a solid bar show and just work on some new ideas that’s really nice to do.

The bar shows are tricky. There are the good ones with built-in audiences and the buzz, but sometimes you go and there’s like four people there.

If you’re at a bar show and there’s only six people there and you’re like, “Guys I’m just trying out this stuff, you don’t have to laugh, but I’ll check in and if you like it and think I should keep working on it, let me know.” I’ve actually gotten some good jokes out of that where it’s like in front of six people and I literally will ask their opinion after the joke. I’ll be like, “But did you like it? You didn’t laugh, but did you like it?” Also learn to laugh.

You don’t do any improv anymore?

We do once a month the writers for Late Night do an improv set at UCB. I hadn’t done improv for maybe a year and a half or even two years when I switched over to standup and now I get to do it once a month with all these people that I love, and it’s super fun.

What’s your role on the show? Do you write monologues, sketch?

I write both. Which is great actually, because you don’t get stuck doing one type of thing. You get to stretch both parts of your brain. We have a great team of people and I’m really fortunate to work with all of them.

How many monologue jokes do you write a day typically?

It depends on the day. We don’t have a set number that we need to write every day. Just write good jokes. I probably end up writing throughout the course of the day 50. Some days more, some days less.

Do you feel like you’ve got a good grasp of what will make a good monologue joke versus a good joke for you to tell on stage versus a good sketch idea? At the end of the day it’s all based on a punchline.

It depends on if it’s a very topical thing, obviously that’s monologue. But there are some monologue stories that are like timeless. Before I started working at Late Night I would write monologue-type jokes on Twitter a lot and there are some of those that I turned into bits that I now do on stage.

That seems like one of the few useful purposes of Twitter. It’s a joke writing machine.

It is. It teaches you to write a very concise punchline. I didn’t have a job from January of 2013 to January 2014 and in that year I just wrote jokes on Twitter everyday, all day. Some of them I’d take to mics that night and other ones I would just throw away, but it really taught me how to write a good punchline.

It gives you a sense of immediate gratification. But also some of my favorite bits have come out of dumb tweets. I think it’s really helpful. Some people disagree.

It’s sort of rare to be good at standup and good at Twitter. You don’t see too many people who are good at both. Different brain muscles, I guess.

Oh for sure. Even when I do stuff, there are tweets where I’m like, “This is going to work on stage. This is amazing, I just wrote the best joke ever.” And then I’ll do it on stage – I’ll do it a couple times on stage – and it doesn’t work at all. It’s never perfect.

Do you consider yourself more of a writer who does standup or a standup who writes?

I like to think that I keep a pretty good balance between the two. I always want, no matter where my career goes, hopefully it goes, but that I am always writing my own stuff. I feel like if you write you will always have a job. Or you’ll be creating material for yourself. I like to think of myself as an equal writer-performer. Standup is so much fun and so rewarding when you actually get stuff to work. When you figure out a joke there’s not really a better feeling than that, where you’re like, “I finally got all these weird pieces to fit together.”

Sometimes it takes a while.

It takes a long time. There’s a joke I’m doing right now that I started when I was in that Tom Shillue class. I could never figure it out and then I was packing up some stuff because I was moving and I saw this index card I had written it on. And I was like, “I should try this joke again.” So I rewrote it and now it works great. I’m like, “This is amazing, I’ve got to go through all my old shit.” But that joke I started three and a half years ago.

Did you tell it last night?

No, I did not tell it in my NINE-A-HALF-minute set. [laughs]

Were they mad at you? 

I legitimately didn’t see the light. Then someone’s cell phone went off in the middle.

It was supposed to be seven?

It was supposed to be six. The night before I went over too. But I did the same set both nights.

I loved your closer about JFK. I was dying.

Thank you. 99 percent of the time that joke goes over very well. One percent of the time, which happened last night, it will end on a groan. And when people groan, I want to be like, “It’s probably because that was you. You were the guy masturbating to JFK.” [laughs]

Your act-outs alone in that joke are worth it.

It’s the creepiest voice, and I legitimately don’t know how guys masturbate.

Well, it’s pretty close.

[laughs] Yeah, that’s a really fun joke to do. I actually like that joke because it mixes my favorite things to do: have really tight punchlines but also super fun act outs. When I can find a joke that gets all of those things in it, I’m like, “Well this is my favorite joke to do. I love this joke.” And then I will fight for those to work.

You didn’t have a lot of overlap between your set last night and your TV set on Late Night, which was also great, by the way.

I did that on purpose. Thank you, I was so nervous, because if it didn’t go well I just had to keep working there. Everyone just like looking me in the eyes like, “Hey, you did it! We saw it!” and me being like, “Yeah, I did it.” I did that on purpose though. I knew that after this if someone was Googling me I didn’t want them to see the same jokes that they just saw me do. And clearly I couldn’t do the JFK joke on TV. I’m never going to be able to do that joke on TV. It’s so sad.

Before you got on Late Night did you have any other on-camera experience?

No, I didn’t. I think I did a sketch for Girl Code where I played a weird roommate, but Late Night was the first time I was on TV.

How does it compare to being on stage when you do characters on the show?

Honestly, that place is such a nice family of people that you feel so supported all the time that it’s not really that nerve-wracking. I feel like Seth is a huge safety net because he’s so good at what he does that you feel like he would take care of you if something bad happened. Genuinely, the first couple times I was on it, it’s not a big studio, I don’t know if it’s like 150, 200 people…

But still, you’ve got giant cameras on you.

You don’t really notice all that stuff. There’s so much stuff going on. There’s a bunch of different cameras but there’s also monitors and the cue card guys, it doesn’t really seem like cameras are on you. I couldn’t believe it was happening the first couple times. I could not believe I was getting to do this on TV. Because it’s a smaller audience it never occurred to me right away that a lot more people are going to be seeing it than just these people. But you feel like you’re just performing for those people and that makes it a lot less stressful. I can perform for 150 people no problem, then you realize it’s going to be on TV and you’re like, “Oh.”

Do you watch it?

I usually watch it the next day. Sometimes I try not to read the YouTube comments but then I do.

It’s like trying to not look at a car accident.

Yeah, exactly.

How do you decide material that you’re going to do in Montreal? Is it the same stuff you auditioned with? 

Yeah, I had two auditions. The first audition I did a different set than I did the second audition. I did some similar jokes but I changed a couple of them. I essentially did the same set I did in the second audition. I knew at that point that I was already doing Late Night so I was purposely trying to make them different already. I really wanted to pick a mix between stuff that was like “hey this is me” – you’re supposed to introduce people to yourself, so that’s why I did the being single joke and the gym joke, the getting fired joke.

For aspiring writers, [is your advice to] just keep writing every day? Someday I want to hear a writer say, “write when you feel like it and you’ll get hired eventually.”

Yeah, there’s not a shortcut to it. Literally writing every single day even if you don’t feel like it. Just continually trying to be like, “I can write a better joke than I wrote before.” Even if you come up with your favorite joke that you’ve ever written, you can always be like, “I can do a better joke.”

Do you take your work home with you?

I constantly think of both. It’s a constant like, “Oh, I just had an idea for this, or I had an idea for this.” It happens in both places. I liken standup a lot to – I did track in college, I was a high jumper at William and Mary – I liken standup to high jump where even if you jump your best that day, they’re still going to move the bar up and you’re going to get out at some point. That to me is what it is. Yeah, you’re going to do your best, but there’s always another thing to get. That is what I’m constantly working for. I honestly just want to keep getting better at writing jokes. That’s all.

Is it important to learn the structure of writing a sketch?

Yes. You generally want to have some sort of arc in it. If you have a funny idea you can write a punchline and you can break every rule. There are so many rules but if it’s funny you can break them. It’s the same as improv, it’s like there are so many rules in improv but if it’s funny you can break the rules. But I love writing sketches too. Hopefully I’ll write longer sketches, like television shows.

What would be ideally the next steps/goals for you?

I just want to keep writing and performing and just getting better.

But maybe eventually working on your own sitcom?

Yeah, I don’t know. I want to see where everything takes me. I’d love to write and produce my own thing but if something else comes up that I’ve not thought of or an opportunity comes up I’d love to take it. I don’t want to say I want to do one specific thing because I don’t think I actually want to do one specific thing. I want to just see what happens. It’s been super fun so far and I never expected… my life from this point last year is so completely different than where it was. When I think about it, it’s insane. The past six months that I’ve worked on Late Night have been the best six months of my life. I’m so fortunate to get to do what I do. I guess I’ll just keep trying to get better at that so that it keeps going up. I’m very fortunate and it’s been super fun and I’m excited to see what happens.

Michelle Wolf’s standup show: Michelle Wolf: She Needs a Cat is Wednesday, Aug. 13, at the UCB Theatre in Chelsea.

Phil Davidson writes about, performs and produces comedy.

Balancing Standup and Writing for ‘Late Night’ with […]