At the beginning of his latest TV special, “Jeff Ross Roasts Cops,” Ross is standing onstage at Laugh Boston in front of an audience of city police officers, including Commissioner William Evans. “I have a theory why cops love doughnuts so much,” he says, straight-faced. “ ’Cause they look like they’ve been shot.”
It’s a corny joke, but pointed, too, given the killings by police officers that gave rise to the Black Lives Matter movement. When the camera scans the audience at the roast, one officer is slapping a table and laughing. Someone groans in the background. “This is for real; my safety’s off tonight,” says Ross.
Roasting cops for an audience of cops would be a daunting task in ideal circumstances, much less in the current climate of heightened tensions between civilians and police. But Ross, who roasted inmates at a prison last year, “jumped at [the idea] because everybody’s been talking about them,” he says, speaking by phone. “Nobody’s been talking with them.”
Ross walks a careful line in the special, which airs Saturday at 11 p.m. on Comedy Central, between his sympathies for the victims of police brutality and for the police themselves. They are real people with names and histories.
Ross says he wanted to do this roast for the police, to humanize them and show how difficult their job is. “I love everybody,” he says at the beginning of the special, speaking directly to the camera, “even the one group of people that nobody seems to love right now — cops.”
But moments later in the special, his conflicted feelings are clear when a Black Lives Matter rally passes by his house and he interviews some of the participants, including a black man who says that when he sees a police officer, he looks around for witnesses in case something happens. Some of the protesters carry signs that read “Which Side Are You On?”
“I feel like I’m on both sides and I always was,” says Ross. “It’s the individual stories and voices that you tend to side with. And sometimes that’s a cop and sometimes it’s not. So yeah, it was emotional. I think I’ve never been more relieved to be done with a project. Yet it feels far from finished because there’s so many more questions than answers with cops in America right now.”
Ross sent requests to take part in the special to about 30 big-city police departments, but his only positive response was from the Boston Police Department. Commissioner Evans had not heard of Ross — “I’m not a big Comedy Central guy,” he says — but he did his research and was intrigued by how “Jeff Ross Roasts Criminals” humanized some of the inmates in that earlier special.
“When we had conversations with Jeff and he explained how his whole idea was to explain the human side of police officers, and with everything going on in this country, I thought it was a good opportunity,” Evans says. “And that’s what we’re continually trying to do out in the community, is make people aware that we’re not bad guys.”
When Ross finally got to Boston, the roast was on precarious footing. In a cringe-worthy scene in the special, Ross tests out some of his material at an afternoon roll call as a few dozen officers stare him down. “I’ve never performed in front of an entire room full of YouTube celebrities before,” Ross jokes to complete silence.
“Let’s be honest, if Whitey Bulger’s name had been Blacky Bulger, they would have caught him a lot quicker,” he tries, getting a smattering of laughs. The jokes were blunt, but Ross thinks the bigger problem was a memo he found on a station bulletin board labeling him as anti-cop for attending a Black Lives Matter rally. The memo — which he shows in the special — is in response to his request to ride along with the Boston police, and it encourages detectives to steer clear of a comic “who apparently believes our profession is best suited as a punch line.”
Ross says the scene after he bombed at the roll call was somber, and could have been the end of the project. “Everybody left,” he says. “It was just my crew and I. And we had a real talk about what to do. I don’t think we ever said, ‘Let’s bail,’ but it definitely crossed all our minds.” What made him keep going, in part, was the jokes.
“At the end of day I’m there doing comedy, and the show must go on,” he says. “I hate wasted jokes. I wanted to tell those jokes. I wanted to get them out there, even if they didn’t like them. The idea that they weren’t receptive was sad, but it wasn’t gonna stop me.”
In the special, Ross spends less time onstage than out in the field or in a break room at a police station, busting the chops of officers late into the night over pizza. There are sequences showing police interacting with the community, helping children, or laughing with an intoxicated man before sending him on his way. But in one of the ride-along sequences, Ross asks a black officer and a white officer about the racial dynamics of working together, and provocative questions about the Freddie Gray case, in which a Baltimore man died while in police custody.
“I was just genuinely curious about race,” says Ross. “What’s it like for a black cop and a white cop driving around together? What do they think about some of the bigger cases that Americans are looking at right now?” They were questions he never expected to have answered, but he gets some frank responses. “I built a trust by driving around for eight or nine hours with these people. And they opened up. I either earned their trust or wore them out — maybe a little bit of both.”
Ross’s follow-up projects, hosting Comedy Central’s “Roast of Rob Lowe” and the Oddball Comedy Festival tour, lightened his mood. “It was the easiest transition ever,” he says, “because it was such a relief to take the heaviness of policing and set it aside for a week or two and do something that was just pure fun.” (The Oddball tour comes to the Xfinity Center in Mansfield Friday, though Ross will not be on the bill for that show.)
Still, Ross would like to keep digging into controversial topics in future roasts. “I’m in a place in my life right now where I want to do more than entertain,” he says. “I want to learn as I’m going. I also want to, I don’t know if ‘teach’ is the right word, but enlighten my audience, who wouldn’t normally be talking about this subject. That’s the fun part.”
Jeff Ross Roasts Cops
On Comedy Central, Saturday at 11 p.m.
Nick A. Zaino III can be reached at nick@nickzaino.