On having fun

I was re-listening to the Normal Gossip episode that you guested on in 2024. Have you learned anything about your own joke-telling style or writing style from being a podcast guest?

I’ve learned that I can be pretty malleable. That’s something I really enjoy cultivating and practicing, from going on Normal Gossip and fitting the tone that Kelsey [McKinney] and Alex [Sujong Laughlin] established, to going on Wait Wait… Don’t Tell Me!, which is radio. Being able to switch between tones and pacing, and being engaged with the hosts in the way the show demands, is a real joy to be able to do.

How has the format of a show as unusual as Wait Wait… Don’t Tell Me! encouraged you to try different formats in your creativity?

One thing I always enjoy is variety. When someone asks what I want out of a career, I used to always say that my goal was to do whatever I want all the time. I like the cross-training creatively between, “I’m going to go on a radio show with a live audience of several hundred people, or a few thousand, and it goes out to five million listeners,” or I’m working at Desus & Mero, or doing deep, in-depth, long-form comedy writing for Last Week Tonight, when I was there.

I don’t just sit with my notebook, write jokes, tell them on stage, then go back to my notebook by myself, write more jokes, and tell them on stage. I have all these different, fun experiences, and I think part of it is I like the different kinds of work. I like not burning out on one thing. I also like collaborating with different people.

How did you chart a path toward doing whatever you want to do?

It’s been a combination of being open to weird things and willing to do a lot of different stuff. I’m really bad at five-year planning, so I’ll say yes to stuff that might not be on a linear trajectory in one direction, but that’s fine to me. I say yes to stuff when it seems fun. I like the stability of being on a long-term job, but while I’ve been between longer-term writing gigs, I’ve embraced instances of, “You want me to go to this city for one day, and the money is fine, but it’s people that I really love.” I’m always inclined to do that, and I’m much more skeptical of, “This pays a little better but is attached to some company that I don’t care about or don’t like, just for the sake of some promo stuff.”

How do you get something like your piece for Esquire on doing the Tough Mudder challenge together? What doubts do you have to quell about its ridiculousness?

That came about because Wheaties sponsored me to do the Tough Mudder. The experience fell into my lap. That more corporate sponsorship paid the bills, but I’m not morally opposed to the idea of Wheaties, so it wasn’t too hard—except that I had to do a lot of intensive training.

I love a commitment to the bit. I don’t shy away from discomfort in professional situations, but I do more in personal situations. I think it’s fun to get that opportunity of, “Do you want to do this? It’ll pay some bills, and it’s not an experience you’ve ever had before.” I’m pretty easy to get a hold of, so if people want me to do something, they don’t have a hard time putting a bug in my ear, and then it’s [a question of], “Do I have the time to spare and the energy? Is it worth it financially? Is it worth it creatively?”

Your comedy special, Positive Reinforcement, makes it clear that you’ve fully stepped into your kind and wholesome persona. To what extent is this persona a natural outgrowth of who you are versus a character you’ve cultivated for your creativity?

Who I am on stage, the parts of myself I highlight on stage—it took me a while to get there, but it was natural. I tried a bunch of stuff when I was starting out. I was 19 when I started doing stand-up, so I wasn’t really a person yet all the way, and it took me a while to get it together and figure out who I am, just moving through the world. That came hand in hand with realizing, “That’s who you are on stage, too.”

I think “wholesome” is such a fun word to use, because I don’t curse much, but it’s not clean. There’s this interesting place where I live creatively: I’m pretty friendly, but I’m also a grown-up that doesn’t shy away from talking about grown-up things. It took me a while to find that balance of the gentleness I project. Early on, I was doing the moves of stand-up comedy without having as much of my own heart and mind in it. It’s a balance between that, learning the chops, and just getting better as a performer, and hopefully as a person, too.

Have stand-up, creativity, and writing been vessels for you to learn and discover who you are, or vice versa?

I think vice versa is probably more true. Through living, I’ve learned who I am as a performer… Doing a lot of performance, I’ve gone a lot of places and learned about myself, and met a lot of different kinds of people and had to make creative and professional choices that don’t strain who I am but make me ask, “Is this a choice that the person I want to be makes, and is this the work that the person I want to be does?” I learned more about making comedy by being a person than I learned about being a person by making comedy.

Earlier, you mentioned that you love collaborating. Can you say more about why?

I love being part of something bigger than what you could do on your own. That’s how really special, wonderful things get made, and I always feel grateful to be a part of something that incorporates other people’s talents that I don’t have. [When I was] making a standup special, I brought in a director who’s my buddy, Chris Werner, who I worked with at Last Week Tonight, who is a producer and director there. He put together this wonderful team. It took a whole mess of other people to build the set and operate the cameras, hair and makeup, all that stuff. I really value everybody’s contributions to a thing that points directly back at me and has my name on it. That’s something I learned from working for other people who feel that way about the teams they assemble.

How do you know when it’s time to move on from one of your creative pursuits to another?

I’m pretty bad at letting things go, and I also have this New England-y Puritan mindset about work, about not quitting something until you have the next thing lined up. I left Last Week Tonight when the opportunity to move over to Desus & Mero as a writer and producer presented itself. I had gotten to a point where I felt like I had learned the ropes. I really loved that job, [but] I had gotten to a place where I was like, “I would like to learn more things, and I would like to learn the production side of things.” Last Week Tonight was hardcore writing work. At Desus & Mero, because I worked in TV and had worked for a show that was so acclaimed and its own special thing, I got the opportunity to take on some new responsibilities that I had to grow into a little more. That was really exciting to me. It was really special to get to learn new things from new people.

How is your day-to-day is structured when you’re full-time with a writers’ room versus what you’re doing now with individually spearheaded projects?

I’m trying to use this flexible time to do stuff that’s really fun and exciting creatively, and see how long I can keep that balloon up in the air… It’s been nice that I’ve been out of writers’ rooms for a few years and I haven’t had to take on anything that’s a real slog to keep the lights on in our apartment and keep our pug fed.

I’m up in Boston now. My wife, Maris Kreizman, launched her book last night in Brooklyn, and she said, “I’m doing an event at the Harvard Bookstore on July 2, and they asked me to bring you as the interlocutor.” That’s something I can do because I’ve been more freelance, more like a roving comedy bandit for the last few years, and it is really special to me to be here and do this.

I have some bigger TV projects that I’m hoping pan out in the long-term that aren’t super far along or public yet. I would like to go back to a bigger institution at some point and work within [it] if it’s an exciting, fun thing. But it’s been so nice that when Wait Wait calls and says, “Can you fly to Portland, Maine on a Thursday night to do a live recording?” I don’t have to ask for time off.

What attracts you to potentially going back into a bigger institution?

I think it’s the love of collaboration we talked about before. It’s floating into another exciting, creative possibility to make something different than stand-up, radio, or occasional little voice gigs—all of which I love to do. It’s fun to have a stronger hand in something that’s really big. And then, financially… I’m not a celebrity, so touring is only going to be so lucrative, at this point. I’m at a point still in my career where it’s more financially sustainable to be a part of writers’ rooms and working on projects that way, as opposed to going, “I make as much money as people put in my pocket for being me all the time.”

I’m curious about your experience writing your book, Nice Try. I’m somebody who writes a lot of article-length things, and sometimes I’m like, “What if I wrote a book?” And then, I’m like, “How?”

I’d co-written a book that came out in 2015 [called You Blew It!], and I learned a lot. My friend Joe Berkowitz and I really held each other accountable for meeting deadlines and getting stuff done on time, so it wasn’t a super strain to complete this silly humor book. When I was working on my essay collection, I set up an arrangement with my editor that I was going to hand her essays in batches every couple of months, and that would keep me on track. I really did dread doing this giant project with no feedback. Having that accountability really helped in being like, “Someone expects to read this. I will expect feedback in a timely manner.” Even just telling myself that as a premise made me stay on course.

I want to put one final question out there: if you have anything more to say about creativity, go for it.

One thing I’ve always believed in—I don’t know if I’m stealing this from somewhere—is, even when you’re working on a full-time creative job, it has always helped me to have stuff I’m creatively splashing around in on my own. It’s nice and energizing to be working on stuff that nobody’s asking for, and [for which] nobody has set parameters other than yourself until you decide, “I’m going to make this a job, too.” Even at Last Week Tonight, when I couldn’t tour, I would still do a lot of stand-up because it helped me to go out at night and be like, “Now I get to say the words in whatever order I want, instead of being part of this bigger whole.”

I’ve put forth this face of a real collectivist creative person, but I do also have a little of that ego, not just in terms of, “I like when people laugh and clap to my face,” but of, “It is fun to do a project that comes out the way I want.” It’s not necessarily that I need to be the boss at a show, but it’s so gratifying to have an outlet that’s mine rather than accountable to an executive producer, a production company, and a network all the way up. To just go, “I’m going to do it the way I want, and then I’ll find partners who believe in that vision and want to help me bring that to life.”