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Jena Friedman’s Substack · Aug 3, 2026

BRIEF INTERVIEWS WITH HILARIOUS MEN

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Jena Friedman · Jena Friedman’s Substack

If I had a dollar for every time a journalist asked me, “Is it hard being a woman in comedy?” I’d probably make as much as a man in comedy. The truth is, being a woman in comedy is fine, and sometimes it’s really great. I have nothing to compare it to. It comes with the same indignities as being a woman in almost every other industry in America, but at least we have a microphone!

There is, however, one aspect of the job that’s a little annoying: constantly fielding inane and sexist questions during press interviews. If only we could all just do our work and answer questions about that, but no. So often, female comics have to answer questions about anything else: from sexism in society to our male co-workers’ sexual misconduct allegations. It makes me wonder if male comedians ever get similar questions from journalists and if so, how do they respond when asked them?

Inspired by all of the bat shit crazy but completely real questions that I and other female comedians have endured over the years from actual journalists (including notable ones from publications such as The Guardian, The New Yorker and The New York Times), I asked my favorite male comedians the most sexist (but 100% real) questions that I could find, mostly verbatim, with the genders reversed. The results were illuminating.

A note on my methodology: For all of my interviews, I reached out to my favorite male comedian friends. I prefaced my intent in advance (something I rarely do before interviews). Each interview was done individually, via phone or email, but everyone got similar questions. Some responses are verbatim, others are consolidated for clarity.

What’s it like to be a man in comedy?

Jon Stewart: [laughs] It’s golden. Basically men in comedy are carried into the clubs. It’s incredibly pampering, you’re paid in Doge coin—did I even say that right? Doge coin and cocaine futures.

Eugene Mirman: Um, you know it feels fine. It feels like I have opportunities I can pursue [laughs] —I’m sorry you get that question. It’s so outside of what I do that it really makes it clear that interviews for you are probably unpleasant.

Jena Friedman: This is just the first one!

Bob Odenkirk: Uh… perfectly uninteresting, un-unique. It’s uh… what’s it like being a man in comedy? I fit right in [laughs]

Jena Friedman: You’re doing great. It doesn’t have to be funny—

Bob Odenkirk: I’m allowed to be a crude asshole and get laughs from it and let that part of my psyche out in a public way for the sake of laughter.

Patton Oswalt: Sometimes the road can be a little rough. I don’t want to make it sound like some horror movie but sometimes club owners are more concerned with drink sales and not focused on, say, crowd control. And then there’s that double-edged sword of, “I could use a little support here” but then you’re ALSO like, “Men can take care of themselves.” There’s still a long way to go, but it’s fun.

Jim Gaffigan: Well, I can’t really speak for my entire gender.

Reggie Watts: [really long pause]

Jena Friedman: Reggie?

Reggie Watts: Yes.

Jena Friedman: Is it hard to be a man in comedy?

Reggie Watts: It is, because you constantly have to watch your back, you have make sure what people are laughing at are your jokes and not just your nice hips.

When did you decide to become a male comedian?

Eugene Mirman: [Laughing] I can’t handle that uh, that it’s, that —anyway, when I guess when I was eighteen I decided to be a male comedian. Or at seventeen I think I realized that comedy was the kind of job and I was male and so that’s what happened.

Jim Gaffigan: Well, I didn’t decide to become male. I was born male.

Bob Odenkirk: I’ve always been male… and I… just… WHAT?! [Laughing] I always wanted to be a comedian since I… I just did… that is what I did. Yeah, uh… yeah… Since I was a kid. I always just… [Long pause] I didn’t think I had a choice to be come a female comedian so… it was a different time, I didn’t have that option [Laughing].

Reggie Watts: Uh, I was a little nervous about it at first because there’s not a lot of precedent for male comedians. Age sixteen was when I started but I probably did it for realsies when I was thirty years old.

Fred Armisen: [Laughs] I think I was around thirty-two. It wasn’t that much of a decision. I just started doing comedy more and more.

Jon Stewart: [laughs] Um, you know for years I was a boy comedian and I think it was at some point after my bar mitzvah that I decided— actually I don’t think I decided, I think it was just pronounced and anointed. It was at a ceremony--- [beep] HOLY FUCK… Could you hear that?

Jena Friedman: No, what?

Jon Stewart [is driving a car during the interview]: You didn’t hear that? All of the sudden an Amber alert went off on my phone and made a shrieking noise-- apparently there is a gentleman in a silver car in East Orange who is considered armed and dangerous and I have apparently been deputized to go get him.

Jena Friedman: Are you gonna end this interview so you can find a missing child? That would be the best PR move…

Jon Stewart: Here’s how important this interview is for me: You’re just gonna go on a ride along. I’m not going to end it, you’re just going to experience Cops, Stew style [sic]. I can’t believe you didn’t hear that.

Jena Friedman: I love the idea that there’s a B story to this interview [Laughing]

Was it hard to be a male comedian back when you were starting out?

Jon Stewart: [laughs] It’s so interesting that they view it as a sub species. Now to [journalists] somewhat credit, it was actually much harder to be a female comedian when I started, it really was all men. There was Joy Behar, Susie Essman, there were some young comics, Laura Kightlinger, Janeane Garofalo but they were sort of on the vanguard. But if you went to The Comedy Cellar on a Friday or Saturday night, it was mostly 100% male or 90%--

Jena Friedman: So to circle back to my question, was it harder to be a male comedian?

Jon Stewart: [laughs] Right. Yes! Because the competition was fierce! There was only every slot so you had to fight for all of them.

Fred Armisen: It wasn’t that hard. I just didn’t have many expectations. You know, even if I performed to not many people, it was fun for me anyway.

Do you think it has changed for men since you got into the business?

Eugene Mirman: Yeah

Jena Friedman: In what ways?

Eugene Mirman: YouTube.

Reggie Watts: I think men have more to worry about and that’s a good thing. It’s nice to see advancements like that, in my lifetime.

Fred Armisen: I think everything has changed for everybody. Time just does that. But it’s a good thing, things changing.

Patton Oswalt: I think people are coming in with less expectations — they’re not assuming you’re going to talk about tools or cars or home repairs. Men go shopping too!

Jon Stewart: Definitely it has changed for us, when we finally broke through and were allowed in every comedy club… before men were allowed in comedy clubs, it was only men.

Jim Gaffigan: I don’t understand where that question is coming from.

Do you think men can be attractive and funny?

Eugene Mirman: Probably.

Fred Armisen: That’s actually a good question, not that the other ones weren’t good questions [laughs], yes I do... Bob Odenkirk, he’s attractive… I mean, Charlie Chaplin was attractive—

Jena Friedman: [Laughs] Everyone’s attractive to you.

Jim Gaffigan: I think they are two separate things, which really have nothing to do with one another. Funny is [the?] only important thing in stand up. Well, it should be in my opinion.

Jon Stewart: I have not seen it. I think if they were attractive they wouldn’t need to be funny.

Do you think men can be sexy and funny?

Patton Oswalt: I’m not gonna lie and say that a nice shoulder-to-hips ratio doesn’t open some doors, but after that you’d better be able to deliver the material. You’d better be funny. I know a lot of male comedians who were VERY handsome and figured they could coast on that, but then Pepitone is suddenly getting all of the TV gigs. It’s a wakeup call once you hit that stage.

Bob Odenkirk: Actually no. I don’t think comedians can be sexy. I supposed there might be a few who are, only to fetish freaks. I think part of being a comedian is being an underdog… not being cool, or sexy… I’ve always thought you can’t have both, to be funny you have to be making fun of convention. Beauty and sexiness is very often fitting an ideal.

Jena Friedman: These are all questions female comics have been asked so if any are off putting, I’m sorry.

Bob Odenkirk: Tough shit is what you’re saying [laughs].

Do you think it’s more difficult for male comics who are not attractive?

Jim Gaffigan: Wait, are you saying I’m not…

Jon Stewart: [laughs] Yes. It is very, very difficult. That’s why we are out at night. I’m pretty sure that’s why there’s a two-drink minimum, it’s not to loosen people up for the funny, it’s to make us palatable to the eye.

Reggie Watts: It is, 100%. I have a lot of male friends who are not attractive and they have lost out on many gigs, even open mics.

Jena Friedman: Are you being serious?

Reggie Watts: No, [laughs] no, I’m not.

Fred Armisen: I think for male comics who are not attractive, they’ll find their place. And sometimes, they’ll even make jokes about it… and by they I’m not implying that I think I’m attractive— [laughs]

Jena Friedman: [laughs] You’re clearly on your toes by this line of questioning. Which is all I am really trying to achieve—

Fred Armisen: These are great.

Jena Friedman: They’re all real questions.

Fred Armisen: God.

Is it harder to date since you’ve started doing stand up?

Reggie Watts: It is because women are very intimidated.

Jim Gaffigan: Stand up is strange life so it makes traditional or “normal” dating virtually impossible.

Fred Armisen: [laughs] Oh my god.

Jena Friedman: What’s the “oh my god” about?

Fred Armisen: Is it hard to date?! Um, is it hard to date, since I’ve started doing stand up? It’s the same.

Bob Odenkirk: [Pauses then laughs loudly] Well, I’ve been married for 24 years so uh—

Jon Stewart: I’m stunned, are these real questions?

Jena Friedman: Yes.

Jon Stewart: [laughs] It was the only way I could date, sadly… I love that that’s their concern for a female comic is, “You went into comedy, are you prepared to die alone?”

Jena Friedman: It’s a real concern!

Jon Stewart [driving]: By the way, I just let someone go even though I had the right of way and I don’t know if you can capture that type of altruism [in the interview]…

Jena Friedman: For sure!

Jon Stewart: And I’m not even sure I got a wave on it, but that’s fine.

Do you write your own material?

Fred Armisen: [Pause] Yes!

Patton Oswalt: I really do! I guess it’s a compliment when people tell me, “You could totally hang with the lady comics!”

Reggie Watts: [Laughs] Oh my god. Uh. Yes. Most of it. Actually it writes itself.

Jena Friedman: Why did that make you laugh?

Reggie Watts: It’s just like the most, like, I guess backhanded. It’s just so, come on man, Jesus Christ. “Well, we gotta prove women are just as funny as guys are, so just to be sure do you write your own material? We’re hoping it’s yes.” I mean, what the fuck, come on!

Jim Gaffigan: Yes. Well, occasionally I write with my wife.

Jon Stewart: [laughs] I have a team, almost like a construction crew.

Eugene Mirman: Um. Sorry, another call was coming in. I wasn’t stumped by the question [laughs]. The real answer is: yes. I’m trying to think of a joke answer—

Jena Friedman: This is the one question people get the most offended by.

Eugene Mirman: Oh, I’m not offended!

Jena Friedman: Oh, I know, I know! [Laughs]

Eugene Mirman: I just wanted to be like “a penguin writes my material” but I wanted it to be a better thing than that [laughs]. I’ll say that I write my own material but in a week I might email you with a better joke.

Jena Friedman: You can totally do that!

Eugene Mirman: Right, right.

Jena Friedman: I just wanna make you guys feel safe, not like how I was when I was asked these questions.

Eugene Mirman: [laughs] when you did all of these interviews that are on record. Yes, I think the correct answer is I write my own material.

Bob Odenkirk: [Pause] YES! No one else is to blame for how bad my material is, just me.

Jena Friedman: Have you ever been asked that?

Bob Odenkirk: No, never been asked that. It’s ridiculous. Nobody should be asked that after 1972.

Is all of your material about being a dad?

Jim Gaffigan: No.

Jon Stewart: That’s a tough one because you could see that not being viewed through the lens of pure sexism but somebody who actually knew the act and could be like, “Are you just having children to get another 15 minutes?”

Jena Friedman: [Laughing] I feel bad for whoever I asked that question to via email and not via phone call, like Jim Gaffigan, because his interview was via email and I think I offended him!

Jon Stewart: Aw man, that’s funny.

Bob Odenkirk: [Laughing] No, just very little of it.

Eugene Mirman: Um, if I hope to take my comedy to the next level I will stop doing stand up about weird things that have happened to me and I will switch mostly to fatherhood. My comedy is a mix of what happens to me, which now incorporates fatherhood.

Fred Armisen: None of my material is about being a dad. I’m not a dad.

Jena Friedman: I’m sorry I just assumed, since you’re a man that you’re a dad.

Fred Armisen: No.

Do you do any material that isn’t about your gender?

Jim Gaffigan: Yes.

Fred Armisen: [Laughs] Often, yes. I do a lot of material that isn’t about my gender. I might even say that I don’t think any material is about my gender.

Reggie Watts: Uh, yeah. I do a lot of stuff that isn’t about my gender. I think the only way to help equalize the equation is to really move away from calling out the obvious. That’s how I look at it.

Jena Friedman: Do you think I’m calling out the obvious?

Reggie Watts: [laughs] No! Well I think you gotta call out what you’re feeling! But it’s why I never do material about being Black, I mean, you can see me.

Jon Stewart: [laughs] Well, in this patriarchal society, in essence no I don’t because the foundation of all of my material is the authority that I wield.

Jena Friedman: Wow.

What’s it like to work for Jon Stewart?

Jon Stewart: Tedious.

Are you easily offended?

Reggie Watts: No.

Jim Gaffigan: I like to think I’m not easily offended.

Fred Armisen: No, I am not easily offended.

Jon Stewart: [Pause] They asked that to a comic?

Jena Friedman: Yeah

Jon Stewart: Just a question, “Are you easily offended?”

Jena Friedman: Yeah.

Jon Stewart: [Pause] Yup.

Jena Friedman: [laughs] You’re the only one who answered yes!

Jon Stewart: I am easily offended.

Jena Friedman: Thank you for being an ally.

Jon Stewart: I am easily offended. By the way, if you’re in comedy you’re easily offended, just by different things. The whole point of comedy is we take offense to things. Of course we’re easily offended. That’s the craziness about P.C. culture is, we can’t complain about people giving shit to you about something because our entire careers are based on giving people shit about things, we just think it’s the right shit.

Jena Friedman: That’s so vulnerable. No one else wanted to admit that they could be offended. That’s such a feminist gesture.

Jon Stewart: Aw, thank you.

What’s it like to be away from your kids?

Jim Gaffigan: It’s hard. I joke around [about] it being a relief but it’s actually very difficult.

Bob Odenkirk: It sucks, it’s terrible. It’s the hardest part about being in show business for me and a source of great sadness through a chunk of my life.

Do you have help?

Reggie Watts: No, not really.

Fred Armisen: Yes. Collaborators, writers. Yes.

Jena Friedman: I mean in terms of domestic help.

Fred Armisen: I have a handyman who comes around once in a while. I have a housekeeper who comes every week and gardeners… so that would count as domestic help.

Who takes care of your kids when you’re working?

Jim Gaffigan: My wife.

Bob Odenkirk: My wife does. I’ve certainly done my share when she’s working too.

Jena Friedman: It’s so funny because the last time I heard your voice was during the Howard Stern interview and it was so good and nuanced and I’m just reading off a list of questions female comedians have gotten and I feel like such an asshole. Thank you for being my guinea pig because these are so uncomfortable to ask.

Bob Odenkirk: No, I love it. This is a smart idea. You’ve got a good idea here. Keep going.

Jena Friedman: Um, alright [nervously laughs]…

Do you think women should accept Louie CK’s apology?

Bob Odenkirk: Do I think women—am I trying to tell women how I think they should feel? It’s a tough one but there’s no question that his situation is a complicated one but in my mind, I would hope that people would accept his apology over time, because I think he’s genuine in it. Part of the process we are going through, there has to be some place for forgiveness in the world.

Fred Armisen: I make no generalizations. I think every individual has their own personal reaction and decision to make about that.

Jim Gaffigan: Well, I can’t speak for an entire gender or even another individual’s viewpoint on the matter.

Eugene Mirman: [Laughing] Whatever each person feels like is what they should do.

Reggie Watts: [Deep breath] No.

Do you think men should accept Louie ’s apology?

Jon Stewart: [Loudly laughs] For which offense?! [laughs] That’s funny.

What was your personal experience with Louie CK?

John Stewart: More jokes, less penis.

Eugene Mirman: He would do shows at a Chinese restaurant when I lived in the Somerville area 25 years ago when he would record Dr. Katz. So he would come and do sets.

Reggie Watts: My experience is that he’s very much all for himself at the cost of others’ wellbeing.

What’s your work/life balance?

Patton Oswalt: I’m very lucky in that my wife is very supportive, and tries her best to cover the “dad” role when I’m gone. Plus, she’s very understanding, and is so good with the sort of “switching the roles” of me out being the breadwinner.

Jim Gaffigan: It’s ever changing. There is no week or month that is the same.

Bob Odenkirk: 99% work, 1% life. I’m a modern man [laughing].

Reggie Watts: Well, you know, it’s okay. I have to worry about a lot of things, I really fight for my right to be paid less for the same amount of work that I do compared to women, but I enjoy it.

Fred Armisen: I feel like work is part of my every day life. It’s mixed in. It’s not a split thing. It’s all kind of the same.

Eugene Mirman: Normally it’s more life and slightly less work. More just taking care of my son during a pandemic and stand up is currently a dangerous art form.

Jon Stewart: I don’t have one and I’ve never been asked to have one.

But back to Louie…

Jon Stewart: [Laughs] That is a segue worthy of Matt Lauer.

Reggie Watts: Yes, finally.

Eugene Mirman: [Laughs] Go on.

I’m interested to know what degree you think his comedy has changed, and what degree you think the way we have experienced his comedy has changed.

Eugene Mirman: I think with the news that came out it affected people’s perception of his likeability… I do love how many questions you get about Louie. It’s really funny.

Jim Gaffigan: I haven’t seen any of his comedy in years.

Reggie Watts: Oh boy. I don’t think his comedy has changed at all, I think that we all think that he’s kind of a douche bag.

Jon Stewart: Wow. Wow. [Pause] That’s just, who asked that—

Jena Friedman: Isaac Chotiner from The New Yorker. In his defense, he did give me a heads up that he wanted to talk about Louie.

Were you at Late Show with David Letterman when the controversy occurred with him sleeping with female employees?

Jim Gaffigan: I appeared on his show a couple times during that period but it never came up. I don’t know why it would.

Fred Armisen: No I wasn’t. [Pause] What the fuck? What is that? It’s so distant! The whole thing is so distant. “Were you in Norway when that serial killer killed all those people on that little island.” No.

Eugene Mirman: No, I’ve never worked on a late night show—wait were you there?

Jena Friedman: No, but I did work at Letterman, so that is a question that is in the bounds of acceptable.

Eugene Mirman: Meaning that’s a question that you got? But you worked at Letterman for some period?

Jena Friedman: Yes it is, and I did work at Letterman for a year and the thing with the intern happened before I was there and it wasn’t a bad question because it probably did influence me never really meeting him, I just thought it would be funny to ask that question to someone else.

Eugene Mirman: Right, right.

Jon Stewart: [Laughs] I might have been. I was a guest pretty frequently. I may have been there during that time.

There’s Amy Schumer and Lena Dunham, who are outspoken feminists, but who also raise concern about “White feminism.” Is that a concern for you as well?

Reggie Watts: White feminism? Uh, is that a concern for me as well… uh, I… you know, I really don’t think about it [laughing].

Fred Armisen: It’s not… It’s such an impossible question. It’s also unfair to Amy and Lena. How is a person supposed to answer that?

Jena Friedman: Exactly [laughs].

Your fellow comedians like to joke about how you slept your way to fame. How accurate is that criticism?

Jon Stewart: [Laughing] Oh my god! So many suppositions in there that are just brutal! I will say this, for men that would be posed as tongue in cheek for the ludicrousness that that could be a question.

Tell me a joke.

Jim Gaffigan: I’d rather not.

Eugene Mirman: That’s fair uh, that’s a question that interviewers don’t ask me but that I get in general in regular life that always feels unpleasant because stand up is the illusion of a conversation, not a real conversation so I don’t have a jokey joke.

Jena Friedman: That’s a good answer. I think non comics don’t realize what a weird question it is.

Eugene Mirman: Maybe ask Mel Brooks and what he writes in, you can use as my answer.

Jena Friedman: That’s a good joke!

Bob Odenkirk: My DVR is completely full of shows about hoarders.

Jena Friedman: I am sweating asking these questions.

Bob Odenkirk: I don’t mind telling you a joke but I don’t want to tell a reporter a joke [laughs]

Jena Friedman: Oh for sure. I told him that’s the comedian’s equivalent of “show me your tits.”

Bob: Yes. That’s right. It’s true! Well, that is your joke. Jena, that’s the best!

Jena Friedman: We get these questions all the time, so we become— we’re in offensive mode.

Bob Odenkirk: It’s easy for me to answer it as a novelty, the difference is when you’re asked that question, you’re asked to assume so many assumptions ingrained in it that are ridiculous and fucking insane and you don’t get to laugh at them. You almost can’t answer the question. If I answer your question then I am accepting your presuppositions, which are insane and yet come across, are culturally… I mean, do you write your own material is such a weird thing to ask someone after 1972 and the fact that a modern female comic might be asked that is insane.

Jena Friedman: I love that you’re answering these questions with a sincerity that I wasn’t prepared for and I really appreciate it.

Bob Odenkirk: Of course.

Fred Armisen: [Pause]

Jena Friedman: Fred, tell me a joke?

Fred Armisen: [long pause] Um, this is like a form of performance art where my joke is just this silence and these few words, so it’s a sort of an abstract joke.

Jena Friedman: That was funny, did your girlfriend write it?

Fred Armisen: [Laughs] No I came up with it on the spot.

Do you have any jokes before you go?

Jon Stewart [laughs hysterically]: That’s mindboggling.

Jena: Have you ever been asked any of these questions?

Patton Oswalt: I have never been asked anything even REMOTELY like these questions. The fuck is wrong with people?

Eugene Mirman: No, I’m often asked when was I interested in doing comedy? But nobody would ever say “man in comedy.” I think that the way they are phrased, it’s really that gender is being shoe horned into stuff that feels wildly unrelated to the act of comedy. If I go through interviews I am asked a lot of strange stuff, it’s not just gender-y.

Jim Gaffigan: No. I’ve received many “lazy” questions from reporters such as “describe your comedy” or “Do you only do food jokes?” but nothing as flatly insulting as these.

Jon Stewart: There were a couple that I have gotten like, “Tell me a joke?” And the question about work/life balance, but based on them knowing I spend too much time in the office.

Reggie Watts: No, maybe one about being a minority but not really.

Jena: How did it feel to be asked them?

Reggie Watts: Tiresome. Jon Stewart: Demoralizing.

Jim Gaffigan: It was strange. I think it provides insight to the perspective of how female comedians are viewed by entertainment writers and society at large.

Bob Odenkirk: It’s hard to hear these questions and go “who would have asked these questions? That’s insane.” But the truth is a lot of people would ask this and they see the world this way… there’s a lot to make fun of in the world still.

Eugene Mirman: To do an interview that has all of these questions that are not about you feels odd? Can someone be attractive and funny? The answer is obviously yes, it’s at the edge of a question… The irony is people think they are doing something unique but they are doing the opposite.

Fred Armisen: I felt like there was something removed from the whole things. Me as a comedian, this has nothing to do with anything I have ever done. You could be talking to some stranger about any job. I felt like “This person isn’t even interested in comedy.” It’s like a child asking a question, a child who doesn’t understand how the world works. “At a hospital, do you have appointments?” It’s shocking, it’s so funny.

Jena Friedman: Thank you for being so brave. [Laughing] And I’m sorry if any of the questions—

Jon Stewart: You don’t need to be apologetic for any of it. Exposing what’s considered best practices in journalism when it comes to comedians who are women, you don’t need to apologize for putting a light on that.

Jena Friedman: Thank you.

Jon Stewart: The other thing is that you’re not hurting us to get to that point, at all. We’re in the business of saying things and if some of the things we say get push back, the truth is all of the things we say at some level get that and that’s just the business we’re in. I feel your struggle with wanting to make sure everyone is safe. But Jena, you can’t.

Jena Friedman: I just want to make men feel safe [laughs].

Jon Stewart: [laughs] By the way, it doesn’t go unnoticed— [laughing] but do you know what I mean? I just hear it in your voice, you’re doing a smart and funny thing and you’re doing it well and you don’t need to apologize for that.

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