Celebrity Roast Master Jeff Ross's Latest Victim: The Police

Comedy is hard. Every comic has tricks to make it easier, whether memorizing recycled crowd-work that you can make "seem fresh" on a moment's notice, or just getting shitfaced. Not Jeff Ross, who seems to be trying to make comedy as hard as possible. Why else would he choose to do a comedy special for the Boston Police Department, about the Boston Police Department?

Ross, sometimes known as the "Roastmaster General" for his numerous appearances in Comedy Central's Roasts, usually targets media ghouls like Ann Coulter and Flavor Flav. Now he's setting his sights on a slightly different group—cops. We spoke to Ross about his latest special and why now is the perfect time to roast the police.

This interview has been edited for length and clarity.

VICE: I really enjoyed the special—but on paper, it sounds insane. How did you turn this "roast of cops" into a reality?
Jeff Ross: Well, my last special was at a jail. I thought it'd be funny to roast prisoners, humanize the prisoners. And then I thought, who needs that right now? And my friend Jonas at Comedy Central said, "How 'bout cops?" And I took a beat, and I was like, you know, you have to follow that discomfort. One of my producers, Stu Miller, told me that, and he got that from Jon Stewart. I started writing acts about cops, and jokes that not just cops might laugh at, but we would laugh at as the general audience.

On your first ride along, you said something to the effect of, "You gotta laugh at this shit or else you'll cry." That seems to be sort of the thesis of the special.
That statement—"If you don't laugh at this, you'll cry"—that was something that just happened organically in the middle of the night after I found myself laughing both at and with the cops when they were dealing with a homeless, potentially mentally ill, drunk person. My only alternative was to stop filming and sulk and wonder where mankind went wrong, so I just kept trying to ask more questions and build material.

Do you think comedy has helped you—and America in general—deal with the horrible bullshit we're constantly bombarded by in the news?
We've heard this, "laughter's the best medicine," our whole lives, but once something finally gets close to you, or something sad happens, or you're in the middle of a national tragedy, or you're looking at footage of boys being murdered by law enforcement… You have to escape. And I think that's why roasting's become so popular, because it's hard. It's authentic. Everyone's crying about what's happening between cops and the communities that they police right now, but I don't hear a lot of conversation between the two, and I think that's kind of what my special's about.

One of the funniest moments to me was your first appearance at the Boston Police Department, because someone circulated a memo about you being a cop hater. You were telling really funny jokes, but you were bombing. What was going through your head at that moment?
It's funny… I had such a hard time editing that scene. I felt like I was watching my own nightmare. I remember right afterward, sitting down in that empty room. Everyone was gone, and I sat that with my manager and my producers, and we just all had different ridiculous theories of what had happened. Turns out none of us were right. The cops were just mad at me.

To me, it says a lot about the real problem that police in general are unable to take any criticism from civilians. But then you sat with them, and they did warm up to you, even though you were criticizing them. How did you get them to ease up on you?
Did they ease up on me? [Laughs] I got funnier, and I brought them to an environment more conducive to having fun—a charity event for kids with cancer. I think they were inclined to have a little more fun, even though they weren't drinking, they were still off the beat, off the street. I think by doing that, sticking with it after that first colossal bomb, I earned some respect.

In your special, you mentioned that the Boston Police Department hasn't killed an unarmed person in 25 years. What do you think makes them better than other departments?
They have terrible aim.

[Laughs]
God, I wish I had that joke a couple weeks ago when I was doing the show. That would've been a showstopper. Damn you, VICE! Honestly, I think that's probably a better question for the commissioner. Part of it is community policing, part of it's training, and the guys and gals that I met were not aggressive people.

Right, and the cops you met were very diverse.
I was pleasantly surprised to see the Boston Police department was like that—22 percent African American. That makes it easier for me as a comic. They got a little bit of everything, so I got something to work with here. It's kinda fascinating how the job still appeals to so many people of different ethnicities. I got hassled for cutting through Washington Square Park a few weeks ago by a Chinese cop and an African American cop. Even though they were total assholes, I was kinda glad they weren't just other white guys hassling me.

You had a TV crew with a bunch of cameras, and people definitely do act differently in front of the cameras. So how do you think normal people, without a TV crew, can get cops to listen to them?
Be white.

[Laughs]
Try to remember that cops are almost only exclusively dealing with shitty people, so if you're a good person, come at them extra kind and extra polite. Especially right now. There was a cop shot in the calf when I was in Boston, so everyone was on edge. They never know who's armed. As I'm saying this, I'm in traffic and I'm watching a motorcycle cop talk to a black dude, and they're just laughing and having a good time. God knows what they're talking about, but more of that. People are just screaming at the cops right now, and I'm not saying they're wrong, but getting louder isn't really helping with anything. Sometimes it's getting more thoughtful. I'm talking about everyday interactions with cops. You talk about arrests and brutality, what's going on with African Americans, that's another story. I'm not black, I'm never gonna understand that part of it. But I'm doing everything I can as a US citizen to try to understand.

You ended the special by saying, "The real cops need to step up and leave the fake ones behind." How can we help them do that?
I think we need to press for transparency and reform, and we need to really take a good look at who's getting hired. I think body cams are a good idea, even though a lot of cops resist. People are really scared, and people are dying, so I feel like the cops are gonna have to bend over backward to earn everyone's trust right now.

I remember years ago, the president had a "beer summit" after a police incident with [Henry Louis Gates Jr.], a black college professor. I'd love to see the president, or the most open minds on both sides of this issue, get together and start talking instead of preaching to the choir. It can't go on like this. This is not a sustainable situation right now. Everyone seems to be suffering.

Do you think people can help more with their local police departments?
Yes. As a matter of fact, once a month in my neighborhood of New York, there's a meeting in a church basement with the head of a local precinct, and whoever wants to come. They give you a little update on the neighborhood, and then people ask questions. Sometimes it goes a half hour; sometimes it goes a couple hours. But it's great theater, it's normally very friendly, and it's a great time to be heard. Maybe it starts there. A lot of communities do these sorts of meetings, but average citizens aren't interested. They're not going to that; they don't even know about it. I was trying to dig in [for the comedy special], so I started going, and I kind of got hooked on it. There are citizens who also help with organizing it all, and they put up signs around the neighborhood. But I'd like to see something more formal. I'd like to see a summit or a convention. You know, "Cop Con."

Where you get to cosplay as Rodney King?
You're in. I'll moderate.

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Watch Ross's special, Jeff Ross Roasts Cops, airs on September 10 at 11 PM on Comedy Central.