In 2008, Iliza Shlesinger became the first woman and youngest comedian to win NBC’s Last Comic Standing. Seven years later, she remains one of the best female stand-ups in the country. Her newest special, Freezing Hot, is available to stream on Netflix starting today. Iliza spoke to Playboy about women, relationships and her television aspirations.
Some of the stuff you talk about in your special, Freezing Hot, such as women being obsessed with fall, loving things made from pumpkins, etc., are things that have been put under the “Basic Bitch” umbrella that’s exploded on the Internet in the past year. What’s your opinion about that whole phenomenon?
I think it’s a ghetto phrase that upper-class white girls like to adopt. I try not to be negative towards women. I don’t see what makes you so basic if you’re doing something other people are doing. I think that’s what makes comedy relatable. For me, it’s more about, “You do these things, I do them too,” and I tell people it’s okay for them to like this. It’s okay if you act crazy or it’s okay if you say these things to your boyfriend because we all do it. When you let the audience know that you’re thinking the same things they are, they feel a sense of camaraderie. I like to think that my stand-up creates a sense of warmth with the audience. It’s not about calling people out, it’s about identifying with them.
It’s interesting that you talk about letting women know it’s ok to do certain things or feel certain ways because you wrote an article for XoJane about your sociopath boyfriend who lied to you about his mother having cancer and a bunch of other things, and the point you made was for women to not feel dumb or embarrassed if they ended up in a similar position. How did you end up writing that article and what was the reaction to it?
They approached me to write something and I pitched them one or two things and I either told that story or someone heard it and they wanted me to write about it. I said if I’m going to write about this, I can’t have a word limit and I can’t have someone edit it. Because I had some weird experiences with other girly websites where you submit stuff and they’ve re-written your punch lines and it’s not funny. For this, it wasn’t so much about being funny. When I originally told it on Joe Rogan’s podcast, I was shocked at the amount of people who not only supported me but also were just kind about it.
I did write it for women out there, and even guys, that have had something bad happen and tell them they don’t have to hide just because there’s some internet trolls that are going to call you names. I received a lot of messages from people saying, “Thank you for writing it. Here’s my story.” And it helped them. Art and comedy are about sharing and healing. I certainly didn’t do it to get a book deal. Am I going to write a screenplay about it? Of course. But we’re also living in an insane age where a show like Catfish is very popular. It’s amazing how many sociopaths are out there.
You also launched your own podcast, Truth and Iliza, recently. What motivated you to do that, besides every standup comedian starting their own podcast nowadays, and how do you make yours different?
I figured a podcast is a great way to get your voice out there and to advertise yourself even when you’re not on the road. I don’t listen to a ton of them, but it seems to be a male-dominated thing. And I’m certainly just as funny as any guy. When you do a podcast, it’s not about you being funny. It’s about listening and perspective. I don’t think a lot of comedians understand that. And the ones who are able to do that well succeed. I didn’t want to do a sex chat thing and I didn’t want to talk about relationships. I love to talk shit. And I wanted to do a podcast about things that annoy me because everything’s always about positivity and what’s good. No, comedy’s about observing and complaining. And so we get together and complain. And it can be about anything from your drink at Starbucks to a grievance you have with society. And what I find is, and Hitler also found this and Henry Rollins and there’s plenty of quotes about this, a common hatred unites people. It’s just a fun platform. I had Jay Leno on to talk about pet peeves in comedy. I had Cheri Oteri on yesterday. To hear these people that you looked up to at one time and listen their insights on comedy and every day life, I think it’s a cool thing to be apart of that and facilitate that.
You mentioned the male-dominated podcast world, which can also be related to the late night television world, which is also completely male-driven. Do you have any ambitions to host a show like The Tonight Show?
Yes, very much so. It’s a very tough thing to get into. I’ve done honestly no less than five late night pilots. And that’s something people don’t see behind the scenes. People don’t see the two pilots I make a year because they don’t go [to series]. It’s a goal that we strive for every year. And you need to make an imprint. You can’t show up and say, “I’m a nobody with no following.” So it takes years of that to build a brand somehow, and everybody’s got a different way of doing it. And hopefully I’ll be next on one of these lists some day.
Speaking of pilots, I just read that you’re developing a comedy for ABC. What’s it about and what’s the status of it?
It’s me and I got Cindy Chupak, who helped create Sex and the City, to be my showrunner. We’re about to turn in our final draft to the network after one more round of notes. A lot of shows out there are obsessed with the concept of 20-year-olds and 30-year-olds dating. And when it comes to women, everything’s about relationships. At my age you’re supposed to be married and have kids, but I just felt that I’m married to my career and that’s what drives me. And for some women, getting married is what drives them and that’s ok too. So I wanted to focus on my career as a comedian. So I took it back a couple of years and made myself a little less successful. It’s about that decision to pursue your dream or take the easy road; to stick to comedy or take a job to support yourself the rest of your life. To take a risk on yourself or go with the sure bet, which I think is an identifiable, universal theme. In the pilot, my character won a reality show but it hasn’t done much for her career. In reality, winning Last Comic Standing was great and it gave me a career. But I’m not selling out Madison Square Garden. So it’s all coming from the concept of every time you think your big break is happening, it doesn’t.
You say you’re married to your career, and you also discuss marriage in Freezing Hot. Is marriage something that’s on your mind?
I’m a little shocked that I’m not married, but it’s not something that concerns me. I’d rather be happy than just be married, and I’m not trying to knock women who are married or have kids, I just think we all have to get out of each other’s lives and stop our obsession over whether someone’s married or not. It isn’t a pressure I’ve ever felt from my family. The only time I’ve found people have something to say about it, and it’s nothing against you, is a man in an interview. Not just an interview. I’ll be in a meeting and someone will say, “You’re 31. Why aren’t you married?” Number one, none of your business. Women don’t ask me that. I’d love to be married. Happiness is a goal, and if it turns out I need to live with a street mime in a hut and that’s what makes me happy, probably won’t, that’s okay.
The older you get, the objective changes. It’s not like in your 20s where you’re like, “Oh I’ll be with someone and we’ll have fun.” But when I got done dating the sociopath, I did just want to have fun. I refused to let the next guy pay for my residual feelings. So I took step back and let guys know, “I’m only going to have sex with one of you because I’m not trying to get a disease. But we can hang out, date, go on vacation, whatever. But I’m being upfront, do not expect anything from me.” And for men, that honesty goes a long way. I’ve done this a lot. My friends make fun of me about this. I’ll go out with a guy and say, “I’ll get drinks with you. I’ll make out with you. I might take my shirt off, but I will not touch your penis. Keep it in your pants.” And every guy says okay, and no one’s ever pressured me because I’ve been upfront because men are very black and white if you’re upfront about it they won’t pressure you about it.
Finally, tell the Playboy readers why they should watch Freezing Hot.
You should watch Freezing Hot because I’m observant comedian who defends both sexes while still ripping on both them. It’ll feel like you’re talking with your best friend and being made fun of by your best friend all at the same time.
Iliza’s new special Freezing Hot is available on Netflix starting today.