The Comedian Who Found Success Insulting Celebrities Made a Surprisingly Emotional One-Man Show — But More Roasts Are Coming, Too

If you’re not familiar with Jeff Ross, he is best known as the “Roastmaster General” — a three-decade master of the savage comic sport introduced by the Friars Club in the 1950s, in which a procession of comedians and wannabe smart-asses barrage a roastee with decidedly no-holds-barred insults crafted to evoke laughter and gasps. Ross is also executive producer of Netflix’s celebrity roasts as well as a writer and a performer on them, including the headlines-making mocking of former NFL quarterback and seven-time Super Bowl winner Tom Brady.

Ross was the subject of many of the headlines that the Brady roast generated because he directed a “massage” joke at Patriots owner Robert Kraft, who was arrested in 2019 for soliciting prostitution in a Florida massage parlor. (The charges were dropped.) The joke prompted Brady — who took most of the barbs directed at him with grace — to walk across the stage and whisper to Ross, whose microphone was live, “Don’t say that s—t again.”

Brady and Ross embraced after the comedian’s set, but Kevin Hart, who hosted the roast, had an insult waiting. “Make sure to check out Jeff’s one-man show. It’s playing at the Hollywood Cemetery,” Hart said. “His career is literally dying. If we stop doing these roasts, you will not see Jeff Ross ever again.”

Hart was dead wrong. Ross does have a one-man show, Take A Banana For The Ride, which opens on Broadway at the Nederlander Theatre on Aug. 18 and runs through Sept. 28, and its humor is nothing like the brand of comedy for which he is best known.

Take A Banana is a sweet, heartfelt — and very funny — autobiographical homage to his parents, his grandfather (the show’s title comes from him), the German Shepherd rescues that brightened his world at a low point in his life, and three good friends who died too soon: the comedians Gilbert Gottfried, Bob Saget and Norm Macdonald. It also delves into Ross’ battle with colon cancer, and the circumstances and inflences that led him to become a comedian. There’s music, too, which Ross wrote with another comedian, Avery Pearson. One song is called, “Don’t F—k With The Jews.”

In his dressing room at the Nederlander following a rehearsal, Ross spoke to Billboard about the origins of his one-man show, his career in comedy, the foreclosure and sale of the New York Friars Club’s landmarked townhouse headquarters and that Brady roast. “You know I’m in it, man. I’m f—king in it,” he says. “This is one of the craziest, most surreal moments of my life.” And he’s loving it.

Take A Banana For The Ride is the last thing I expected from you.

You need to make that your headline. It sounds like a compliment.

How does a guy known as the Roastmaster General create such a touching, heartfelt show?

I started writing it long before I was the roast guy. The heart of it happened before I discovered the roasts — or the roasts discovered me. I started writing stuff down and saving stuff in high school. There are actually things from high school that I found in notebooks that are in the show.

And in the mid-’90s, I started doing this show because I wasn’t really hitting it as a standup yet. It even had the same title. I did it 20-30 times. I certainly hadn’t found the roasts yet. If anything, the roasts are what took me away from the show.

This was obviously before the cancer diagnosis and your dogs. You’ve added a lot.

I forgot about it for 20-something years. I didn’t forget about it, it just wasn’t interesting to me to look back. It wasn’t the cancer diagnosis that inspired the look back. It was losing Gilbert [Gottfried] and [Bob] Saget and Norm [Macdonald]. That made me look back and go, what was I saying about grief and mourning and bouncing back and resilience when I was a kid, compared to how I feel now? That inspired me to revive the old show.

The show is also about the life experiences that led you to become a comedian.

It was the trickle of living in New Jersey where ball-busting is the love language — where all the radio stations and sports teams say they’re from New York, so you get a bit of a chip on your shoulder. It was working in my dad’s catering hall as a boy and as a teenager. My entire childhood was being the boss’s son and having all the Scottish and Irish waitresses and waiters, the Russian guy making fruit salads, the Hungarian guy who made the Jell-O molds and the Haitian guys in the kitchen busting my chops for being the boss’s son. Getting bullied as a little kid and my mom dragging me off to karate school. It’s all of these things. They toughened me up. The origin story, at least how I tell it in the show, is all this stuff. If I had to point to one pivotal thing, then it’s that first roast.

That’s right, you got your black belt in karate when you were quite young.

Second youngest black belt in the United States. Good luck researching that one.

Does it help with being a comedian?

It helped get me the confidence to talk smack for a living, for sure.

How did you bring this show to Broadway?

That was something I was saying as a joke. Oh, I’d love to do it on Broadway. Or other people would say it, and I would do superstitious stuff like my mom did. She used to go ptuh-ptuh-ptuh. Then, in the last couple of years, Jim Carrey taught me about manifesting. He said, “If you don’t believe it, who’s going to believe it? You have to speak it into truth.” That also motivated me to make the show better. To make something really great is an unbelievable amount of work — whether it was getting my black belt at ten-and-a-half or producing The Roast. Then, by chance, an old Friars Club pal, Marc Cornstein, grabbed ahold of the idea of taking it to Broadway. He started raising money and hooked me up with the Nederlanders.

There’s a musical element to Take A Banana For The Ride. You have a keyboardist and a violin player onstage with you.

Asher Denberg is our musical director and the keyboardist onstage. Felix Herbst is the violinist. Having some music in the show is my way of paying tribute to some of the older comics who always did that type of thing. There’s a song about my dog from the voice of my German Shepherd, “You’re One of the Good Ones.” And there’s the singalong about my family and my origin story called “Don’t F—k With The Jews.”

I love comedians, but I also really love musicians. I love Broadway music. We’re listening to show tunes all day in my dressing room and at rehearsal. So being able to work in a world-class theater with world-class musicians — comedians always say they want to host the Oscars. For me it was always the Grammys. I love music, and I love the musicians and a bunch of them are coming to opening night.

You wrote the songs?

I co-wrote them with my friend Avery Pearson.

What are some of the show tunes you listen to backstage, and do you like any contemporary artists?

I love new music. Chappell Roan and Olivia Rodrigo are favorites — and I first saw Benson Boone at Clive Davis’ Grammys party, and instantly fell in love with his music and showmanship. But in the dressing room before my show, I’ve been listening to Man of La Mancha a lot. I’ve been very influenced by “The Impossible Dream” and “Man of La Mancha.“ Maybe because my parents had the 8-track.

How did you get into the roast business?

It was a happy accident. I have to credit my pal Greg Fitzsimmons for inviting me to his dad’s honorary golf tournament. It was a Friars Club tournament at a golf club in New Jersey, and [Friars Dean] Freddie Roman was teasing me and picking on me because no one knew who I was. I walked up and started making fun of him. He was so loud and boisterous. I said they call him Freddie Roman because you can hear him in Italy. It was such a small joke, but no one had ever taken a swing at the head of the Friars before, especially some goofball kid that nobody knew.

Months later, they couldn’t get any stars to do the roast. It was corny and antiquated. I got the call from [executive director] Jean-Pierre [Trebot] at the Friars Club. He said, “You were funny at the golf club. Do you want to do the roast?” I had to go to the Museum of Broadcasting to see what the roasts were about. This was 30 years ago, so I couldn’t look it up on Google or YouTube.

I was more into the rock ’n’ roll comedy of Steve Martin, Eddie Murphy and the Blues Brothers, but I said, “This is kind of funny.” I’m kind of like this anyway. I didn’t really care much about Steven Seagal, who was being roasted, but I was taken by the idea of being up there with Buddy Hackett and Henny Youngman and Milton Berle who were all there at my first roast.

You made it into a career.

Well, it became my lane. There were years where it was lucrative but not necessarily cool. And then I got advice from Dave Chappelle that it was my job to make my lane a six-lane highway. I embraced that and realized I can’t keep waiting for celebrities to agree to get roasted in a tuxedo. I have to figure out other ways to do it. That birthed the idea of me speed-roasting volunteers from the audience at my standup shows, the roast battles and the historical roasts. I even roasted at a jail. It’s on Paramount+. Jeff Ross Roasts Criminals Live from Brazos County Jail.

Is it true that celebrities would hire you to write jokes so that they would look good when it was their turn to roast or to be roasted?

I wouldn’t say I was hired by them. I was always a producer and a writer on those shows, and part of my responsibility would be the booking, writing, the promotion and appearing on the show. Back then, The Roast had a small budget, and we did everything. I wore a lot of hats — I guess I still do, but I have a lot more help now.

Roast jokes are often politically incorrect, anti-woke — whatever terminology you prefer. What do you make of the whole woke vs. anti-woke humor debate?

I feel like it’s something that everyone talks about except the comedians. To me it’s binary in a different way than woke or not woke. It’s funny or not funny. It never affected me. People are telling me that the Tom Brady roast – because there hadn’t been one in five years — helped recalibrate mainstream comedy a little bit back to let’s call it normal or edgy or irreverent. I’m proud of that notion, but in Jeff Ross Land it’s always roast time. It’s just that the rest of the world is catching up.

I saw it firsthand Saturday night after the show here at the Nederlander. I went out to sign Playbills and say hi to people, and there were three sets of teenage boys with their dads. I found it striking that 13, 14, 15-year-old boys were knowing me from the Tom Brady roast. From there they look at the Justin Bieber roast and the jail roast. Then they go “Oh, that’s roasting. I’m going to do that with my friends.”

It’s a sign of affection. It’s their version of karaoke. That makes me immensely happy.

That was always the motto at the Friars Roasts. We do it with love.

I always felt like the roasts were the extensions and celebrations of friendships. I feel like my show is similar. It’s a tribute to some of the people who made me who I am. Because it’s about them I can do it every night. If it was only about me, I would have a hard time getting past the first week. I would get bored. But I really feel proud when I’m standing there and the video message that Bob [Saget] sent me plays or Gilbert sings a song from Fiddler on the Roof. They’re getting one more turn at the mic.

Do you have any rules for roasting?

My general rule for roasting is to only roast volunteers. Once they opt in, anything goes.

What went through your head when Tom Brady said what he said to you at his roast?

Virtually nothing was going through my head when Brady interrupted me, except “keep going.” We were having fun, and I always love a little verbal sparring during the roasts.  Tom was sticking up for a father figure, and I respect that. Mr. Kraft was very gracious, and a great sport afterwards.

Was Brady aware of how vicious his roast was going to get?

I don’t think any of us knew how rough that roast was going to be. I mean, from the get-go: Kevin Hart, me, Nikki [Glaser], Tony [Hinchcliffe] Andrew [Schulz], Gronk. We all went as hard as we could. And once you see Tom being a good sport and taking the jokes so well, you put your foot on the gas.

But the real bravery was Tom saying yes in the first place. You’ve got to give him credit for agreeing to do a roast after no one, for five years, would say yes. This guy had the thick skin and was so confident in who he was that he said, “Yeah.”

I said to him, “Why are you doing this?” He was like, “I love the roasts, and I want to bring it all back.” To his credit and I guess to the credit of the roast, everything he would want from his life career-wise seems to have worked out great. He immediately became part owner of a team. He immediately launched this incredible broadcasting career, and he’s doing Super Bowl commercials with his old teammates. I feel like the roast kind of melted away some of the ice that he may have had with his coach and his owner and maybe even his players. I think it did a lot for him.

Are there more Netflix roasts on the boards?

We have something cooking, but I can’t talk about it yet.

What do you make of the Friars Club’s New York headquarters being sold in foreclosure?

The Friars Club thing hurts because it feels like that’s my alma mater. It especially hurts now because I always had this fantasy of doing a Broadway show, then going to lunch at the Friars Club and having everybody come over and tell me how much they loved it. This would have been a great time to be a Friar for me.

Now I’m at the Yard House. It’s not quite the same. The jambalaya is good, but it’s not quite the Friars Club, where you would see people in the steam room, in the gym and there was a poker tournament, a pool tournament, a charity fundraiser. And then there were big events like the roasts. That is sadly in the past, and it breaks my heart.

In terms of manifesting what’s next for Jeff Ross?

A cup of tea. A puff of weed. Get into my costume. I get to ride this incredible wave of emotions and laughs every night for the next two months. I’ve never done anything for two months in comedy. I’m not looking past this. When I was a young — before I became a comedian — my Aunt Bess would take me to Broadway shows. She took me to see Jackie Mason do his one-person show. I thought it was so cool. He didn’t have dancers, he didn’t have music, it was just him ripping the roof off the theater for an hour-and-a-half. I was like wow, that is the pinnacle of show business. If I can do that then I’m good. I can see myself retiring. That’s how much I like doing this gig.