Jeff Ross on Roasting Boston Cops, Black Lives Matter, and Tom Brady Jokes

Photo by Amy Zvi

From Justin Bieber to Donald Trump, Jeff Ross has made a career out of roasting celebrities. These days, though, the comedian and Boston University alum is turning his attention to more serious topics, which is why he decided to attend a Black Lives Matter rally and roast police officers for his new Comedy Central special. Surprisingly, the Boston Police Department was the only force in the country willing to be the butt of Ross’s jokes. Ahead, the Roastmaster General opens up about the experience, what he learned from Commissioner William Evans, and why it’s probably a bad idea to mock Tom Brady around the BPD.

It took a while for the Boston Police Department to get on board with your jokes, and they definitely hated the ones about Tom Brady.

I had a feeling I would instigate them right out of the gate. And I did. That’s the one thing I noticed Boston cops are sensitive about. You can say anything, race, police brutality. You can make jokes about almost anything and they laugh—even doughnuts. But when you get to Tom Brady, they really did ice me out.

He was probably joking, but it was odd to hear that one cop say he’d cover up a murder for Brady during your ride along session.

I’m sorry, I don’t think he was kidding. His name’s Danny and if Tom Brady ever does anything wrong, I would find Danny and he could be a major suspect in the cover up.

Before they let you do the roast, initially, the police union labeled you as a cop hater for attending a Black Lives Matter rally.

That was really surprising. I was shocked and I thought they should’ve been embarrassed. That’s shoddy information and bad detective work on their part. All they had to do was ask me. But they profiled me and that hurt. It’s a terrible feeling to be misrepresented or to be labeled anything. I wasn’t trying to take sides, I was trying to learn from both sides talking. When they push you away and say, “You’re on that side, get away from us,” it sort of discouraged me. But I had a show to finish and I didn’t want to give up.

Doesn’t that experience get at the heart of the issue, which is people on both sides labeling each other as entirely bad, when it’s more nuanced than that?

We’re living in a labely world. We’re living in a hashtag environment. Which side are you on? That’s the opening question to the show. That’s not something I asked, that’s something that the Black Lives Matter rally was asking the people there. And it’s sort of that way on both sides. Nobody really is receptive to the other side’s message because there’s blood involved. When there’s blood involved, obviously emotions are high. It’s always the loudest voices that get heard. I started talking to the softer voices, the more reasonable, open-minded voices on both sides. I happen to think that Commissioner Evans is one of those people. He’s soft spoken, but he makes sense.

The special highlights how the BPD hasn’t killed an unarmed civilian in 25 years. What’s working here that departments around the country should adopt?

I think community policing is the key, which is what Commissioner Evans taught me about. Getting out of the car. Getting out of your comfort zone as a cop. Going face to face with the people on the street so that when they see you they, recognize you. When you see them, you recognize them. There’s a familiarity.

After going to the Black Lives Matter protest, what do you think police officers can learn by taking the time to listen to their concerns?

If a cop took the uniform off and a protester put the sign or megaphone down, they’re twins. They’re laughing at the same stuff. They’re from the same neighborhood. They know the same people. So, are you a cop first or are you a human being first? I think part of the problem is some are cops first. I don’t think that’s best. I think we have to remember our humanity and look at each other and talk to each other and hug, shake hands. It’s so simple. My cousins were going through a family crisis. There was death. There was drinking. It was ugly. I said, “Just wake up every morning and acknowledge each other’s humanity.” Give them a hug. Say how are you. You don’t have to be best friends. You don’t have to be pals. But just acknowledge each other. I think cops can learn that from those protesters. A little bit of compassion goes a long way.

Looking at the world at large, do you think the biggest problem today is just a serious lack of empathy by people for their fellow man?

I do. I absolutely do. Everything is so cut and dry. Social media is so mean. The tabloids are outing everybody’s indiscretions. We all have our crosses to bear and we can’t forget that. Nobody’s perfect. As a matter of fact, it’s the people who claim that they’re perfect that are the ones getting in trouble because they’re hypocrites. And we’re so tough on each other. I think comedy is good in that it helps us laugh at ourselves. It kind of does bring people together because I found in my jail roast that Mexican gang members still laugh at the same jokes that the white supremacists were laughing at. I was like, wow, that’s a connection. It’s sort of a weird connection, but it worked. They both laughed at the same joke about the jail food, or Kim Kardashian, or whatever it was. I do think comedy and what you’re talking about, empathy, they go hand in hand.

‘Jeff Ross Roasts Cops’ premieres on Comedy Central Saturday, September 10, at 11 p.m.

This interview has been edited and condensed.