Jeff Ross Goes to Prison

With a title like “The Roastmaster General,” it’s tempting to simply think of Jeff Ross as a quick-witted, calloused, insult slinger. While those labels all certainly apply, Ross’ new special, Jeff Ross Roasts Criminals: Live at Brazos County Jail (which airs on Comedy Central Saturday, June 13 at 11:00 p.m. ET/PT), offers a different look at the veteran standup as he spends several days interacting with and entertaining the inmates of a Texas detention center. The special blends roast footage with a documentary style behind-the-scenes look at the daily lives of the jail’s inmates and staff, resulting in a truly insightful and comedically tragic look at the American prison system. I talked to Ross about his motives for creating the special, the lessons he learned, and the questions we should all be asking about incarceration in America.

The new special… holy shit. I expected it to be funny, but it also had a lot of heart. There was a real human interest side to it. You laid out some hard facts about the American prison system, while at the same time, showing a lot of respect to the incarcerated. You punch up at the institution, instead of punching down at the prisoners. What made you want to do a project like this?

It was all a natural journey. It wasn’t planned – as you said so well – in a way that was punching up or punching down. I went in there with a general curiosity for American criminals. Why are they there? Who are they? Do they laugh at themselves? These were honest questions I would get from watching jail movies, lockup shows, COPS, all that stuff. I was curious and a little afraid. I wanted to confront that and do the most provocative roast I’ve ever done. I wasn’t thinking about the inmates as human beings. They were like some strange class of subhumans. My thinking was very antiquated. It wasn’t until I actually got into the jail and met people – like you said, heart – when I learned about who they actually were. I saw that there are good people. Some of them are total scumbags, but some of them deserve a second chance. Some of them acted out of desperation. Some of them shouldn’t be in a maximum security jail. Some of them just sold some weed, stuff like that. There are first time offenders, non-violent. It’s jail that makes them violent. That was really upsetting to me. I saw myself in that. I thought, “I’ve sold weed. That could’ve been me.” I don’t know if I would’ve survived jail, to be honest.

When you talked to the prisoners off-stage, it showed in your face, posture, and eyes that you were really feeling for these people. A lot of this felt like a documentary. It was interesting watching the footage of you interacting with them and the administration, then juxtaposing that with standup.

I spoke to one of the administrators a few days ago and he told me that someone did indeed die there last week. That really weighs on them. One thing I learned is how challenging their jobs as detention officers are. They’re charged with keeping these people alive. When somebody dies in custody, it’s crushing to the staff at the jail. I have a lot sympathy for them. I have a lot of respect for them, not just for keeping me alive, but for keeping themselves sane.

Speaking of sanity, another statistic that was brought up was that the American prison system is providing more mental health care service to people in this country than actual hospitals.

It’s dumbfounding. It’s hard to believe. We have a lot of crazy people, who need a lot of help and yet, we don’t have the infrastructure to take care of them. So, they go to jail to sober up, get out of harm’s way, or out from under the bridge where they’re living. The jailers are challenged with taking care of them. It’s no easy task.

I read that you had been turned down by some 150 jails before landing on Brazos. How did this become the one?

They said yes. (Laughs) It’s kind of the same way we find the people we roast on Comedy Central: we ask hundreds and finally someone goes, “All right, I’ll do it.” I feel like this jail was very brave. The head administrator took a very big risk letting a comedian come in like this. This is not something that has ever been done in a lockup. He’s proud of his staff and his facility and I think he wanted to show that jails don’t have to be Gulags. They can be run by civil-minded, forward-thinking people, even in Texas, where they take incarceration as seriously as I take roasting.

How long were you there?

About four days.

Did you have any issues while you were there? Any situations where you felt like you were in some kind of danger?

I don’t know if I would call it imminent danger. But I walked freely among the cells and inmates. There are no guns inside there to protect me. There are only a couple of officers at any given time. So, yeah, I think there is always danger. You always have to have your eyes wide open at any time. To be honest with you, if I had a family, I probably wouldn’t have done it. There’s nothing to stop someone from wanting to be a big shot and punch me in the face, or bite my ear off.

It didn’t seem like you pulled many punches. Was there anything that you were instructed not to talk about?

There were many things I was told I couldn’t talk about, but as you saw, I did it anyway. They didn’t want a lot of provocative, sexual material.

You blew that out of the water.

Everything about jail sucks, but there’s no sex allowed. To not bring up those kind of issues is a little crazy. I couldn’t help it. It’s a fascinating thought that these people are locked up without any kind of companionship. It all came out. Comedy comes from pain and I didn’t want to be subtle. There’s no subtlety in a jail cell. I just went for it.

Throughout the special you bring up a lot of good points about the prison system. The prisoners got it. They’re living it every day. But what feedback did you get from the administration?

To their credit, they let me be me. They gave me freedom of speech, which I was really grateful for. I’m sure the jailers have seen my act before. But Sheriff Kirk and the administrator, Wayne Dicky… I think they understood that being a comedian is about the mind always being unfiltered. They gave me that. They didn’t censor me or reprimand me. I’m grateful for that. There are two audiences for this show: the people inside the jail and the everyone else in the world who is going to watch it. I had to be funny, not just to the inmates, but to everyone watching on TV. I wanted people watching to say, “Man, jail sucks. I’d better think twice before I make a stupid choice in my life.” I didn’t want to beat around the bush. I wanted to make that clear.

When you open up the special, you say that there are three things that you want to focus on, based on your fascination with criminals: what are they really like, why are they there, and do they have a sense of humor about their situation? Do you feel like you adequately answered all of those questions?

I don’t know if I adequately… it’s a great question that you’re asking right now. I think asking questions is the goal. From my own personal observations and things that came up in the show… I think I’m still processing the answers to those questions. But I think they’re open-ended questions. I don’t want to find the answers in my show. I want everyone to start asking the questions themselves. This should be a huge campaigning point. This should be something that the candidates are forced to address: prison reform. I don’t have all of the answers, but someone needs to be asking the questions. I didn’t want this to be a political special. I wanted it to be about the people. Once you see how sad and desperate some of the people are, you can’t help but ask these questions.

Photo by Bob Levey.

Jeff Ross Goes to Prison