By Dan Snierson
June 11, 2015 at 12:00 PM EDT
Bob Levey

He has done gigs in plenty of bars, but now he’s doing one behind them: Roastmaster General Jeff Ross gives a hard time to the inmates doing hard time at a Texas jail—and learns a lot about them in the process—in his intriguing Comedy Central stand-up special Jeff Ross Roasts Criminals: Live at Brazos County Jail (June 13, 11 p.m.). EW used its one phone call to dial up Ross and ask him how he braced for the most dangerous and outrageous gig of his career.

EW: Obvious first question: Why?

JEFF ROSS: I roasted Bieber. I roasted Sheen. I thought,  “What’s the next level of criminal I could go after? An actual criminal!” Why? I wanted to do something purposeful. So much of comedy is just getting drunk, getting stoned, entertaining people on a date or at a bachelor party, and I wanted to do something that means something, where I actually learn as I’m doing it. I’ve always been fascinated by criminals. Who are they? Why do they keep coming back to jail in large numbers? Do they have a sense of humor?… I wanted to do something that would enlighten people, not make it about the politics but about the people.

Early on, somebody who had been in prison, somebody really smart, explained to me not to call them prisoners or inmates but to call them people. As soon I understood that, I felt like I knew how to engage them and roast them. I could have been just as messed up as a kid. And I’m lucky. I got just enough education, just enough parental guidance, and made some better decisions. But I sold weed in high school. I did a lot of dumb stuff. I don’t know if I would have survived the system… Although I was on tour with Charlie Sheen once. I survived that, I could probably survive jail.

Were you surprised that any prison would let you do this?

When I first pitched it to Comedy Central they said, “Other comedians have tried this before. There is so much red tape. You’ll never it get done.” All last summer, all last fall, I wrote letters. We visited jails. My producers [Stuart Miller, Denni Graap, and Asaf Kastner] went down to Tent City in Arizona. They gave us permission then reneged…. There must’ve been 150 rejections. All these jails and prisons kept saying no, yet I kept writing a standup act just for this show. And you’re going into Thanksgiving, Christmas, and New Years, and then Valentine’s Day. I’m doing jokes about solitary and minimum sentencing and the death penalty in front of Valentine’s Day audiences—I was the ultimate buzz kill comedian for eight or nine months. We got a little discouraged, but I kept thinking,
“I only need one to say yes.”

Out of desperation, we took an ad out in a jailer’s trade magazine—the Variety for law enforcement. We got a call back from [jail administrator] Wayne Dicky. He got it and his team got it. His main requirement was that we would pay for extra security, because to get 200 people into one room is a challenging exercise for the guards. And he wanted a month’s notice so that he could use that as an incentive for good behavior. Even those Nazis had to behave for a month to get into my show.

Were there ground rules set up for your act?

There really weren’t any. What they did point out to me was there are laws—it might even fall under American workplace laws—where you’re not allowed to make certain types of jokes about prison rape. I thought that was interesting. That’s a good comedy filter too. The “drop the soap” jokes have all been done, you know? Even for a second there, I thought a funny title for the show would be “Don’t Drop the Mic.” But in a weird way they did me a favor because I don’t make those jokes in the show. It keeps the comedy sort of—not highbrow, because that’s not my thing, but it keeps it out of the gutter. And I like that. I don’t take the easy joke.

Whom did you ask for advice? Did you talk to your comedian friends? Monique did that special in a women’s jail…

I watched Monique’s [2007] special. She did something cool, more of a motivational talk. There’s a couple comedians that you wouldn’t know have done time and I asked them for advice. I talked to a bunch of ex-cons. I talked to different prisoner advocacy groups about what might be funny, what might not be funny. But my research was more academic. I wanted to learn more about incarceration. We say we’re a free country but we have more people locked up than any other place on Earth. Somebody told me that one out of every 100 Americans is locked up. It is like the largest growing demographic I could perform for. There are so many people going to jail, I want them on my side. I’m really big with men 18-49 doing 18 to 49…

What kind of research did you do on the inmates? In the special, you hang out with the prisoners, hear their stories and visit solitary confinement.

I was there three full days… I didn’t want to make a joke out of it. I wanted to take it seriously and that’s why I went down early. I always try to roast things from the inside out and be almost like a chameleon. I wanted to live in that environment. I didn’t want to be an inmate. I didn’t want to be a guard. I wanted to be a comedian dropped into this environment and see how they react to me. And because I’m not a journalist, I feel like they opened up to me in a new way.

Even though you spent some time getting to know the inmates, how scared were you while doing the roasting, on a scale of 1-10?

Ten. I was terrified. First of all, there were no guns [carried by the guards]. If somebody comes on stage as a volunteer to be roasted and they don’t like what I say or they don’t like the other guys laughing at them, there is nothing to stop them from wanting to be a big shot or a hero and popping me in the face. It was scary. I couldn’t let them see me sweat. I can watch the footage and see that I’m stuttering and shaking. But I’m not sure they can tell that. I really tried to man up for this one and be brave. And that was the stunt. The stunt was to roast them to their face. To hold them accountable for some of their crimes and some of their fashion crimes. Some of them had some really f–ked up tattoos and haircuts. [Laughs]

What was your most intimidating encounter?

My most intimidating encounter was probably talking to the white supremacists and the guys with swastikas on their bodies. To me, that is my kryptonite. I never really dealt with that before. I’ve been in Iraq and I’ve met guys who hate Jewish people. I even went to the Westboro Baptist Church once on Christmas and roasted those guys. But to be face-to-face with a guy who is wanting to put a swastika on his body and take his shirt off and be seen as that guy—to me, that was chilling. And it really tore at me, because as a comedian I wanted to go for it, but as a man—as a Jew—I was repulsed. I didn’t even want to entertain that guy. Why even give him that? But I thought about something that I heard Mel Brooks say one time. They were asking him why he would do The Producers, and all these Hitler jokes, why he would send up the Nazis. And he said, “It’s revenge through ridicule.” And the concept of revenge through ridicule struck me. It was like, don’t back off. Go for it! This isn’t a roast out of love. This is a roast out of purpose. I wanted to learn more. I wanted to take this guy down a little bit. I wanted to embarrass him. And I wanted to make my point that he’s an idiot.

You have that great line where you tell one of them that his swastika tattoo is supposed to be tilted.

I left that in for the history buffs. [Laughs]

Did you censor yourself at all from saying a really good joke? Like, “You know what? I enjoy living, so maybe I’ll just keep this one to myself”?

When you tell a guy he looks like a child and a child molester at the same time, no. I purposely did it like I was in a club or a theater. I really wanted to take the filter off and let it rip, and that itself was liberating.

You did two gigs for the male prisoners, and one for the female inmates. What were the biggest differences in those shows?

You think of jail and prison, and you think of guys. They know how to be institutionalized. They adapt. They’re working out. They look good. They had their tattoos on display and their hair braided and they were ready to go. But I feel like there is another piece of women that gets taken away when they go to jail. They don’t look the way they look on the outside. They looked a little sadder to me when I first walked out. They weren’t as hyped up until I started swinging the jokes. And once I did… I honestly feel like that might have been one of the more gratifying experiences of my career.

It was the night before the men’s show, so it was a way for me to warm up. I didn’t want to do my act—I wanted to just riff with them and entertain them and make them feel good. And it went both ways. I feel like we both got something out of it. I’d never done a show in jail at that point. I’d never done a show for all women at that point. And they really boosted my confidence as I maybe boosted theirs a little bit. I felt like I brought them out of the dumps a little bit, even in a more profound than with the men.

The couple times the show gets kind of sexual, to be honest with you, is in the women’s part. That’s when it got really kind of bawdy. And I didn’t have as much of a plan going into that show. That was a last-minute invite from the jailers to do the show for the women. Because I didn’t have a planned out act, I was able to go in there with my regular comedy-club swagger and just do it like a nightclub. That’s where I could just grab a woman’s hand and say, “Have you been in here long enough to find me attractive?” The woman who was holding her [pregnant] belly out, I asked her if she was stealing for two. To me, I felt like it was a huge release of tension. Wayne Dicky said a couple weeks later that morale was still buzzing, especially in the women’s dorm, where nobody had spoken to them as women in so long that it really lifted their spirits.

Did any of the inmates —or one of the guards— get you back and fire off something funny?

They creamed me but I edited all that out. [Laughs] No, I’m kidding…. Did they get me back? Yeah. There’s a little piece of it at the beginning. I’m like, “Please don’t shank me,” and they think it’s so funny that I’m worried about it. I always like when they throw it back at me a little bit. The women did that a little bit more than the guys. I don’t know if anybody got any big, witty zingers on me, but I have a feeling some of them are going be coming out of jail soon, and they’re going to be looking to get me back for the rest of our lives. [Laughs] That is a to-be-continued question.

Do murderers or violent criminals even deserve to be entertained by a gig like this?

This is a tough question and this is one I have struggled with. I feel like where there is no hope, there is no life. I feel like even somebody in jail has something to contribute, even if that’s just being kinder to the person in the next cell who is not a murderer and is coming out someday. It sounds corny but this is the one time in that jail where the Nazis, the Crips, the Hispanic gangs, the old guys, the young guys, the murderers, and the guys who are in there for nonviolent crimes—they’re all in the same room having a communal experience, laughing together, at themselves, at me, with the guards, and to me that serves a greater good than pointing to any one murderer and saying he doesn’t deserve to laugh…. To be able to make people feel good, even if they are damaged people, even if they are people that have done some mistakes, I still feel like they need some hope.

How have your views on prison changed from your experience down there? 

I learned inside every orange jumpsuit is a human being who needs to get their life back on track, who needs to get back to their family. Except maybe for those Nazis bastards. And that prison reform is something that is really, really important and going into the election season, I hope that this becomes an emergency. There’s so many people locked up for nonviolent crimes, they’re mixing with these violent people. That’s what really struck me. Solitary is torture. I got a little taste of that. There are way too many people locked up for things they shouldn’t be locked up for.

Give us a few tips for roasting inmates.

The first tip: There are no tips. It’s never been done because you should never do it. I could’ve been killed. If I had a family I wouldn’t have done it. They are the most dangerous people you could imagine.

Second tip: Make sure you take command of the room right away. When I started cracking on people, they were heckling from all sides. I had to let them know that I was in charge. I was like a lion tamer in a cage. The first thing I did was I went after the Nazis and wished them a happy Hanukkah.

Third tip: Make fun of the guards first. It’s something I learned from doing USO shows. If you make fun of the commanding officer, it’s something I call vicarious insubordination. Suddenly the guys are on my side because I’ve said what they are not allowed to say.

Fourth tip: Eat before you go. The food in jail is terrible. And I’ll quote a joke from the show, “I wouldn’t feed this food to a dog. Then again my dog never shot anybody during an armed robbery.”

Fifth tip: You have to look them right in the eye if you’re going to talk smack. I have a black belt in karate that I got when I was 10 and I always thought that gave me the confidence to talk smack the way that I do. But nothing could prepare me for this. Just animal instinct. Look ‘em in the eyes, let ‘em know you’re not afraid. But just in case, wear a cup and a diaper.

Who is left on your roasting bucket list?

I’m really strongly thinking about roasting the police next. It’s like: How do you do something even more dangerous?