Comedian Kate Willett Breaks the Rules in a New Comedy Special Loopholes

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Comedian, actress, and writer Kate Willett tackles topics including gender, feminism, sex, BDSM, accidentally becoming domesticated during the pandemic lockdown in New York, and a healthy dose of politics in her new comedy special Loopholes, currently streaming on Apple TV and Prime Video.

Kate has appeared on the Late Show with Stephen Colbert and Netflix’s Comedy Lineup and tours across the country. She’s the author of the Audible Original “Dirtbag Anthropology” as well as the co-host of the political comedy podcast Reply Guys. In addition to crafting hilarious jokes for herself, Kate has also written jokes for the iconic TV series Beavis and Butthead.

Kate has toured with Margaret Cho nationally and internationally and has featured with comedians like Kyle Kinane, Maria Bamford, and Greg Behrendt. We had a chance to catch up with Kate and talk all things comedy in our exclusive interview.

Kate Willett Loopholes — Photo courtesy of Kate Willett

What is the significance of the title Loopholes?

So, you know, I was thinking about how there's all these like rules for what women should be, whether it's rules that are coming from a traditional perspective, like you're supposed to be feminine and docile and then there's also so much pressure that's put on women from other directions to be really sexy or to be a feminist who's just killing it in your career and stuff like that. But, you know, actual life is so much more complicated and I was just thinking about all these different sets of rules and how we're always just trying to find the loopholes to them.

How did you get started in comedy?

I started about 11 or 12 years ago in San Francisco, in that comedy scene, which is a very fun scene. San Francisco, especially at that time, was such a weird place. You'd be on a show with like a mime and a trapeze artist or whatever. And so, I started performing all over. I had a show in the basement of a video store for a while, which was really cool and I just built a really good community there before moving to New York.

How long have you been performing?

I've been performing for…I think it's probably been 12 years at this point.

How would you define your comedic style?

I would say I'm very joke based, which sounds funny to describe comedy that way. But there are some performers who are very physical, and I love that kind of comedy, but mine tends to be more about writing jokes and telling stories. My sense of humor is pretty dry. I'm very honest in my work. I try to be very personal and I would say that vulnerability is something I place a high priority on in terms of revealing and personal comedy versus something that's more observational, even though I love all those things too. I'm just trying to figure out how to describe myself.

When you're going to put together a special like Loopholes, what is your process?

I usually write bits as standalone things and then I'll probably wait until I have about 70 to 80 percent of those done that I would need to make an album or a special. And then I would start looking at, okay, what are the themes here? What was I thinking about for these past couple of years? What were the topics that were running around in my mind and what was my life trajectory? And then I'll write. I'll write the stuff that would tie it together or think about how it ties together. There are other ways to write a special – some people know exactly where it's going from the beginning. And I would totally write something that way. Maybe that's how I'll approach it next time. But the past few times, I've sort of been writing and then analyzing, like, where was I? What was I trying to say?

Who were your comedic influence? I know you toured with Margaret Cho, who is amazing, but who else are some of your other influences?

Margaret Cho is definitely an influence. Maria Bamford has been a huge influence to me. I love Ali Wong. This is old school, but I would say Marc Maron was a huge influence. He was my favorite comedian when I started comedy. I really loved how raw he was, honestly. I mean, he still is. He's still a really great comedian.

There are a lot of comedians I love that I wouldn't necessarily say I'm similar to. Joe Pera cracks me the hell up all the time. He's so funny. In terms of really good comedians who just inspire me to love comedy and to show up and do it another day, there are definitely some.

Do you have a really good bombing story?

I don't believe a good bombing story. I mean, I certainly have bombed a lot in my life. I've done a lot of shows, especially when I was first starting out, where we call them ambush shows where the audience does not know that there's going to be a comedy show. Like, they went to a sports bar to watch a game and then the game gets turned off and they're forced to watch comedy and they're really mad about it. So, most of my stories have been like that, but I don't know if there's one that is a standout.

How do you deal with hecklers?

You know, weirdly, I don't have hecklers that much. I think there's some kinds of comics that attract hecklers more like people who do a lot of crowd work and post a lot of crowd work videos. The audience is very trained to think of it as a conversation where their participation is required. But, you know, I think because they're not super crowd work, I don't get heckled that often but there are times when somebody is drunk and they really want to talk or whatever. A lot of times if you just have an interaction with them, go back and forth and make fun of them a little bit, they're satisfied after that, you know, just a little bit of attention and then it's like, “Shh, be quiet.”

Do you think comedians that encourage crowd interaction are ruining stand up or affecting it negatively?

No, I don't think it's ruining stand up. I think it's a little bit of a different art form. Sometimes, it's more like improv in a way. What they're doing takes a lot of skill and creativity in terms of being really funny in the moment and not. I also think that there are comedians who are just heavily into the writing, like, John Mulaney. He's one of the greatest comedians of all time. I'm not treading any new ground there, but his style is more like he has jokes and then he'll have a few moments kind of built in for crowd work and his work and I think every comedian has their own balance.

I lean I think more towards prewritten stuff, but I like having crowd work as an option if something happens or especially if you're doing a show that's late on a Friday night and you're like, I’ve got to wake these people up, you know?

You wrote for Beavis and Butthead. What is that experience like being in a writer's room for something like that?

Well, for Beavis and Butthead I did punch up which is after the script is written they'll have stand-up comedians come in and add some jokes. That's very fun – at least how we did it for Beavis and Butthead was just a few comedians in a room just riffing on different jokes they could say – which is for Beavis and Butthead is so fun and silly because the minds of Beavis and Butthead is a fun one to embody.

Can you tell me a little bit more about your podcast Reply Guys?

Well, so Reply Guys is kind of transitioning to something else right now. I'll be back with, with it in early May. There'll be like version two. Reply Guys was a leftist feminist podcast where we focused on leftist and progressive perspectives. Sometimes journalists, sometimes people running for office, sometimes like leftist or progressive comedians.

I'm doing a new podcast called Ruining Dinner, and it will be very much in the tradition of Reply Guys, but it'll be people coming on and instead of just political things, it'll be people talking about the subject that they most make things awkward with. A lot of times that is going to be what somebody is most passionate about politically, the issue that is the most controversial or important to them.

But I also wanted to leave space for people to talk about things that maybe are a little more oriented towards things with their family or relationships. I think it's still going to be probably heavily leaning towards progressive or leftist issues, but I have so many funny friends who are comedians and writers that I wanted to give people a chance to talk about some other stuff too that's also important to them…maybe LSD, maybe sex.

Besides the podcast and specials, what is on your bucket list of things you still want to accomplish in your career?

I’d like to make something either for TV or film. I haven't had a lot of experience with visual storytelling and I do think it's so cool, just developing characters that really have so much. I don't know why I'm describing what TV and movies are to your audience. They surely know, but I think that that would be really neat.

Kate Willett Answers the Socialite Seven

Who would you love to work with?

Who would I love to work with? Oh man, I'm trying to think. That's such a good question because it's so open. It's not even like just comedians, it could really be anyone. Let's see…I am a big fan of a bunch of different writers. I think that it would be so cool to get to do a comedic adaptation of like a novel I really loved – or maybe even like a nonfiction book, like Naomi Klein. I love her so much. I'm reading her book Doppelganger, and it'd be very cool to make some kind of movie version of that.

What are three things you can't live without?

I'm not going to be the person that says food or water. I love my cats. They are such amazing little guys. I love going on a camping trip every summer as a chance to clear my head and I love caffeine. I love being able to just start the day with some makeshift ADD medicine.

What is your biggest pet peeve?

I really don't like it when people are…I mean, this is probably why I wanted to do the podcast that I did. I don't like it when people are so non-confrontational that it just becomes being cowardly. I don't like it when people pretend to not have opinions about things that they actually know what's right and wrong.

If you could wake up tomorrow with a talent or superpower that you don't have, what would it be?

I was watching some birds the other day and it would be so cool to just be able to fly around, to just be able to zip over to my friend's house through the sky. My boyfriend lives in Bushwick and no matter which way I go, whether it's driving or taking the train for an hour, it'd be so cool to just fly on over there.

If they made a movie of your life, who would you want to play you?

Oh, good question. I think the first person that comes to mind is maybe like Natasha Lyonne. She's such an interesting actress She's good at playing weird ladies, you know?

What overused word or phrase would you love to eliminate forever?

It's complicated. I think, yeah, I would get rid of that one.

What is the best piece of advice you've been given?

Man, that's such a good question. I like the concept of the middle path from Buddhism. I think that there can be a tendency to feel like there's so much urgency to do things one way or the other and I like trying to find the middle path. I realize this kind of contradicts what I said about moral situations. This one is more like for emotional situations you know, to find that middle ground with people, I think.

Loopholes is now available on Apple TV and Prime Video. Follow Kate on Instagram.

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