Best Of: Arsenio Hall / Jeff Ross

Summary

Fresh Air Weekend: Best Of – Arsenio Hall & Jeff Ross

Host: Tonya Mosley & Terry Gross
Broadcast: April 11, 2026

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Episode Overview

This "Best Of" edition of Fresh Air Weekend features two revealing interviews:

• Arsenio Hall discusses his pioneering late-night talk show, the challenges of straddling cultural expectations, and his new memoir, Arsenio.
• Jeff Ross, famed comedian and roastmaster, opens up about the pain and humor woven into his life, as captured in his deeply personal Netflix special Take a Banana for the Ride.

Both segments explore personal vulnerability, resilience, and the power of humor to bridge cultural divides and process grief.

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Arsenio Hall: Late-Night Legacy, Identity, and New Memoir

Host: Tonya Mosley
Segment Start: [02:33]

Dreaming Beyond Carson

• Hall grew up in Cleveland watching The Tonight Show but aspired to create a show that showcased talent underrepresented in mainstream media.
  • "I wanted to do this show that didn’t exist when I was a kid... I found Bruno Mars and put him on the show when he was 2ft tall. I wanted those things that Johnny [Carson] didn’t do." (Arsenio Hall, [00:28], [06:54])

Breaking Barriers & Facing Backlash

• The Arsenio Hall Show was hip, brash, culturally resonant, and syndicated on nearly 200 stations at its peak ([03:33]).
• Hall’s platform hosted signature pop culture moments, like:
  • Magic Johnson discussing his HIV diagnosis.
  • Bill Clinton’s iconic sax performance, pivotal to his '92 campaign.
  • Addressing racial unrest after the Rodney King verdict.

The Complexity of Representation

• Hall quit the show at his zenith—not canceled as often assumed.
  • "White audiences thought the show was too black, and black audiences thought it wasn’t black enough. And it wore him down in ways he's never told fully until now." (Tonya Moseley, [03:33])

On Feeling "Insatiably Black and Profoundly Alone"

• Hall describes the isolation of never being able to satisfy divergent audience demands.
  • “I’m being told by the black community it ain’t black enough. I’m being told by the Paramount executives it ain’t white enough. And now the gay community is going to attack me during the show… You’re going to blame me for something that is absolutely not true.” (Arsenio Hall, [10:55])
  • “It’s hard being the first black anything in late night.” (Arsenio Hall, [10:55])

Confronting Activist Criticism (Queer Nation Incident)

• Activists disrupted a monologue, demanding more openly gay guests. Hall’s response was personal and frustrated.
  • Notable Quote: "This is my show, man. You think I haven’t had somebody on the show because they're gay? ... I’m black, man. I’m the biggest minority you know about." ([09:34])
  • Hall later reflects: “My staff was gay. Many of my guests were gay. But it was at a time when you didn’t always know it… It wasn’t my job to introduce a singer that way.” ([10:53])

Creating a Welcoming Stage for Black Artists

• Hall’s environment allowed Black celebrities to relax and show rarely-seen sides of themselves, leading to what Mosley calls "black boy joy."
  • Example: Heartfelt, candid interview with Tupac about authenticity, violence, and success.
    • Notable Quote: “[On rap] All I’m doing is showing you and telling you, you know what I’m saying? Why get mad at the brother that bring you the news? Get mad at the person that’s making it happen.” (Tupac Shakur, [15:47])
    • Hall: “Back then, we didn’t have the Internet… We had the Blackbird. That was me. I was the place you come and talk and air out your grievances and say what’s on your mind.” ([17:25])

Navigating Early Ambitions and Family Influence

• First hosted a mock talk show in his basement at age 12; was drawn to stand-up by the thrill of making people laugh ([20:19]).
• His preacher father’s powerful oratory spurred Hall’s own performance style, despite his father’s skepticism toward showbiz as “the devil’s business” ([21:43]).
  • Notable Quote: “It was like a drug that I chased the rest of my life. And I'm still chasing. I love the laugh.” (Arsenio Hall, [21:43])

Vulnerability & Purpose

• Hall reflects on needing his father’s approval and how much of his drive was to make him proud ([23:16]).
• Final thoughts stress the importance of authenticity and the challenge of forging a new path for underrepresented voices.

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Jeff Ross: Laughter from Loss, Family, and Finding Healing Through Comedy

Host: Terry Gross
Segment Start: [24:31]

The Persona Behind the Roastmaster

• Famed for celebrity roasts, Ross shows vulnerability and depth in Take a Banana for the Ride, shaped by loss, illness, and family history ([24:31]).
  • Roast samples include signature biting wit:
    • Notable Quote: “The only person that’s inhaled more smoke than Snoop is Pete Davidson’s dad inside the World Trade Center.” (Jeff Ross, [26:28])
    • Of Tom Brady: “...then you too can be the third most famous guy in a Dunkin Donuts commercial.” ([26:28])

Family Roots in Kosher Catering

• Ross grew up in the family-run Clinton Manor—a New Jersey Jewish catering institution—working every job from parking cars to making salads ([28:36]).
  • “I played high school football, but I had red fingernails from the cherries that I put on the fruit cups.” (Jeff Ross, [29:44])

Food and Cultural Identity

• Bar mitzvahs were extravagant, humor and food inseparable from Jewish-American life.
  • “My bar mitzvah was like something between a Super Bowl halftime show and, like, something Saddam Hussein would throw for one of his kids.” ([34:21])
  • “Jewish pride, Jewish strength, Jewish food, Jewish music, Jewish laughter. That was sort of my upbringing.” ([34:21])

Loss and Letter Writing: Mother’s Battle with Leukemia

• His mother died when he was 15, his father at 20, leaving him and his sister orphans. Ross emphasized humor as a lifeline ([35:19]).
  • “I’d write her funny letters, and I found a bunch of them recently… I take some satisfaction in knowing that I made her laugh because I found the evidence, the letters.” ([36:16], [37:16])
  • Used humor to comfort his mother during chemo-induced hair loss, comparing her to Kojak and Yul Brynner (bald icons).

The Weight and Healing of Grief

• Ross’s comedy is deeply shaped by loss, serving also as a vehicle for family redemption and broader inspiration:
  • “I wanted 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.” ([38:00])

Caregiving, Grandparents, and the Banana

• After college, Ross lived with and cared for his grandfather, “Pop Jack”—the “best friend for my whole life” ([41:59]).
  • The show’s title comes from Pop Jack’s farewell: “Take a banana for the ride,” his way of saying “I love you.”
  • “We were both single… and he would just talk about his girlfriends and dates and encounters, and I would talk about mine. We were like almost like brothers.” ([41:59])

Shiva, Legacy, and the Urge Not to Be a Victim

• Ross recounted the absurdity and chaos of his father’s shiva and estate, underscoring grit and a refusal to be “a victim” ([44:19]).

Finding Comedy and the Influence of Jewish Legends

• Initially unaware of his comedic destiny, found it via a friend’s encouragement.
  • “Not since karate had I felt like a connection to something. I was obsessed…” ([47:26])
• Ross’s identity shaped by exposure to both old-school and punk comedy (Steve Martin, Buddy Hackett, Don Rickles) ([48:20]).
• The Friars Club was formative—comedy as tradition and brotherhood ([49:20]).

Closing Roast and Emotional Reflection

• Terry asks to be roasted; Ross obliges:
  • “Terry Gross has been around so long, she interviewed Ed Sullivan… a barely living legend.” ([50:34])
• Ross: “You always find something in me that I didn’t know was there.” ([51:03])

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Notable Quotes & Moments

• Arsenio Hall on Identity:
  • "To be 100% yourself and still that self be rejected..." (Tonya Moseley, [04:56])
• Tupac Shakur on Truth in Rap:
  • "Why get mad at the brother that bring you the news? Get mad at the person that's making it happen." (Tupac, [15:47])
• Jeff Ross on Family Humor:
  • “In my family, there’s no getting offended. … Humor is so healing, you know, it really is.” ([41:33])
• Jeff Ross on Artistic Purpose:
  • “I didn’t want to be a victim. I wanted to be a winner in life. I wanted to have a positive outlook.” ([44:19])

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Key Timestamps

| Topic/Segment | Timestamp | |---------------------------------------------|---------------| | Introduction to Arsenio Hall | 00:16 – 04:53 | | Arsenio on show creation & barriers | 04:53 – 12:05 | | Queer Nation heckling incident | 09:34 – 11:55 | | Black artists & "Black boy joy" | 13:21 – 19:54 | | Arsenio's family & legacy | 19:54 – 24:20 | | Introduction to Jeff Ross | 24:31 – 28:05 | | Jeff Ross’s family, bar mitzvah | 28:05 – 34:19 | | Jeff on loss and caregiving | 35:19 – 41:59 | | Bananas, Pop Jack, origin of show title | 41:59 – 43:48 | | Shiva and not being a victim | 43:48 – 46:03 | | Discovering comedy, Friars Club | 46:03 – 49:56 | | Jeff Ross roasts Terry Gross | 50:02 – 51:10 |

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Tone & Takeaway

The episode was candid, warm, and probing—balancing humor with raw honesty. Both Arsenio Hall and Jeff Ross shared how their upbringings, challenges, and the difficulties of representing underrepresented communities or coping with family tragedy shaped them as artists and human beings. Listeners are left with a more nuanced perspective of each man's journey, and the enduring power of laughter and vulnerability to break barriers and heal.

Transcript

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[Tonya Moseley]

From WHYY in Philadelphia, this is FRESH AIR weekend. I'm Tonya Moseley. Today, Arsenio Hall. He grew up in Cleveland dreaming of being the next Johnny Carson. Kind of.

[Arsenio Hall]

I wanted to do this show that didn't exist when I was a kid and I knew the talent was out there. You know, I found Bruno Mars and put him on the show when he was 2ft tall. I wanted those things that Johnny didn't do.

[Tonya Moseley]

And we hear from Jeff Ross, comedian, producer and the man behind some of the most savage celebrity roasts on television. But before all of that, he he was a kid growing up in his family's kosher catering hall in New Jersey serving weddings and bar mitzvahs, one of which was his own.

[Jeff Ross]

My bar mitzvah was like something between a Super bowl halftime show and like something Saddam Hussein would throw for one of his kids.

[Tonya Moseley]

He gets personal and vulnerable in his new Netflix comedy special, take a Banana for the Ride that's coming up on FRESH AIR Weekend.

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[Tonya Moseley]

This is FRESH AIR weekend. I'm Tonya Moseley. That's how America was welcomed into the party that was known as the Arsenio Hall Show. His name stretched out the way his mother used to call him into the house when he was a kid growing up in Cleveland. During its run in the late 80s and early 90s, Time magazine called Arsenio hip, brash, and the new generation. And some of the most important moments in American culture happened on Arsenio's couch. Magic Johnson chose the show as the first place to speak after announcing his HIV diagnosis. When Los Angeles burned after the Rodney King verdict, executives wanted the show to go dark. But Arsenio went on anyway. And one night, a charming governor from Arkansas running for president showed up with a saxophone. That appearance would go on to be credited as a turning point in the 92 presidential election, strengthening Clinton's hold on young and black voters who helped carry Clinton to the White House. I was a teenager in Detroit, staying up past my bedtime to watch, and I was not alone. At its peak, the Arsenio hall show was syndicated on nearly 200 stations, running second in the late night ratings to Arsenio's idol, Johnny Carson, and an unthinkable feat at the time. And then, just like that, poof, the show was gone. But here's what I never knew until I read Arsenio's new memoir. The show wasn't canceled. Arsenio quit walking away from a dream he'd been rehearsing since he was 12 years old. The reasons were distinctly American. White audiences thought the show was too black, and black audiences thought it wasn't black enough. And it wore him down in ways he's never told fully until now. His new memoir is simply called Arsenio and Arsenio Hall. Welcome to FRESH air.

[Arsenio Hall]

Well, thank you very much. Wow, what an intro.

[Tonya Moseley]

Oh, Arsenio, you know, you have talked about the decision to leave the show before, but this book, it really names things I haven't seen you name before. You say this thing that was really poignant to me. You said you felt insatiably black and profoundly alone. Take me inside of that. To be 100% yourself and still that self be rejected.

[Arsenio Hall]

Yeah, you know, when I came up, I could watch a show like Johnny Carson or Merv Griffin and for weeks at a time, maybe never see a minority perform. And you know, they're out there. So my dream was to one day grow up and show the other side of show business. Unfortunately, you can't get the kind of numbers doing my show, like to be on a network. You know, you can't be on cbs, abc, or replace The King when he leaves on NBC.

[Tonya Moseley]

Johnny Carson.

[Arsenio Hall]

Yes. Yes. So I created this show in syndication, which did very well, and often Paramount thought it was too black because they wanted to kind of dangle a carrot in front of me and say, if you do the right show, you could be the guy to get Johnny's audience when he leaves. But one of the reasons Johnny liked me is I didn't want Johnny's audience, and I didn't want to do his show.

[Tonya Moseley]

When you launched, there were essentially three players. There was Johnny Carson, who was the King, and then Letterman, who was tucked away after midnight. And then you were this scrappy syndicated show with no network. What was Paramount actually asking you to be that you weren't?

[Arsenio Hall]

I guess, you know, the example I like to give people is when Michael Bivens of New Edition first called me and told me he found this group and they're called Boyz II Men. And I said, what are they like? He says, they're like the Temptations, but it's four of them. And I said, hey, I got the Temptations coming on this week. Bring the guys by. If their album's not finished, they can just come on now and do something with the Temptations. So now there are nine black men performing in the center of my stage. And I don't know how to describe it other than there's, you know, one black person in the mix makes it look too black. We've had research that points to that in our society. And I wanted to do a lot of Busta Rhymes, and I had Hammer on a lot. I had everybody in the culture on. And unfortunately, in America, you're never gonna be number one if you have this insatiable desire to do Toni Braxton instead of Dolly Parton. And by the way, I try. By the way, I tried to do both. I tried to mix it up. I would put Dolly Parton on and. And then have something for the culture after it. I wanted to do this show that didn't exist when I was a kid, and I knew the talent was out there. You know, I found Bruno Mars and put him on the show when he was 2ft tall. I wanted those things that Johnny didn't

[Tonya Moseley]

do and the things that you did. I mean, while you weren't number one, I mean, you were a close number two. And in many. You know, in many instances over those years, you overindexed on an audience under 35. And one of the things that you write about in the book is as you were receiving these messages from Paramount that you were Too black that you needed to have different type of guests on. And you were competing against this growing late night ecosystem. It eventually broke through on air. There's a moment on the show when activists from Queer Nation heckle you during your monologue and they yell, why don't you have any gay guests on your show? And at first you answer politely. You say like, I have a lot of gay guests. Maybe they just aren't out. Maybe you just don't know their orientation. But then they continue to push and then you become more agitated and then something in you just snaps. And I want to play a clip from it. Let's listen.

[Audio Clip - Arsenio Hall or Tupac Shakur]

This is my show. This is my show. You understand? This is my show. This is my show, man. You think, you think I haven't had somebody on the show because they're gay? What's wrong with you, man? I'm black. I'm black, man. I'm black, man. I'm the biggest minority you know about. I don't want to hear that gay trash, man. I got gay friends I've had on the show. Because you don't know them or it ain't who you want on the show. You got a problem with it. If you want to book it, get yourself a show now. Sit down, sit down so I can do the show. You've had your say and I've had mine.

[Arsenio Hall]

God, it seems so long ago. I think you become more angry and you become stronger when you realize you are right. Because a huge part of my staff was gay. Many of my guests were gay. But it was at a time when you didn't always know it. So the gay people on my show couldn't even come to my defense. Ellen couldn't come and say, oh, wait a minute, you guys don't know, you know.

[Tonya Moseley]

Cause she hadn't come out yet.

[Arsenio Hall]

Right, right. And Rosie was on the show a lot. And a lot of people that may be still in the closet, so I won't mention their names, but it wasn't my job to say, ladies and gentlemen, balladeer and homosexual, put your hands together for, you know, it wasn't my job to introduce a singer that way. And I think part of my anger was at that point. I. I'm being told by the black community that it ain't black enough. I'm being told by the Paramount executives that it ain't white enough. And now the gay community is going to attack me during the show. You're going to take money out of my wallet and food off my family's plate in the middle of my job here. When you don't know what you're talking about, you're going to blame me for something that is absolutely not true. And I think I was sick of being criticized by everyone because everyone wanted it to be something else. It's hard being the first black anything in late night.

[Tonya Moseley]

My guest is talk show host, actor and author Arsenio Hall. We'll continue our conversation after a short break. I'm Tonya Moseley and this is FRESH AIR Weekend.

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[Tonya Moseley]

You know, you mentioned about holding holding a guest's hand and something that kept coming up in the book were guests who were nervous in ways that surprised me. You tell the story of Maya Angelou coming to your dressing room before the show. She needed like two shots of Crown Royale just to walk out there. And Patti LaBelle. Yeah. The night you introduced Prince, she was gripping in your hand so hard.

[Arsenio Hall]

Yeah. And she has these nails. I still have a mark in my hand from Patti LaBelle.

[Tonya Moseley]

I mean, that stuck out to me because it comes up so often in the book. These are people who had performed for thousands and had been performing for a long time at that point. What was it about your stage or you?

[Arsenio Hall]

First of all? I mean, one of the things that Paramount hated is my audience would be predominantly black and young. I don't know if that had anything to do with it, but it was a different kind of show. Maya Angelou came to my room to talk to me. And she came down and she told me how nervous she was. And I offered her. I said, I got a bar and I opened this cabinet. And she says, oh, baby, I wouldn't mind having a little bit of that. And so we had a drink. And I think it was the time that we talked about hip hop and how it was poetry set to music, but it was poetry of different poets.

[Tonya Moseley]

You know, the thing about the nerves, I mean, maybe that's just something that happens and we just don't see it. But there's something about that that I think maybe there was. There was an environment that you were providing that allowed these guests to show a more truer or fuller version of themselves. And I wanna play another clip from an interview you did with Tupac in 1993. At the time, he was promoting his new album and the film Poetic justice with Janet Jackson. And you asked him about promoting violence. Let's listen.

[Audio Clip - Arsenio Hall or Tupac Shakur]

When we were talking at the top of the show, first of all, you

[Arsenio Hall]

did a little rap, and it contained the word nine.

[Audio Clip - Arsenio Hall or Tupac Shakur]

Now, on the street, that's nine millimeters, right? Oh, you gonna get some lettuce? Yeah, yeah.

[Arsenio Hall]

And I'm wondering, are you concerned that possibly it'll affect box office or record sales because you're too close to the edge or too hard?

[Audio Clip - Arsenio Hall or Tupac Shakur]

It's like this. The masses, the hungry people, they outweigh the rich. So long as I appeal to the hungry and the poverty stricken people, it's all good. I'm gonna have a job for life. It's these rich people who worried about the fooling the poor people. Everybody knows crime out there. Everybody know what type situation we in in the streets. All I'm doing is showing you and telling you, you know what I'm saying? Why get mad at the brother that bring you the news? Get mad at the person that's making it happen. Feel me? It's like, you know, You know, there's a.

[Arsenio Hall]

There's a weird game that goes on because now and now, as a result of your art, you're becoming one of the rich.

[Audio Clip - Arsenio Hall or Tupac Shakur]

Yes, not rich, but they giving me checks more often.

[Tonya Moseley]

That's Tupac Shakur on the Arsenio hall show in 1993. And you know, this is kind of a serious moment. You're asking him a real question, Arsenio. But throughout the interview, here's Tupac is smiling. The two of you are giggling. Through so much of it and watching it, I kept coming back to something that I can only describe as black boy joy. It's something that we've been talking about lately, like over the last few years. And so then I started watching all of the YouTube videos. Will Smith, Prince, Sammy Davis Jr. Muhammad Ali, Michael Jackson, Eddie Murphy. It goes on and on. There was a giddiness, this looseness aside of these men that we didn't see anywhere else. And what do you think it was about your stage that made black men in particular feel free?

[Arsenio Hall]

While there might be a different answer to that question for each artist, like Tupac and I, we had a lot of history. The first time I met Tupac, he was with Jada Pinkett. It was way, way back, and he was a dancer. The next time he came, he came as a rapper. The next time he came, he came as an actor. I remember him calling me and wanting to come and just talk once, because he said that he was about to do poetic justice and they wanted him to take an AIDS test. And he said, arsenio, am I wrong? I shouldn't have to take an AIDS test unless I'm going to really have sex with Janet being Janet Jackson. And it was funny because now when I look back now you may go on Instagram live or you may tweet something. Back then, we didn't have the Internet. We didn't have the Bluebird. We had the Blackbird. That was me. I was the place you come and talk and air out your grievances and say what's on your mind. And I think people knew it was that place. So you get that boy joy. You get that other side that you've never seen. Maybe it's those guys knew we were kindred spirits. I remember Ice T coming on when he had an album out called Cop Killer. And I really wanted him to explain it, because when I use those two words together, it sounds horrible. And the 9 millimeter conversation with Tupac. But these were poets from the inner city trying to give you a poem a little different than E.E. cummings. And I remember Ice T saying, you watch a Schwarzenegger movie, but you don't think he's really the Terminator. You don't think he's really killing people. Right? I am like that. This is art. I'm telling you about a problem that my people have in the inner city with cops. And that's one thing I loved about the show is the masses. White America, let's say, in the safety of their home, could look in this box and hear people talk and hear thoughts that they didn't hear in their homes. And that's why I thought the show was important.

[Tonya Moseley]

I want to talk a bit about just how purpose driven you were as a young person. From a very young age, even in the single digits. You hosted your first talk show in your apartment building basement when you were 12, and your musical guest was a kid from down the street singing along to a Temptations record. Yeah, Junior Brown.

[Arsenio Hall]

Yeah.

[Tonya Moseley]

And seven kids showed up as your audience.

[Arsenio Hall]

Absolutely. And I used a folding card table as my desk. And, you know, I had a little record player. So I was like, junior's gonna sing Get Ready and I'll put the needle on the record. And it started playing, dun dun dun dun dun dun dun dun. And Junior sang Get Ready. And then I interviewed him. And I had seen a comedian open for Al Green when I was a kid, and. And all he had was a towel on a stool and a glass of water. And I was like, God, I think I could be a stand up. Because sometimes when I would talk during my magic act, I could get laughs. And one time, my dad was preaching a wedding. My dad was a Baptist preacher, and I said something during the wedding and got a laugh from the audience. But my dad was mad at me because we were there. He brought his son to do a wedding, and I'm trying to get laughs. The bride and the groom kissed, and it lasted a little longer than normal. And I, at 5 years old, screamed out, kiss her. Don't kill her. And I got a laugh. And it was like a drug that I chased the rest of my life. And I'm still chasing. I love the laugh.

[Tonya Moseley]

Your father, as you mentioned, was a preacher, and he thought that show business was the devil's business. But you write about watching him preach. I mean, and if we know preachers, they're prowling the pulpit, they're whispering and shouting and women jumping up and down and dancing in the aisles. That's like a real sanctified type church. And you. So in many ways, we're watching a performer. And your dad, do you think he ever saw himself that way?

[Arsenio Hall]

He had to know. And he was part of my dream. My dad, when I was four years old, he took me holding my hand into the pulpit, because you could get to the church pulpit from his office, or as they called it, the pastor's study. And he sat me behind him. So my POV was this church and this crowd. And I watched how he moved them with just his voice, with just the gospel and his ability to entertain and preach. It was scary because now when I look back, that was the most important Sunday of my life. When he let me do that, eventually in coming to America, I got to be a preacher. Cause he always wanted me to be a preacher. He wanted that to be the family business. And I think he would have enjoyed Reverend Brown in coming to America.

[Tonya Moseley]

You're right. That's all I wanted then and now. I wanted my dad to be proud of me. Do you think that the Arsenio show was in some way for him?

[Arsenio Hall]

You know, I've never thought about that angle. I've never had anybody ask me that. But maybe you're right. My father was not a part of the secular world. He, like I said, he didn't even want me to go to Hollywood because he thought that just Hollywood was a horrible place. And I get where he was coming from, which is probably why I've tried to live my life in a way that would make him proud. And I've fallen off the wagon and tripped from time to time, but. But for the most part, I think he would be proud of me. And I think every parent just wants their child to be happy. And happy is often success. It's hard to be happy and content in this world we live in.

[Tonya Moseley]

Thank you, Arsenio. It's been a pleasure.

[Arsenio Hall]

Thank you.

[Tonya Moseley]

Talk show host and author Arsenio Hall. His new memoir is called Arsenio. Terry has our next interview. Here she is.

[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 mitzvahs 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 affairs. 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, he was 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 Ross produced and co hosted. Here's Jeff Ross.

[Jeff Ross]

Snoop, love you, man, so much. The only person that's inhaled more smoke 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. Herschel.

[Terry Gross]

Jeff Ross, it's great to have you back on the show and that stuff is so funny.

[Jeff Ross]

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.

[Terry Gross]

Well, it's great to have you. So to the extent that you're comfortable talking about it, how is your health now?

[Jeff Ross]

My health is 100%, thank you for asking.

[Terry Gross]

Oh, that's such great news.

[Jeff Ross]

I just had my chemo port removed.

[Terry Gross]

Oh, great. Cause you still had it on when you were filming the show, the Broadway show.

[Jeff Ross]

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.

[Terry Gross]

I want to talk now about how you became you.

[Jeff Ross]

Yeah.

[Terry Gross]

So let's start with the catering business. My parents were such veterans of catered affairs, weddings and bar mitzvahs at various catering halls around, like, Queens and Brooklyn. And 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?

[Jeff Ross]

Newark was on Clinton Avenue, was Clinton Manor, and eventually moved to Route 22 in Union, New Jersey, where I worked there as a boy and a young man.

[Terry Gross]

I want you to describe what the typical bar mitzvah was like when you were working in the kitchen.

[Jeff Ross]

You know, I would ride my moped on the turning lane of this highway 12 months a year to go to my family owned catering hall where these lavish affairs would happen. So I saw human nature, people at their most nervous. Brides, grooms, mother of the bride, father of the groom. You saw people at their most intense. I would watch the bands from a window in the kitchen. You know, I would like peek 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.

[Terry Gross]

Oh, maraschino cherries.

[Jeff Ross]

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 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 canister and I would roll meatballs for hours. Or in my teens I would feed the workers. I would make matzo braai for 80 people on a Sunday morning. The servers were all Scottish and Irish. There were Haitian people, 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.

[Terry Gross]

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 parents lives. So when they'd go to like a catered wedding or bar mitzvah, they would just eat and eat. And there's so many stages of food. Like at the catered affairs they'd go to, there'd be a smorgasbord which would have like sculptures of chopped liver and like charmaine was the Chinese dish. There were Swedish meatballs and duchess 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, category 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 then everybody would have like a very sore stomach afterwards.

[Jeff Ross]

But everyone felt like a king when they left. You know, the Viennese table was dessert. Wasn't the Viennese table dessert? Halava and ice cream and cake and

[Terry Gross]

oh, maybe, maybe it was just jello molds. But then after that, I remember once there was a breakfast. I mean, and I thought, this is insane.

[Jeff Ross]

You know, I think we might be finding a direct connection from the kosher catering business to me getting colon cancer. I think we just figured it out.

[Tonya Moseley]

We're listening to Terry's conversation with comic and roastmaster Jeff Ross. He has a new Netflix comedy special called Take a Banana for the Ride, a film of his autobiographical one man Broadway show. We'll hear more after a break. This is FRESH AIR weekend.

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This message comes from BetterHelp. As a dad, BetterHelp President Fernando Madera relates to needing flexibility when it comes to scheduling therapy.

[Arsenio Hall]

I have kids under 18, so, like, time is very limited.

[Jeff Ross]

That's why at BetterHelp, our therapists try to have sessions, sometimes at night, depending on the therapist or during the week. So I think that's what we need to tell the parents. You're not alone. We can help you out.

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[Terry Gross]

Were you brought up religiously or culturally Jewish?

[Jeff Ross]

Culturally, bar mitzvahs, all that stuff. I did it, but it was a struggle.

[Terry Gross]

What was your bar mitzvah like? Was it lavish?

[Jeff Ross]

My bar mitzvah was like something between a Super bowl halftime show and, like something, you know, Saddam Hussein would throw for one of his kids. Like every favor of New Jersey Was called in, you know, the 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 babka. It was, you know, it was a beautiful bar mitzvah. I remember the first three words of my Haftorah. 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.

[Terry Gross]

When you were 12, your mother was diagnosed with leukemia. She died when you were 15. Were you very close?

[Jeff Ross]

We were. We were.

[Terry Gross]

What was it like watching her suffer when you were so young and you probably hadn't seen someone suffer like that before?

[Jeff Ross]

It was. It was hard. It was hard. It was hard to see somebody so tough and 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.

[Terry Gross]

What caregiving responsibilities fell to you? Your father was really busy with the catering business,

[Jeff Ross]

besides the having to take care of yourself for her, you know, she wanted to make sure while she was in the hospital that I was. My sister and I, you know, I was playing football. I was washing my uniform every night and making my own dinner and just being a good. 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 mom a 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'll be 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. My dad would take us to Broadway shows to cheer us up after the hospital visits. And the king and I, Yul Brenner, you know, so I made a joke about that, you know, that she would look like Yul 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 was 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 for redemption from my 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 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. To laugh along with it? But I do think the greater mission is to inspire people and give people hope about their. Whatever's going on in their life.

[Terry Gross]

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.

[Jeff Ross]

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. 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. 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 have this new baby that was born over there. And now here it is in 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.

[Terry Gross]

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 till he died. What was it like for you to be taking care of him? I know you liked him very much. You were close.

[Jeff Ross]

Well, that was my. I felt experienced. I understood 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. I loved him. 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. My 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, 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 drive into 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.

[Terry Gross]

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, you know, talk with people and cry and laugh about the person who you're grieving. Did you do that?

[Jeff Ross]

Yes. My mom died slowly. 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. 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 parties with him. And, you know, Ronnie, Ronnie Lifschultz, 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 this be? His estate was a complete mess. He had a 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 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 me's. 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.

[Terry Gross]

Right. I'm seeing you in such a different light. You know, I'm so glad that you did the show and are showing us this side of yourself. It's, like, so 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 and remake yourself into the person who you wanted to be or thought that you were.

[Jeff Ross]

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.

[Terry Gross]

Were you the guitarist or whatever?

[Jeff Ross]

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.

[Terry Gross]

How'd you figure that out?

[Jeff Ross]

I didn't. Someone did it for me. My friend Mark, who I name check in the, in the Netflix show. He was taking a stand up 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 5 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. I understood that I loved comedians, like as a kid 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 cause 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.

[Terry Gross]

You knew some of those old school comics. You knew Buddy Hackett. And you knew Don Rickles. You joined the Friars Club when you were how old?

[Jeff Ross]

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 Berle or Buddy Hackett sitting under their own portrait.

[Terry Gross]

So we have to wrap up soon, I regret to say, but I have a request.

[Jeff Ross]

Anything.

[Terry Gross]

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.

[Jeff Ross]

Oh, wow.

[Terry Gross]

On a scale from really grateful for the hilarity to I will be gorgeous for the rest of my life. And if I really hate it, I can insist that we edit it out.

[Jeff Ross]

Terry Gross. Terry Gross has been around so long, she interviewed Ed Sullivan.

[Terry Gross]

I wish I did.

[Jeff Ross]

Terry Gross, a barely living legend.

[Terry Gross]

That's great. Well, it's been a pleasure to talk with you again.

[Jeff Ross]

Really. Always, always enjoy this. You always find something in me that I didn't know was there.

[Tonya Moseley]

Jeff Ross speaking with Terry Gross. His new comedy special, take a Banana for the Ride is now streaming on Netflix. Fresh Air Weekend is produced by Teresa Madden. 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 Myers, Roberta Shorrock, Ann Annemarie Baldonado, Lauren Krenzle, Monique Nazareth, Thea Chaloner, Susan Yakundi, Anna Bauman and Nico Gonzalez Whistler. Our digital media producer is Molly CB Nessber with Terry Gross. I'm Tanya Moseley.

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