Why Natasha Leggero Will Never Do Another Comedy Central Roast (2024)

Natasha Leggero got her first big break roasting D-list celebrities on Chelsea Handler’s talk show. Later, she moved onto the A-list with breakthrough performances at the Comedy Central roasts of James Franco and Justin Bieber. On Netflix’s The Honeymoon Stand Up Special, Leggero and husband Moshe Kasher brought other couples up on stage to give what they framed as relationship advice, but felt a little more like mockery.

Now, Leggero has set her comedic sights on a new target: houses.

Along with her friend and fellow comedy writer Dan Levy (the one who created the sitcom Indebted, not Schitt’s Creek), Leggero has spent much of the past year co-hosting House Hunters: Comedians on Couches Unfiltered, a discovery+ streaming series in which they invite comedians like Seth Rogen, JB Smoove, and Whitney Cummings to watch that popular HGTV reality show and riff jokes from home.

“My husband said not only is it the easiest project you’ve ever done, it’s the easiest project he’s ever heard of in Hollywood,” Leggero says on this week’s episode of The Last Laugh podcast. And while a lot of jokes are about the houses themselves, the prospective buyers are also subject to plenty of ribbing. “I have a feeling that when these people agree to do House Hunters, they sign away any rights they have to complain,” she adds.

More than anything, Leggero says that the show has given her an outlet to be funny and spend time (virtually) with other comedians during a year in which the coronavirus pandemic has forced her off of the road.

And since she can literally do this gig from her couch, it’s allowed her to spend way more quality time with her young daughter, a subject she tackled at length on last December’s Yearly Departed special on Amazon Prime Video. “After being quarantined with her for eight months, I’ve been thinking about sending back my Wayfair furniture with a fun surprise,” she joked.

“You could always tell when a male comic had a kid, because all of a sudden you’d go to their website and they were booked solid for the next year and a half,” Leggero tells me. “They want to get out of the f*cking house! But for a mom to have a stand-up career, it’s uniquely challenging.” While she’s “not saying people can’t do it,” the comedians says stand-up “definitely became way less appealing” for her after she had a kid.

“I miss going on stage and killing,” she admits. “But you know, that doesn’t happen all the time.”

Below is an excerpt from our conversation and you can listen to the whole thing right now by subscribing to The Last Laugh on Apple Podcasts or wherever you listen to podcasts.

I think that the first time that I really took notice of you in a big way was at the Comedy Central roasts, starting with the James Franco roast in 2013. And then you did the Justin Bieber one a couple of years later. Was that a big deal for you at the time?

It was a huge thing for me to do. It was one of those things that’s extremely intimidating because it’s like, “Oh, I’m gonna go make fun of A-list celebrities I’ve never met before?” Everyone could take a joke but it was extremely intimidating. And it’s one of those things in your career where you’re like, “OK, I’m afraid of this. I’m terrified. I’m going to try to rise to the occasion and be so prepared.” It sounds very cliche, but it’s really about preparation. You have to be so prepared and every time there’s a point where you’re like, “Well, I could go do another set here or I could just stay home, I’ll be fine.” Always go do that extra set, always go try out that extra joke. For something like that, that’s the only way I’ve ever been able to get through it, just by doing the work so hardcore.

With the roasts, there are kind of two levels to it, too. Because you have to come in and make fun of these A-list celebrities that you didn’t necessarily know. But then you’re also coming in as the newcomer, so you have to sort of play that role. What was it like for you to then be roasted as well, especially in that first one?

I was terrified. I was like, “OK, so I’m a woman. So I’m either going to be a whor* or old.” So I was like, well, I’m not 20, but there were other people who were older than me.

That was the year when there was a lot of controversy around Sarah Silverman, who got all of these “old” jokes when she was what like 42 or something, right?

Yeah, and Sarah was so funny and looked so amazing. So I somehow escaped that, because nobody wants to go up there and have men say that your pubic hair has spiderwebs or whatever. They can just be so mean to women. And then I was offered the roast a third time and I had just had a baby and I was like, you know what? I don’t think I’m mentally prepared for jokes about how my kid would have Down syndrome because I’m such an old hag. You kind of play through the worst-case scenario. So I was like, you know what? I think I’ve done it. It was fun.

It was a conscious decision to say you don’t want to do any more of these? Or would you go back later do you think?

I feel like I’m good. But you know, it is all in fun. But again, the old roasts were more like friends ribbing each other. Now it’s like Jonah Hill. I didn’t know these people.

It’s fascinating to watch the roasts because they kind of exist in this world outside of “cancel culture” and things you can’t say, because it really is anything goes. There’s not a lot of holding back at these roasts and it doesn’t seem like there’s a lot of fallout either, right?

I don’t know, I think that comedy is evolving and changing. And what was hilarious 10 years ago—I think a lot has happened and I just have to feel that we’re growing in compassion as a culture and as a species and that art will reflect that. There’s a lot of things that I didn’t think about, that I would just say ironically two decades ago that now you’re like, “Oh yeah…” And look at what’s happened. Gay people have more rights and even mock racism that was popular 20 years ago, people are like, wait, why would I say that? That’s not funny, that hurts people. I just think that maybe it takes a long time and it takes movements like this to realize it. And anyway, the point is I don’t want to do any more roasts. [Laughs]

You did sort of have your own mini experience with “cancel culture” though, right? The SpaghettiOs Pearl Harbor thing on New Year’s Eve was kind of a story for a while. And I think you handled that really well in the way that you didn’t reflexively apologize for what was really kind of a silly joke, even though it created some outrage. What did you learn from that experience that you have carried forward?

I mean, that just felt like old Republicans lashing out or something. And it was pre-”cancel culture.” I feel like getting death threats from old people with guns because you made a joke about how men have to gum their SpaghettiOs, I don’t know, what can you say? But I do feel like comedy is always changing and evolving. I was on Chelsea Lately for like a decade and that was what the current culture was, making fun of celebrities, making fun of these people you’ve never met, maybe they’re overweight, whatever it is. And every day we would just be making fun of these dumb celebrities. I don’t really feel like doing that anymore. I don’t really see that happening around me as much. That’s what’s fun about House Hunters is like, OK, let’s make fun of houses for a while.

Do you think getting more celebrity yourself makes you think differently about making fun of celebrities?

No, but getting more people who will go onto your Instagram and be like, “You’re an ugly old bitch, die’ or whatever, it’s like, ‘Oh, did I used to do that to Khloe Kardashian?’ I mean, I would have said something more clever. But I just feel like that was really big for a while and now we’re moving into new things. Maybe we’re moving into a world of more absurdity, which I think would be really fun. Who knows where we’re going, but I’m excited.

Next week on The Last Laugh podcast: SNL alum and star of NBC’s ‘Mr. Mayor,’ Bobby Moynihan.