Fresh Air - Comic Jeff Ross on roasting, loss and his epic bar mitzvah

Episode Date: April 7, 2026

Known for his ruthless celebrity roasts, Ross turns inward in his Netflix special, ‘Take a Banana for the Ride,’ which details the loss of his parents and grandfather. The comic spoke with Terry Gross about working at his family’s catering business, his breakthrough ‘Letterman’ set, and living with alopecia. And, upon Terry’s request, he roasts her. To manage podcast ad preferences, review the links below:See pcm.adswizz.com for information about our collection and use of personal data for sponsorship and to manage your podcast sponsorship preferences.NPR Privacy Policy

This is fresh air. I'm Terry Gross. If you're a fan of celebrity roasts, you probably know my guest Jeff Ross as the roast master general. He loves to make people laugh by insulting the guest of honor, as well as the roasters. But his new Netflix comedy special is very personal and autobiographical. It hits lots of emotional notes and reveals a more vulnerable side of him beneath the tough skin that's gotten him through tough times. He talks about his family. His great grandmother founded the popular. New Jersey Catering Hall Clinton Manor, which Ross's father eventually took over. It was known for its weddings and bar mitzvizhs and for the food. One of the people who aspired to have a wedding there was the main character in Judy Blume's 1978 novel Wifey. While Jeff Ross's friends were out having fun, he was cutting brisket for the next catered affair. It was a tight-knit family, but that kind of ended when Jeff was young. His mother was diagnosed with leukemia when he was 12, and died when he was 15. Five years later, his father died of an aneurysm, leaving Jeff and his younger sister orphaned. In his early 20s, he lived with his grandfather and became his caregiver until he died.

If you know what Jeff looks like, you know he's bald. It's not a fashion statement. It's a result of alopecia, a condition in which you lose your hair, including eyebrows and eyelashes. Shortly before he started preparing his one-man Broadway show, in which he talks about all of these things, given a far worse diagnosis that he added to the show, and that was stage three colon cancer. It required surgery and several months of chemo. His new Netflix comedy special is a filmed version of that show, which is called Take a Banana for the Ride. The special begins with clips of him from a couple of roasts, including the now famous or infamous 2024 roast of Tom Brady, which was produced and co-hosted. Here's Jeff Ross.

Snoop. Love you, man, so much. The only person that's inhale more smoked than Snoop is Pete Davidson's dad inside the World Trade Center. Thanks, Pete. Tom, I really wanted you to be our first goat to be roasted because you're an example to future generations that if you work hard, eat right, film the other team's practices, deflate the balls, and have the NFL make new rules just for you.

then you too can be the third most famous guy in a Dunkin' Donuts commercial. Jeff Ross, it's great to have you back on the show, and that stuff is so funny. Terry, thank you. I so enjoyed hearing you ramp this up. I can't even tell you. What a full circle moment for me.

This is my record-breaking third time on. I don't know how many comics have had this privilege, so I'm thrilled. Oh, it's great to have you. So to the extent that you're comfortable, talking about it. How is your health now? My health is 100% thank you for asking. Oh, that's such great news. I just had my chemo port removed. Oh, great, because you still had it on when you were filming the show, the World War Show. So it's really important for people to know that I'm doing okay. I'm

doing better than okay. And don't worry about me, at least right now. I feel very fortunate. And to the people listening who are going through chemo, it's you can do it. You can do it. You can do it. I want to talk now about how you became you. Yeah. So let's start with the catering business. My parents were such veterans of catered affairs, weddings and barmages at various catering halls around like Queens and Brooklyn. Yeah.

So let's start with your grandmother. She founded this successful catering hall in Newark, New Jersey, and then you moved like, the business and your family moved to which part of New Jersey after that? Newark was on Clinton Avenue, was Clinton Manor, and eventually moved to Route 22 in Union, New Jersey, where I work there as a boy and a young man. I want you to describe what the typical bar mitzvah was like when you were working in the kitchen.

You know, I would ride my moped on the, you know, egg turning lane of this highway, you know, 12 months a year to go to my family-owned catering hall where these lavish affairs would happen. So I saw, you know, human nature, people at their most nervous, brides, grooms, mother of the bride, father of the groom, like, you know, you saw people at their most intense. I would watch the bands from a window in the kitchen. You know, I would it's like peak out as a 13, 14, 15 year old working weekends and summers making fruit cup and salads. And, you know, I played high school football, but I had red fingernails from the cherries that

I put on the fruit cups. Oh, Marasino cherries. Everyone thought I was wearing nail polish. And since I was the center, the punt center, they all stared at my hands. So there were a lot of funny crossovers. I worked parking cars there. My grandfather and I ran the parking lot. sometimes. I worked as in the hat check, like taking people's coats as a boy. As a little boy,

I rolled meatballs. I would just sit on a big barrel of salt, metal, you know, canister, and I would roll meatballs for hours. Or in my teens, I would feed the workers. I would make matzabry for 80 people on a Sunday morning. You know, the servers were all Scottish and Irish. There were Haitian There were Hungarian people. There were French people who worked there. So I got a real mix of ethnic humor and different senses of humor. It was a very enriching time for me. I just have to briefly ask you about the food.

Like my parents grew up during the Depression. And their parents were Jewish immigrants from Eastern Europe. So there wasn't a lot of food early in their lives or in their lives. or in their parents' lives. So when they'd go to like a catered wedding or bar mitzvah, they would just like eat and eat. And there's so many stages of food. Like at the catered affairs they'd go to,

there'd be a smorgas board, which would have like sculptures of chopped liver. And like Charmaine was the Chinese dish. There was Swedish meatballs. And Dutch's potatoes. Yes, and some kind of like chicken. and other side dishes and salad, then you first sat down to the meal. And on the really lavish ones, like if you're going to somebody's, you know, catered

affair who had more money, then after that there'd be what was called the Viennese table, which was breakfast. So it was like three meals in one event. And it was, and then everybody would have like a very sore stomach afterwards. So was it like that? Everyone felt like a king when they left. left, you know. Well, I think they were in pain.

Wasn't the Vienn't the table dessert? Halava and ice cream and cake and... Oh, maybe. Maybe it was dessert. But then after that, I remember once there was a breakfast. I mean, and I thought, this is insane. You know, I think we might be finding a direct connection from the kosher catering business to me getting calling cancer.

I think we just figured. it out. And then the band, sometimes the bands were so bad because the parents would hire a band that suited their taste. And so the band would play like lots and lots of chachas and just like songs that the actual bar mitzvah age people were totally uninterested in. But they would play like one or two songs that they thought would like, this is for the kids and they would do like terrible covers of it.

Did you see some really awful bands? I saw the house bands are the ones I remember, and they were always great. Dave Aaron, and before that, my grandfather's band, the Herb Larsen Orchestra, who I played their music in the credits of the Netflix special. It was fun actually, like, finding my grandfather's old jazz albums, and I would play it as people were coming into the Broadway house. So the Niederlander was filled with my Pop Herbs jazz band from the 1950s. 50s. Another connection, Terry, is the catering hall, the building where the Clinton Manor was for all those years was torn down recently. And the weekend they tore it down was the weekend that we built the set into the Niederlander. Wow. Yeah. Beowulf Burritt's beautiful set went up the same weekend that the old building came down. And my family got a real chill from that. But also, you know, it's like a real sign that life goes on. And we've kind of rebuilt the Clinton Manor into a Broadway show. You know, we had a real, like, family pinch me moment of the Clinton Manor, my great Grandma Rosie, this great leader of our family. Maybe the only person on

earth I've ever been jealous of because she worked upstairs. She was a real, like, pioneer in her field. She had this kosher catering hall before women really owned a lot of big businesses in Newark, New Jersey. And her three sons, My two uncles and my grandfather, it was the bandleader. My uncle Murray ran the kitchen. My uncle Albi worked there for a while. We say he cooked the books. That's the joke that I do in the show, how family businesses work.

And she was like the boss of the family. She really kept the family together. She kept everybody fed and employed and happy. Were you brought up religiously or culturally Jewish? Culturally. Bar mitzvahs, all that stuff. I did it, but it was a struggle. What was your bar mitzvah like?

Was it lavish? My bar mitzvah was like something between a Super Bowl halftime show and like something, you know, Saddam Hussein would throw from one of his kids. Like every favor of New Jersey was called in, you know, the best band, the best florist, the best, you know, of everything. It was like my dad, my mom, they really went all out from my bar mitzvah. It's a core memory for me. And, you know, talk about a Viennese table. People are still talking about it.

The desserts, the cheesecake, the bapka. It was, you know, it was a beautiful bar mitzvah. I remember the first three words of my haf Torah. So religion, it was not the focus for us. It was always cultural, like Jewish pride, Jewish strength, Jewish food, Jewish music, Jewish laughter. That was sort of my upbringing. You became the second youngest black belt in America when you were 10.

You were bullied at school, and your mother suggested that you should take. Was it karate, taekwondo? It was taekwondo. She dragged me. I did not want to go. Okay. That's Korean karate. Yeah.

So once you got there, though, did you like it? You must have stuck with it to become a black belt. I immediately loved it. I was terrible. I was punching with my fists upside down. I wasn't coordinated. I, you know, six years old when I started. But quickly, I learned that it was more than just self-defense. Like, it was community. It was role models. I was taught by these Newark detectives. And, you know, I would hear the way they talked about life. You know, they're wives, they're kids. I just learned life through my karate teachers. And I learned discipline. And I, you know, I learned to protect myself. I think that gave me confidence to talk smack for a living later in life.

It was cool. Did you ever use your taekwanda skills to fight bullies in school? I did. I did. It was more like not fight bullies, but defending others against bullies. I didn't like when people got picked on. So sometimes I would step into those kind of messy situations. So you said that learning taekwondo, Korean karate,

helped you talk smack without being worried about getting beaten up for it. I mean, on some level, I am in a dangerous occupation. I'm telling notorious figures. You know, roasting is sometimes dangerous. So when you were 12, your mother was diagnosed with leukemia. She died when you were 15. Were you very close? We were.

We were. What was it like watching her suffer when you were so young and you probably hadn't seen someone suffer like that before? It was hard. It was hard. It was hard to see somebody. so tough, it was so full of laughter, such a positive person, suffer. And it made me realize that life is very unpredictable.

And we were responsible. All of us are responsible for our own happiness. What caregiving responsibilities fill to you? Your father was really busy with the catering business. besides the having to take care of yourself for her you know she wanted to make sure while she was in the hospital and I was my sister and I was playing football I was washing my uniform every night and making my own dinner and just being a good boy we couldn't visit her very often because the hospital was in New York and we lived in New Jersey so I would write her letters and that was a big part of my mission to cheer her up I'd write her funny letters And I found a bunch of them recently. I couldn't find what I wrote to her, but I found the one she wrote back to me. And she's like, all the nurses had a good laugh.

And she's like, you know, had some funny Nazi name that I must have used. I think I wrote my mama letter as a Nazi general at the hospital. And I remember going to visit her one weekend. And she was losing her hair from the chemo. and she was very upset about emotional telling my sister and I that she'd be losing her hair. And I remember hugging her and making Kojak references. And, you know, we're the only kids at school whose mom looks like Kojak. And we had just seen The King and I, my sister and I, and my dad would take us to Broadway shows to cheer us up after the hospital visits.

And the king and I, Eul Brenner, you know, so I made a joke about that, you know, that she would look like Eul Brenner, who was awesome. And bald. And bald. So I take some satisfaction in knowing that I made her laugh because I found the evidence, the letters. You know, how time works, Terry. It's like, you know, you start to go, did this happen? Did I dream this? Did I exaggerate this 20 years ago?

And then when you find, you know, I kept digging. And I found a letter that my dad wrote to me when I graduated high school. It's the only letter he ever wrote to me. And I read that in the show. And there was some debate in my head whether it belonged in the show or not, because we'd kind of moved on from my dad after he kind of dies in my life story. He dies from cocaine from having too much fun. And so I read the letter.

And you really get to, it gives a chance from redemption from my dad. dad for some of the stuff he missed. He apologizes to me if he was out partying too much or if he wasn't, if we didn't talk about my mom much after she died. And I want to inspire dads to be communicative with their kids. And there were a lot of dads with their kids there at the Broadway show this summer. So I'm glad I'm glad I'm reading these letters. There's a part of me that goes, should I be talking about my parents like this when they're not around to laugh along with it?

But I do think the greater mission is to inspire people and give people hope about whatever's going on in their life. This is something I think about a lot. Like, I don't believe in an afterlife or anything. But there's part of me that really thinks the people I've lost in my family. are somehow hearing what I say. And if there's something that they really want kept private, and I tell somebody they know it, you know, like the people who have died, like they know it.

And I know that they're not alive. I don't believe that they're in the room with me. But there's a part of me that really believes they're hearing it. And I wonder if you feel that way when you're on stage. Not in my family. There's no getting offended. I have a bunch of wackos in my family. Like, I remember, oh, God, I don't know how to tell this.

My aunt Don and Uncle Joe lived in Iran and Japan in the 70s. They were teachers. And eventually there was an overthrow in Iran, and they moved back to America with their baby daughter, my cousin Melinda. And I remember, like, the whole family, like, meeting the new baby. And it was such a big deal. They'd flown across the world and they had this new baby that was born over there. And now here it is in this. house in New Jersey. And we're all just admiring, you know, the beautiful Melinda and the baby's

naked. And my dad goes, you know, to his sister, he goes, Donna, she has your blank. And remember my aunt Donna, you know, here I am a little boy hearing my aunt Donna holding this beautiful baby, shrieking laughing. You know, so I saw the sense of humor of my funny family early on and that almost nothing was off limits. We never want to hurt each other. It's all like in good fun. It's all to snap out of sad times or awkward times.

So like humor is so healing. You know, it really is. Well, we need to take another short break here. If you're just joining us, my guest is Jeff Rob. who's known as the Roastmaster General, having hosted, produced many celebrity ross and dished out many insults on those roasts. His new Netflix comedy special

is a filmed version of his autobiographical One Man Broadway show. It's called Take a Banana for the Ride. We'll be back after a short break. I'm Terry Gross, and this is fresh air. When your parents both died, you lived with your sister, and then when she left,

and I think this was when you were still in high school or after college, you moved in with your grandfather and you became his caregiver until he died. What was it like for you to be taking care of him? I know you liked him very much. You were close? Well, that was my, I felt experienced. I understood, you know, a lot had changed. My family was all spread out.

My sister was in college, and here I was a recent college graduate living with my 79-year-old roommate, who happened to be my best friend for my whole life. As hard as it was, it was also kind of great. Yeah, I loved him. Like, we had fun. We ate every meal together. All my friends became his friends. We were both single.

I was 23, and he was 79. And he would meet women at the senior center. I'm the only one that can drive at night. he would say. And that was his big, you know, that's how he would meet these women. And he would just talk about his girlfriends and dates and encounters. And I would talk about mine.

And, you know, we were like almost like brothers by Pop Jack. Like he was a retired construction worker from the Bronx, like a real blue collar, Jewish tough guy, patriotic but cynical. And I was like, like, loved living with him. It didn't feel like a burden until sometimes it just was, you know. He got sicker and sicker. He'd hallucinate.

And I would take him to his doctor appointments every day. And then at night I would try to go into New York. I would take the bus or driving in New York and try to get on stage. And he would always give me a few dollars for the bus and a banana. Take a banana for the ride. That's where the title, the inspiration for the show. comes. To him, it was like a tough guy's way of saying, I love you. I can't go with you, but I'm on this journey with you no matter what. Having had three deaths, your parents and your grandfather

when you were young, and being raised culturally but not religiously Jewish, did you sit Shiva? Shiva is the Jewish tradition for seven days, not doing anything. You sit on a hard bench. If you're seriously observing, you cover all the mirrors because it's no time for vanity, and you just talk with people and cry and laugh about the person who you're grieving. Did you do that? Yes. My mom died slowly and my dad died suddenly. And the one I remember is my dad's Shiva was, it was so absurd that this guy was dead. He was such like a big shot. Every Everyone loved him. He ran this very popular catering hall. He would go down to Atlantic City and gamble and everywhere we went, people knew him because they'd shared their, you know, parties with him. And, you know, Ronnie. Ronnie Lyftchultz. He had a Cadillac. And when he was just suddenly gone, like, my sister and I, who's, you know, a year, 16 months younger than me, it was just like, it was almost funny. Like, how could you? this be? His estate was a complete mess. He had sort of two wills. I burned one, my sister,

because we didn't want our uncle Jerry as our executor because we knew he was not up to it. And so I hired my own, you know, accountant, and that was a total mess. We never collected my dad's life insurance because it was contested by the life insurance company over his smoking, his cigarette smoking. There was no recourse for two teenagers back then. There was no go-fund-mees. You know, you put in whatever fight you could, but we were just like victims of circumstance. And I just didn't want to be a victim.

I wanted to be a winner in life. I wanted to have a positive outlook. I wanted to make the most of my life, because as I... saw, it could end any second. Right. I'm seeing you in such a different light. You know, I'm so glad that you did the show on our showing us this side of yourself. It's like so a kind of complex and deep knowing all that you experienced.

When you went to college, which was in Boston, after having lived your life in New Jersey, did you use that as an opportunity to rethink who you were? were and remake yourself into the person who you wanted to be or thought that you were. You know, college is like a reboot for everybody, right? So some people change their name. They change their look. You know, for me, it was a chance to really be with other creative people. I immediately started working at the college radio station. Eventually became the music director. I was playing in punk rock bands. I had this creative liberation. Were you the guitarist or what? I was a very bad guitarist. I still am. And I was writing, you know, I didn't really understand

comedy yet. It really wasn't until after college, a couple of years that I understood that comedy was what I should be doing. How did you figure that out? I didn't. Someone did it for me. My friend Mark, who I name check in the Netflix show, he was taking in a stand-of-comedy class taught here in New York by a guy named Lee Frank, who was a comic. And he said, I think you'd be good at it, Jeff. You should try it. And I tried it, and I loved it right away.

Not since karate had I felt like a connection to something. I was obsessed where I could do it all day every day. And that was it. I was trying to get on stage three, four times a night if I could. I just wanted to get my hours in, my five-minute increments of just expressing myself, talking about whatever I wanted. It was so cool. Like, it was all, like, mind-boggling to me.

It was punk rock. It was free speech. It was, like, shout it out loud. I didn't understand that I could be a comedian. And I understood that I loved comedians. Like, as a kid, it was like Steve Martin, the Blues Brothers, Eddie Murphy, these rock star comedians. You know, Eddie Murphy in a red leather suit, that was a comedian. I didn't know it was a comedian.

The Blues Brothers were playing music, but they were comedians. Cheech and Chong were playing music and doing sketches, but at the heart of it, they were comedians. I didn't know that word comedians. I thought comedians were, you know, on Johnny Carson, my parents' generation. You know, and I got a lot from that, too. There was like I remember just, you know, listening. I would never watch because it was late, but I remember hearing Buddy Hackett and Don Rickles on the Tonight Show with Johnny Carson.

I would sit at the top of the stairs where my parents couldn't see me, and I would listen. I could hear them laughing at comedians on TV. So I think it rubbed off on me. You knew some of those old-school comics. You knew Buddy Hackett, and you knew Don Rickett. and you knew Don Rickles. You joined the Friars Club when you were how old?

Oh, boy. I was probably in my early 30s, and that was the coolest. I would play poker there with Greg Fitzsimmons and Elon Gold, and they had a poker room, the George Burns poker room where we could order lunch and play poker, and then they had a billiards room,

and then they had a steam room, and a gym, and then they had a dining room where you might see Milton Burrell or Buddy Hackett sitting under their own portrait. I need to reintroduce you again here and take a short break. I love it every time. If you're just joining us, my guest is Jeff Ross. His new Netflix comedy special is a filmed version of his one-man Broadway show,

an autobiographical show called Take a Banana for the Ride. We'll be right back. This is fresh air. So the first time you were on TV, it was the Letterman show. That was my network television debut. No, it was that when he was on. on a 1230 or 1130? He had just gone to 1135. I guess that would have been April 13th, 1995, something like that.

You know, I don't remember many dates, but getting the call to be on Letterman when he had just gone, number one at that prime time slot was a big, big deal in my business. How nervous were you? Couldn't have been more nervous. Here I was this sort of like young, fragile performer. I couldn't get booked as a stand-up on any of the cable shows. It just wasn't clicking. And I auditioned. I was at this festival, and I heard the comedian in the next room, Mark Marin, get a phone call.

You could hear the phones ring back then from room to room. He didn't get it. He auditioned right before me. And then my phone rang a few minutes later. So we were all getting calls from our agents. and managers at the same time, and maybe the Letterman producer, Daniel Kellison, was calling me, and I got it.

And they said, you're going to do it in a couple months. You're going to be on Letterman, and it was just like a life-changing phone call. So I started getting my act together, and I'm in L.A., and boom, somebody canceled. Letterman shows calling. You've got to catch the red eye from L.A. You're coming back to New York,

the Ed Sullivan Theater, tomorrow. So I flew all night. I landed in New York. And there I was in the makeup chair next to Bob Costas and Penn and Teller, and it was so cool. I just barely had time to call my Aunt Donna and my sister and tell them I was going to be on Letterman tonight. And Paul Schaefer and the band played a rock and roll all night and party every day by Kiss, which was my request. And I ran out to my mark in my one good suit that I had just bought for a friend's wedding, luckily. I came out all cylinders firing away.

minutes. I did my seven or eight best jokes. And it was just like, is this for real? They're laughing at everything. It's washing over me. And it just worked. Like the audience just was rooting for me. And I was just sort of on what they call a flow state. So we have a clip of you on the Letterman show. Oh, great. Yeah. So why don't we listen to that? And this was recorded in April of 1995. I was right. Our next guest is a very funny young comedian making his network television debut. Ladies and gentlemen, a nice welcome for Jeffrey Ross. Jeff.

This is one that my dad woke from my mom. It's called Enough with the Bread already. Your smile blooms like a bright summer flower. Your hair flows down like a soft rain shower. Your eyes are like open seas blue from coast to coast. So how come your ass looks like a truck? Enough with the bread. That was a real letter, right?

It was a love poem that my, you know, it was all, no, no, no, they were long gone, and this is sort of my way of taking that pain into something funny. And then I didn't follow a poem. Did you write that or did your father write it? No, I wrote that. Oh, you wrote that? That I wrote that. Because I know your mother was very self-conscious about her weight.

You talk about that in the show. Right. And I think your father really told her to cut down on the bread. Oh, that for sure happened. Okay. And I think my parents would have laughed at that. joke because the next one that I told, I say this is a love poem in rebuttal that my mom wrote back to my dad. It's called Put a shirt on, you're scaring the children.

And it goes from there. I remember running to the comedy cellar to watch it with all the comics on the TV there. And back then it was all answering machine messages. So suddenly, you know, 80, 100 answering machine messages coming through when I get home. It was like, oh my gosh, all that struggle. I think I just got my black belt, or at least my gold belt, my next level of comedy. Like, suddenly I felt like I might not have made the wrong choice. What was the first roast you ever did? And I assume that was at the Friars Club?

It was. It was a roast of Stephen Segal, who had just made Under Siege 2. and Milton Burrell was the host and it was life-changing. I found my Yankee Stadium, Terry, it was the greatest. What did you say? I walked out and there was no YouTube. I had to go to the museum of broadcasting

and research what a roast even was. And I wrote a bunch of jokes, probably too many. And I walked out at the podium. Milton Burl gave me a terrible dismissive intro. I looked at Steven Seagal. I said a lot of you don't know me, but I feel uniquely qualified to be here today because I'm also a shi-a-hactor.

And Stephen Seagall is looking at me. He doesn't quite understand, get it. It was just like you see Milton Burrow and Buddy Hackett cracking up, and I just kind of went. If you're just joining us, my guest is Jeff Ross. His new Netflix comedy special is a filmed version of his one-man Broadway autobiographical show. show, take a banana for the ride. We'll be right back. This is fresh air.

So I want to ask you about the alopecia, which you talk about in your Netflix special. Yeah. So people who know you know that you're bald. And that's because was it, how many years ago was it that you got it? It was probably about a dozen years ago now that it all happened. Alopecia is a condition, as a lot of people know, where your hair falls out. How did you, if you at all did, explained it on stage to people who were already fans and knew you had a head of hair and suddenly you didn't. Did they think it was like a stylish decision? You know, it's a great question. It's something I have barely come to terms with. I had this big bushy fro. I was making jokes about it every night. And then all within a few weeks,

everything fell out. And then if that wasn't weird enough, my eyelashes and my eyebrows. So I just looked so differently, whatever celebrity, if I was going to get noticed, it was all gone. So it was very rattling, emotionally. And I was trying to put, like, makeup on my eyebrows.

I was wearing hats and sunglasses, and I was saying I was doing it for a role. it took a while to accept it and, as I say, kind of channel my inner rock star, in my case, pit bull, I guess, and be okay with how I look and understand that looks aren't everything and it's how you own it and carry yourself. Going bald is one thing, but people thinking that I was sick or weak for some reason, that really bothered me. That went against my grain. Like, it's hard to go out and be the funny guy if everybody thinks you're fragile. Or the confident guy. Yeah.

Like, if you're not confident in yourself, it's hard to project the confidence on stage. Unless you're acting about your own neuroses and not being confident. Right. And it wasn't. And it was making fun of people. And now suddenly I looked kind of off. So how did you break the news that it was really like a condition? I never outwardly said it until a couple of years later when Chris Rock got hit at the Oscars.

Oh, yeah. What was your take on that? Because you had alopecia, and that's what Jada Pinkett Smith has. And, you know, Chris Rock made a joke that was a reference to her being bald. And then Will Smith went on stage and socked Chris Rock. You know, it devastated me. And I wasn't the one getting hit. I was the one watching from a hotel room in Atlanta. And my girlfriend was like, oh, are they doing a bit? And I shook my head and I started like almost tearing up.

I knew it wasn't a bit. I knew Chris wouldn't do a bit like that. I'd worked with Chris for years. I understood that Will Smith snapped right away and hit Chris Rock, who handled it like a man, like a grown-up. And he went on with the show. And like everything about it hurt me. Will Smith was slapping comedy.

And Chris was taking that hit for all the outspoken, funny truth tellers. He said, but that's the thing that, first of all, the Oscars have become a ross. If you're going, especially if you're nominated, you should expect that there's going to be a dig someplace. In this case, it was, you know, his wife and not himself for Will Smith. But it's also saying that saying that your wife is bald and referring to the fact that she has alopecia is an incredible insult. And you had that condition yourself. So were you insulted by that joke? Or were you more insulted by Will Smith for punching back after that joke?

I was upset for everyone who has alopecia. The Smiths, if they had laughed about it, they would have normalized the condition for kids. They would have seen this most beautiful person on the Oscars with a bald head laughing, normalizing it, taking the stigma away. So that's the first time you talked about it publicly? Yeah.

After hiding it for years, it just suddenly it burst out of me that I wanted all the kids. kids with alopecia. And I know losing your hair for a woman is like, I can't put myself in those shoes, but I also was sort of thrown off and traumatized by losing all my hair in a few days. So I get it. I get why someone would be sensitive. But I also go, well, you're going to be a star. Then you've got to act like a star. And you got to laugh it off. So many of your friends are comedians. And three of them died within like, Eight months of each other.

Yeah. Gilbert Godfrey, Norm MacDonald, Bob Sagitt. You were close to all of them. So you had to deal with a lot of grief at the same time. And grief just seems to be a recurring theme in this interview in spite of, you know, how funny you can be. So here's something. I don't know if you did eulogies for them. But I imagine if you did do eulogies, you'd want them to be funny in honor of their ability.

to be funny. But that means that you have to write a set while you're grieving. So how did you handle that? Well, in Bob's case, Bob died suddenly. So I was angry. My eulogy was angry. And I was sticking up for his wife, Kelly, who really got a raw deal by losing him after only a year or two of marriage.

They really love each other. And I was angry at that one. So to answer your question, I wasn't particularly funny with the sudden death of Bob Sagitt. I spoke from the heart, as they say, but I can't say I was trying to be funny. There was John Stamos and Dave Cooillet and Dave Chappelle and all the funny people. There was definitely some laughs when we lost Bob, but I wasn't there yet. with Gilbert, Gilbert had been suffering. And so when someone's suffering, there's always, you know, you kind of get a heads up.

And when they finally do die, chances are there's some little relief there. And that's where comedy grows in the relief of tension. So when Dara asked me to speak at the funeral, I was guns ablaze and I was ready for that. I was so ready to give Gilbert the kind of send-off that he deserved, which was tasteless. You know, and Gilbert's crazy bawdy, over the top, Friars Club, No Holds Bard, bordering on illegal comedy. So we have to wrap up soon, I regret to say, but I have a request. Anything. Okay.

You might be sorry that you said yes. Here's what I'd like you to do. I want you now to roast me and go hard. You've listened to the show so you know something about the show and about me. And then I, in turn, will let you know how it made me feel. Oh, wow. On a scale from really grateful for the hilarity to I will be self-conscious for the rest of my life. And if I really hate it, I can insist that we edit it out.

Terry Gross Terry Gross has been around so long She interviewed Ed Sullivan I wish I did Terry Gross A barely living legend That's great Well it's been

A pleasure to talk with you again Really always, always enjoy this. You always find something in me that I didn't know was there. Jeff Ross's new comedy special, Take a Banana for the Ride, is streaming on Netflix. To keep up with what's on the show and get highlights of our interviews, follow us on Instagram at NPR Fresh Air. Fresh Air's executive producer is Sam Brigger.

Our technical director and engineer is Audrey Bentham. Our interviews and reviews are produced and edited by Phyllis Meyer, Anne-Marie Boldenado, Lauren Crenzel, Teresa Madden, Monique Nazareth, Thea Chalner, Susan Yucundi, Anna Bauman, and Nico Gonzalez Whistler. Our digital media producer is Molly C.V. Nesper. Roberta Shorak directs the show. Our co-host is Tanya Mosley. I'm Terry Gross.