Insult king Jeff Ross probably will cry during his five-night run in Minneapolis

Those who dream of being tortured by Jeff Ross will get their chance when the mastermind behind “The Roast of Tom Brady” takes over the Parkway Theater for five straight nights.

But before getting ridiculed, fans will get something they might not expect from the reigning insult king: a therapy session.

“Take a Banana for the Ride” is a departure from Ross‘ usual zinger-oriented act. It revolves around his New Jersey childhood, during which he lost both his parents. The journey may get even more emotional on the latest leg of his tour. Since he last performed the one-man show, Ross was diagnosed with cancer. He says treatment has been successful, but declined to elaborate.

The comic displayed his sincere and soft side last month during a Zoom interview, which was slightly delayed so he could phone his sister and wish her a happy birthday.

Q: You first experimented with this idea 30 years ago. Why did you resurrect it?

A: I lost three buddies during the pandemic. Bob Saget, Gilbert Gottfried and Norm Macdonald. I started looking back at the losses I had as a young man and realized I had a lot of experience in resilience. I was too mentally fragile to sustain the show back then, but now I’ve got 30 years of wisdom to lay over the top of it. And better jokes.

Q: How much do you incorporate your cancer diagnosis into the act?

A: We’ll find out in Minneapolis. I did the show last year, but I didn’t get sick until recently. I’m still trying to figure it out. I don’t want the show to be maudlin, but I think it’s important to address it. Norm was very private and hid his sickness. I didn’t think that was fair to the audience and his friends, so I’m putting it out there. But I don’t want people to feel sorry for me. It’s going to be a very empowering and bold statement on how to get through tough times.

Q: Do you worry about alienating audience members who come expecting 90 minutes of insults?

A: I went into this a little paranoid, because I don’t want people thinking they’re coming for one thing and then getting something else. There is a lot of roast talk. At the end of the show, I ask for volunteers who want to get roasted. But I haven’t experienced any buyer’s remorse. If anything people say, “Oh, that was such a fun surprise. I never saw you like that before.” That’s been very gratifying to me.

Q: How many times have you cried during the current show?

A: Almost every time, always at a different point. I can’t express how emotional the show is. What I’ve learned to do is build up the pressure, pressure, drama, pressure, then — boom! — you release it with a big joke.

Q: Whenever I saw Don Rickles live, he always did a tribute to his mom. Are insult comics really softies?

A: I think you have to be able to get away with it. There are comics who are mean just to be mean, and that can be very entertaining. But I’ve gotten away with it for so long because I only roast the ones I love. If I ignore you, that’s the ultimate insult.

Q: Because you lost your parents at such a young age, were there comics that served as a father figure?

A: Buddy Hackett was the closest thing I had to a mentor. Like a lot of old celebrities, he had his weird moments, but he was very generous with his wisdom. Comedy was like No. 10 on the list of things Buddy was an expert on. And he made a great matzo brei for breakfast.

Q: When you roasted Rob Lowe on Comedy Central in 2016, you dressed up as Prince, who had died a few months earlier. Did you get any blowback from that decision?

A: Prince didn’t have a lot to do with Rob Lowe, but he had a lot to do with me and my life. I loved Prince. My phone is purple. It felt like the right way to pay homage and make a splash in what wasn’t the most exciting roast. Another reason I’ve been able to do this for so long is that I surprise people as opposed to hitting the same notes all the time.

Q: Who is on your dream list of people to roast?

A: I think a Drake roast would be fun. Tiger Woods would be a great roast.

Q: Do you think Tiger would ever do it?

A: I think at a certain point, people have nothing to lose. Everybody wants to be the center of attention, even when there’s a target on their back.

Q: If you’re trying to get Tiger, it might help to recruit some pretty blondes.

A: Pretty blondes help every show.

When: 7:30 p.m. Wed.-Sun.

Where: Parkway Theater, 4814 Chicago Av. S., Mpls.

Tickets: $55-$75, theparkwaytheater.com.