I spent a lot of time in the late '80s with Roseanne Barr, trying to craft a stand-up act that wasn't just about raising her family and growing up poor, but about what it was like to now be rich and megafamous. It always felt odd to me, as a 22-year-old guy without a ton of life experience, to be writing jokes for an ass-kicking middle-aged woman who happened to have multiple personalities. I used to force her to sit with me and tell me her life story, so I could try to get in her head. The depth of her experience and imagination was astonishing.

This was happening at the absolute height of Roseanne-mania; it was the number one show on television year after year after year. Many people only remember the drama that surrounded her at the time, but I believe that Roseanne was one of the most influential shows ever on TV. Because it reflected the real lives of working-class people and their daily dramas. Because it managed to be riotously funny while also exploring deep truths about how people were living in America at the time—and still are today. It took an enormous amount of courage and madness to make that happen.

And I've known Sarah Silverman since she moved to California to do stand-up when she was 21 years old. Back then she was the young, hilarious girl who was from the same town in New Hampshire as my friend and roommate, Adam Sandler. That always seemed so weird to me, the idea that two brilliantly funny people could come from the same small town.

Last year I interviewed Roseanne and Sarah for this book. They both are legends who have changed the face of comedy.

On Fortune

Roseanne: I have horrible stage fright— you know how you go through the bi-polar stage fright thing? Then you go on drugs to get over the stage fright and perform, but then you're not funny at all.

Judd: Were you always scared when you did stand-up, to the point where you felt like you needed to be medicated?

Roseanne: No, it was only after The Roseanne Show that it felt like that. I'd go on, and I'd want to do edgy material, and the audience would be like, "Where's Dan?" [Meaning John Goodman, who played her husband on Roseanne.] I was like, "Where's a gun so I can blow my fucking brains out all over this stage?"

Judd: Is that the worst part of success— that it defines who you are and what you do? If you succeed in one area, people think you should stay in that area.

Roseanne: They don't even know who I am. They think I'm Roseanne Conner. It's like, "You're not a writer. You're not even a comedian. You're Roseanne." And then I was like, This is freaky because I can't get another job ever. And I wanted to work. I see other comics going through the same shit. Once you make it, it's like, well, you're not, like, hungry or whatever. What the fuck am I supposed to talk about now? My maid? And everybody's like, "You're fucking rich," but they don't get it. They don't get that you have to fucking do it. It's not about if you're rich or not. Because it's what you love. You have to do it because that's the only thing you know how to do.

Judd: And it keeps you sane, but it also creates all—

Roseanne: All the problems. But then it's so worth it when you're getting those laughs. It's like, This is what I do, what I love. It's the whole fucking reason I'm alive.

On Fame

Sarah: I'm so much more famous than I am financially successful. I mean, I live in a three-room apartment. I mostly make free videos on my couch. But I am fine.

Judd: Is it because, creatively, you've done what you've wanted to do?

Sarah: I've always kept my overhead low so I could do whatever I want. I think of myself as lazy with spurts of getting a lot done. I find myself rooting against things sometimes because I get excited at the thought of a clean slate.

Being Broke

Judd: I think about that, too. Did I have a different point of view when I was broke?

Roseanne: Define broke.

Judd: Well, I shared an apartment with Adam Sandler, and the rent was $425 a month, and I was just trying to make enough money to eat and go to the Improv.

Roseanne: How old were you then?

Judd: Twenty-two, twenty-three.

Roseanne: What did you guys do to make each other laugh—or were you just depressed all the time?

My Dad Made Me This Way

Sarah: My dad taught me swears when I was a toddler, and I saw, at a really early age, that if I shocked people, I would get approval, and it made my arms itch with glee. I got addicted to it. It became this source of power in a totally powerless life.

Judd: Did your dad get a kick out of it?

Sarah: He thought it was funny to teach his three-year-old daughter swears. His dream was to be a writer—and he wrote all these books that he self-published when he retired—but he owned a store called Crazy Sophie's Factory Outlet. And he did his own commercials. I have a bunch of them—they're amazing. He has such a thick New England accent. You can't understand a thing he's saying. He's like, "When I see the prices at the mall, I just want to vomit! Hey, I'm Crazy Donald!" He was Crazy Donald, like Crazy Eddie, only in New Hampshire.

I never consciously set out to talk about taboos or anything like that. That was just what the household I grew up in was like. There wasn't a sense of, like, "Maybe let's not say that in front of the kids." It was all out there, you know, and I didn't know better. I mean, honestly, a lot of the human etiquette I learned in life I learned from, like, thank-you notes and dating Jimmy Kimmel. I have great parents, and they both taught me great things, but my formative years were boundaryless.

Judd: But was there a core of morality to it?

Sarah: Oh yeah, definitely. We had no religion at all, but we were Jews in New Hampshire, and my sister—who is now a rabbi—said it best: We were, like, the only Jews in Bedford, New Hampshire, as well as the only Democrats, so we just kind of associated those two things together. My dad raised us to believe that paying taxes is an honor.

Judd: How does your sister talk about Judaism?

Sarah: It's funny because sometimes I'll get cunty with her, and I'll be like, "Oh, so you believe there's a man in the sky?" And she'll go, "Well, I like to live my life as though there is one." And I'm just like, "Oh, you're beautiful."

Judd: I wish I could convince myself to believe the way your sister believes because I'm so exhausted from not believing.

Sarah: I actually don't think that she believes in God, necessarily. I think she just loves the ritual of religion and finding meaning in every little thing. She loves living her life that way.

Judd: She doesn't believe in a God that is actively involved in people's lives, making choices?

Sarah: She doesn't believe that God is rooting for the Giants and not the Patriots. She's not fucking ridiculous.

My Dad and Judaism Made Me This Way

Judd: Did people in Salt Lake know you were Jewish?

Roseanne: They knew. Like, when I was three, I fell and I got Bell's palsy in my face. My mom said the first day she called the rabbi, and he said a prayer for me but nothing happened. The second day she called the Mormons, and they said a prayer for me and my face was healed, so my whole life was going around as a Jew who was giving talks in Mormon churches about being healed by the Mormons.

I used to play Barbies with my Mormon neighbor friend; it was always, "Oh, we're going to go on a date. Ken's taking us out, and we're going with Ken on a date." And I was like, "We're parachuting behind enemy lines to save the Jews." That's how I played Barbies. I was told when I was a girl that every Jewish woman has to have five children to replace three fifths of our people that were killed. That's how I was raised.

Judd: Wow.

Roseanne: In an apartment building with survivors from concentration camps.

Judd: Parents don't realize that when they teach you about the Holocaust too early, it ruins you for life.

Roseanne: It ruined me for life. I remember the exact moment well—I was, like, three, and they had the TV on, and they were of course enjoying the Eichmann trial. When they weren't talking about Eichmann, they were talking about babies on meat hooks. They used to say it in front of me, and I was like, I don't want to be on this fucking planet. This ain't for me. Fuck it. And I went in the bathroom in my grandma's house. There was this black button on the door, and I turned it. I had to stretch real hard to turn that lock. So then they were all like, "She's locked herself in the bathroom," and then it was, like, all this screaming. The only time they talked to me was to tell me that the Nazis used to shoot little girls right through the head in front of their parents. That's how they talked to me. Other than that, it was like, "Pick that up."

My dad was a big fan of comedy. He wanted to be a stand-up. He loved Lenny [Bruce]. He also loved Lord Buckley and jazz and stuff. He was a hipster. My parents were kind of beatnik-y, you know, for Salt Lake City. But my humor, I think, came from wanting to disarm people before they hit me. My family were hitters. If you made them laugh, they didn't hit you. My dad wouldn't hit me if I got him with humor right between the eyes.

Judd: What age were you when he would hit you?

Roseanne: Always.

Judd: The thing that ruined your life makes you good at your work. And then you get rewarded at work, so you don't bother to fix it in your life.

Roseanne: I don't know about that. My shrink says, "Don't say you're funny because of abuse; it's in spite of." But my whole thing is, like, I've had a severe mental illness my whole life. A devastating, dissociative identity disorder—MPD, it used to be called. I had to heal from that, and that was like 15 years of intense daily therapy. I look back, and it's fucking crazy. It's nothing you can explain to people. You can't explain to people waking up in a mental institution in Dallas, Texas, with a shrink screaming in your face, "You don't have a penis!"

Judd: Were you high school age?

Roseanne: No, I was in my forties. It's real deep mental illness shit, man. But I got over it. Not over it, but I live with it.

The Long Road to Making It

Judd: So you're a housewife, and it's floating around the back of your head somewhere that it would be great to do this?

Roseanne: I always knew since I was three. When I was little, that was one thing that I was told in a vision: I was going to have my own show when I grew up. And it's going to be funny.

Judd: So in your head, you knew it was going to happen, and then you're having kids. At some point, you have to make the move to do it. What was the trigger?

Roseanne: I was a cocktail waitress, and I got tips because I made them laugh, plus you had to have half your ass hanging out. I made them laugh, so they'd give me big tips, and this one guy said, "Hey, you're so funny, you should go down to this comedy club downtown." And I was like BONG, BONG, BONG, BONG. So I go down there and I watch all the comics. And I went home to write my five minutes of material—and then I just kept perfecting it. That took a fucking year.

Judd: That's incredible.

Roseanne: It was almost a year, and then I went down there and did my five minutes. I look back on it now, and I'm like, It was pretty ballsy that I said the things I said. They immediately banned me and said, "Don't ever come back here."

Judd: Do you remember what was in the five minutes?

Roseanne: I made fun of male comics. I was very political.

Judd: Did you talk about being a housewife, also?

Roseanne: No, it was radical feminist politics. When I was little, my mom used to read this book, Fascinating Womanhood. There was a character who would tell you how to get your husband to buy you a blender and shit. And it disgusted me that my mom and her friends were like that, so that's kind of why I became a feminist. Me and my sister were eating eggs one day, and I was like, Fuck—it just came in my head—one of those things that didn't have nothing to do with me. It's like: domestic goddess. And I went, Oh fuck, that's my door. I just tailored it for a while and, you know, they let me [back] on. They liked that act. Because I finally found my voice. I went to every kind of club to work it too. I had to go to, like, the Episcopalian church and jazz clubs and punk clubs and biker bars. I remember performing on a punk stage with no mic in the middle of a mosh pit. My act was called "How to Be a Domestic Goddess."

Judd: I used to scream at everybody at the beginning of my career. I'd get really emotional. I'd project all my issues about my parents and safety onto the executives, so every conversation where they gave a note was life or death and you don't love me. You don't get me. It took me a very—a very long time to understand that I need to find people who like what I do, who get what I do. I need to find people who I respect so I can respect them, and they'll like being respected so they'll respect me, and that's like a marriage. But early in my career, you'd get bad notes from someone who didn't appreciate what you were doing, and you would resist them. I would fight and we would always get canceled.

Roseanne: I'm glad to see people are taking more control of their product these days, but back then it was like, whoa, they had to humiliate and belittle people who had talent.

Judd: That's how they controlled things.

Roseanne: It's a pimp mentality.

Judd: How did you take control of your show?

Roseanne: I'd be standing there during the filming, crying. I got a woman manager after every fucking guy who would say the same shit: "Shut up and take it, you're getting paid." So I got, like, Diane Keaton's manager, and she was very connected; she had power. And she was like, "Your star is in tears on this comedy. Do you even notice that at all?" She hooked me up with the lawyer Barry Hirsch. There was one big day on set where I was sitting on the bed, and the director and the producer were like, "Say the line as written." And I was like, "I'm not going to say the line as written," because Barry Hirsch had told me you can say, "I'd like a new line, please." It's a Guild thing. They were like, "You're not going to get it." But then their lawyers would tell them, "You can't force somebody to say a line." So Barry gave me the language to say, "I'd like a line change, please." And it ended up they made me do it for six hours, and then they came back with some legal shit on the loudspeaker with the cameras on. And then that shit gets back to the network, and they're like, "Look what a pain in the ass she is. She needs to go." So they asked all the cast if they'd do the show without me, and John Goodman said no. If he had said yes like a lot of other fucking people in show business, I would have been off there in a heartbeat. And I was like, I made it for this? All this way to have my fucking act stolen and be beaten down and disrespected?

Judd: And then it aired and the ratings were—

Roseanne: Number one.

Judd: Then you had the moment where you're like, "Okay, now here's how we're going to do it."

Roseanne: It was that voice that I always have with me. I said, "Either he goes..." and they knew. So they go, "Well, he'll go, but he's not going until [episode] 13." So that was seven more [episodes]. And I'm like, Oh, how am I going to fucking make it through that? And it was tough, but that voice came in and it's like, Make a list of everybody who you're going to fire the minute you're at [episode] 14. I hung it on my door. I still have it. I said, "These people will not be here next year," and it was big, so whoever walked by would see it. And they were all gone the next year, including the network president.

Judd: If you watch the arcs of so many comedians, at some point, they just become themselves.

Roseanne: That's exactly it.

Judd: And something amazing happens. Like everyone's looking for their angle, looking for their angle, and then they just—they become powerful.

Roseanne: You synthesize it all. You integrate it. I don't want to be ordinary. I'm willing to do the work. I'm willing to suffer the indignities of comedy because I want to be great. I don't want to just be good. I want to be great.

Sometimes the Long Road Is Odyssean

Judd: Seinfeld said he sits and writes for two hours every single day.

Sarah: Seinfeld and Chris Rock, they're just that incredible combination of funny and not lazy, which is very rare and special and completely failure-proof. I remember before I did my HBO special, Chris screamed at me—in a loving way, but still. He was like, "You need to do 200 shows in a row and a month straight on the road before you even think about recording a special!" And I had literally booked two weeks on the road and then went right into the recording. It put me in a panic, but it also made me work harder and made me realize that everyone works differently, and that's okay. I definitely learned to embrace the quiet moments onstage from Garry Shandling—relaxing and not fighting with the crowd, not raising your voice, not ever trying to win them over. I remember the very first time Louis [C.K.] saw me. I was just starting, and I had this affectation where I would pull the mic away from my mouth. And he was like, "You shouldn't do that. It looks weird, and it's a bad habit to get into." And so I stopped.

Judd: What is it like, at this point in your career, to look back on what all these people you came up with have accomplished?

Sarah: You know, everyone's got their own velocity, and there's no real time frame with comedy. Louis has been brilliant for 30 years, but it has been so exciting to see, these past five years, the world getting Louis fever. On the flip side—so many times I will find myself talking to someone, "No, no, you don't understand—he was the king," and people only see a guy washed up, with no place to live, who can't get his shit together. It's so frustrating. Like I said about Seinfeld and Chris Rock, they're a great combination of brilliance and hard work. [But] there are people who are brilliant and don't work hard, and there are people who are brilliant and sabotage themselves. Every once in a while, you forget there's nothing you can do about it, so you scramble, trying to get something going for them, and then you come to the realization that they'll never let it happen.

Judd: And you end up with survivor's guilt.

Sarah: It's awful. Even the cruise ships don't want them anymore. Comedy is like alcoholism. You're surrounded by people who are getting high all day, fucking around, and just being comics—and time passes, you know?

Judd: None of us have any other skill to fall back on.

Sarah: Yeah, exactly.

This article originally appeared in the July 2015 issue of ELLE.

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