Jeff Ross, who plays David A. Straz Center in Tampa, Florida on Oct. 26, 2024. Credit: Photo c/o Straz Center

Jeff Ross’ grandpa didn’t have a lot to say to him when the then-fledgling comic would come home to Jersey after a grueling day of cutting his teeth on the New York City comedy circuit.

“Back then, it was survival mode. He was kind of in and out of lucidity,” Ross, 59, told Creative Loafing Tampa Bay.

That was a time before streamers shelled out big bucks for comedy, or audiences put cell phones in Yondr pouches. If you did stand up in the early-’90s, people assumed you were also a drug addict, lost your job, or failed out of school.

“It didn’t make any sense. I didn’t grow up around show business. So to say I was out doing comedy was, like, ‘Yeah, I’m a stripper now, pop,’” he added.

Ross’ mom died from leukemia when he was just 14 years old; his dad passed from cocaine, as he’s described it, five years later. After that, Grandpa Jack raised him. Ross didn’t realize it but the roles had reversed by the time he got into comedy.

“I was taking care of him. It was just sort of how we survived. He would give me a few bucks and some encouragement and some advice, and I would take him to his doctor appointments and check on him when I came home,” he added. “It was just sort of day-by-day kind of existence, wondering how long he would last—and wondering how long I would last as a comedian. It was all sort of treading water.”

And while grandpa didn’t have a lot to say, he did regularly offer something before he walked out the door.

“He’d say, ‘Take a banana for the ride,’” Ross has explained in interviews. He would regularly decline, but then think about the fruit when he was stuck in the Holland Tunnel seven hours later and hungry as hell.

It took Ross some time to figure it out, but the banana was a way for Grandpa Jack, a WWII veteran, to tell him that he wished he was coming, too.

That banana, and a whole lot of emotion, is baked into a new show Ross—who recently roasted the hell out of former Tampa man Tom Brady—brings to the Straz Center on Saturday.

“Take A Banana For The Ride” includes two Berklee-trained musicians, pianist Asher Denburg and violinist Felix Herbst. Ross’ longtime collaborator, Stephen Kessler directs.

“It’s got music, it’s got laughter, tears, but mostly laughter,” Ross—who loves Tampa’s museums, history and party scene—added. “It’s a human experience that plays out on stage.”

There’s a roast of volunteers at the end of the show, but it’s a different approach for Ross, who first tried to do a version of this show three decades ago, only to find that he wasn’t emotionally ready to do it.

Ross, who now has 30 years of wisdom to bring to the set, said he’s still nervous about doing it, despite being a little more emotionally secure. The death of three friend—Bob Saget, Norm MacDonald, and Gilbert Gottfried—forced him to revisit “Banana” and the feelings he had about the loss of his grandfather and parents. Ross found that he is still feeling a lot of the same things, but still resilient, too. He’s worked hard to bring all the concepts together for a show that is from the heart, but funny, too. He calls the experience a rollercoaster of emotions.

“Everybody starts to see their own problems, their own family in my stories, and in the end, I think everybody leaves with a smile on their face,” Ross added.

There’s really only been one person who didn’t break out in laughter around Ross: Former president Trump, who’s been roasted twice, but remained stone faced through much of the specials.

“I told him, ‘If you laugh a little, you’ll give us something to cut to, rather than cutting to the audience laughing at you, they’ll be laughing with you,,” Ross explained, adding that Trump got it and loosed up a bit. “But I think that’s his shtick to seem unfazed, and I guess it’s worked for him, because it’s he managed to roast battle his way into the White House at one point.”

Ross would not tell CL who he’s casting a vote for in the election, but anyone who’s seen “Jeff Ross Roasts The Border” can probably guess.

In that 2017 special, Ross goes to the flashpoint of America’s obsession with immigration and talks to families fleeing violence, and some who spend their lives trying to help those whose own existences have been shattered. It was Ross’ attempt to go see what was happening for himself instead of letting others explain it to him. He said he thinks about the experience all the time since immigrants are such a huge part of the American experience.

“No matter how you feel about the politics of it, you can’t argue with the fact that these are nice people with big families looking for opportunity,” Ross said. Immigrants come to the border, but they run it as patrol agents, too, he added.

“They’re all Mexican Americans. We’re all one big hodgepodge, one big family. And I didn’t want to lose sight of that. I didn’t want people to forget that, and I wanted to give them a big hug,” he said.

A hug is what he hopes Tampa Bay gets with “Take A Banana For The Ride,” especially after the double-whammy of Helene and Milton. At this point in his career, the jokes come easy for Ross, but he’s looking to find the bigger message now.

“I want people to talk about it for days and weeks and maybe even have it affect the way they think about their own lives and their own mortality,” he said. “For me, the bigger message is: How do we bounce back from tough times?”

We’ve been finding out over the last few weeks in Tampa Bay. And on Saturday night, it’ll be nice to have a laugh about it.

Tickets to see Jeff Ross play Ferguson Hall at David A. Straz Center for the Performing Arts in Tampa on Saturday, Oct. 26 are still available and start at $46.

Subscribe to Creative Loafing newsletters.

This article appears in Oct 24-30, 2024.