Comedian Jeff Ross isn’t afraid of taking his comedy to some dangerous places. As the Roastmaster General of the Comedy Central celebrity roast series, he has thrown jabs at former heavyweight champion Mike Tyson (On Tyson’s facial tattoo: “What is that, a target for pepper spray?”), hurled barbs at billionaire blowhard and Presidential candidate Donald Trump (“Trump and I have a lot in common…we both fantasize about his daughter.”) and put down perpetually prepubescent popstar Justin Bieber (“I know you’ll never end up like Kurt Cobain or Amy Winehouse. Respected.”).
But it’s not just zinging powerful celebrities with shocking subject matter that attracts Ross, it’s also performing comedy in dangerous situations. Ross has performed stand-up for U.S. troops in the middle of Iraqi warzones and, in his most recent special, roasted inmates live at the Brazos County Jail in Texas.
Jeff Ross Roasts Criminals: Live at Brazos County Jail is more than just a stand-up special showcasing Ross’ razor-sharp wit, it’s also a documentary about the state of the American prison system. Ross personifies the plight of the American prisoner by hanging out with inmates, talking with them, eating with them, interviewing them and, of course, roasting them. By making light of a bad situation like the overcrowding of prisons, Ross has shed some light on one of the darkest problems plaguing the United States. It’s deep, it’s thought provoking and it’s totally hilarious. Which is exactly what Ross was aiming for.
We called the Roastmaster at his home in LA and talked about everything from politics and pot smoking to the prison system and his next project.
Mike Andrelczyk: You’ve done comedy in some pretty dangerous places, like Iraq and the Brazos County Jail. What draws you to places like that for comedy?
Jeff Ross: I think it goes back to my childhood. Just trying to make my mom laugh when she was sick in the hospital. There’s a real gratifying feeling when you make someone laugh who’s had a hard time. In essence, the sadder the situation, the more comedy can heal and make people feel better. That’s really what I’m after in those situations.
MA: How did the idea for the prison special come about?
JR: I wanted to do something meaningful and provocative. I wanted to do something dangerous. I wanted it to be different. I didn’t want to do just another stand-up special. I thought, “let me take on a big subject,” and I thought “Crime in America,” there’s so much there. We’re a violent country. We’re obsessed with bad guys. As I researched it, I realized I had to personify it and roast people so I would get reaction shots. And criminals personify crime in America, so I thought, “let me just go to a jail, where no other comedian would go.” It took a long time to get permission and get access but I’m really glad it did, because I feel like it was important to shine a light on these people.
MA: You talk openly about smoking pot and having a medical marijuana card. What was it like to meet people behind bars for marijuana charges?
JR: I just felt like it was a lot of luck involved. I smoked pot before it was legal and I didn’t get in trouble and other people sell it or smoke it and they got in trouble. I felt lucky.
MA: Comedy is a great place to start a dialogue on issues like this. In America, it seems like we look to comedians like John Stewart and Stephen Colbert to help us form our political opinions. Why do you think that is?
JR: First of all, it goes down easier. All the bad news, when it’s filtered down through a comedic lens, is easier to accept and hear and deal with. And second of all, I think people open up to comedians. I think comedians have access that maybe even journalists don’t have sometimes. We get the real human nature of it all. People trust comedians for some reason. We’re sort of modern-day journalists.
MA: Have you noticed a dialogue open up about prison and drug laws after your special aired?
JR: It was very popular. The numbers of people who watched it on TV and have downloaded it have been massive. I think it helped make it a more accessible thing to talk about. I noticed that shortly after it aired, the President went and visited inmates in jail and shortly after that the Pope went and did that. And those were two things that really helped shine a light on prison reform and minimum drug sentencing and solitary confinement and the death penalty. And I feel like maybe in some small way, or maybe even in a big way, I helped make that a more accessible conversation and make it cool to go see people that are locked up.
MA: Do you think that Trump has an actual shot at becoming President?
JR: As a comedian, I hope so, because it’s so good for comedy. There are so many good jokes and I’ll be doing them all at my show. It’s all turned into a reality show. America is so disillusioned with our leaders that we’re making a mockery of it as a way to rebel. It’s like the newest reality show – “America’s Next Top President.”
MA: What do you think of Hillary Clinton?
JR: Love her. I hope she does well. I want to bang her on the desk of the White House one day. I want to be the First Lover. I want to be the Secretary of Lovemaking.
MA: I heard a rumor that Kanye West is going to be the next person to get roasted on Comedy Central? Is that true?
JR: No, it’s not true – at least not yet. If more people like you put it out there, maybe he’ll accept one day. I think he would love it and his wife has a great sense of humor. Anything’s possible. You wouldn’t have believed James Franco or Beiber would’ve agreed, but they did.
MA: Your roasts always have some really, really funny appearances by non-comedians.
JR: We need non-comedians to spice it up. I don’t want to just make fun of my peers. I want to make fun of Martha Stewart and Mike Tyson and Snoop Dogg and Shaq and other people who add a lot of variety to the roast. That’s important, so in order to make them look good, we have to write for them and let them find their comedic voice as well. It’s a lot of work, but the goal as a producer is to have everybody come off well.
MA: Who’s been your favorite non-comedian to perform at a roast?
JR: I love Snoop Dogg. I feel like Snoop could’ve easily become a comedian if he’d have chosen that path. I think he’s just remarkably witty, funny and fast. He’s so great.
MA: What projects do you have coming up?
JR: For my next roast I want to roast a police precinct. I think that could be really cool. The cops kind of need that community outreach right now. And maybe just shine a light on what’s happening inside those police headquarters right now. Things need to be shaken up and looked at a little bit.
Jeff Ross performs at the Pullo Center in York on November 7. Get more information and purchase tickets here.