Ann Coulter found out what it was like to bomb as a stand-up comedian on this past week’s Roast of Rob Lowe. But the mild reception she faced was nothing compared to the deafening silence that greeted comedian Jeff Ross when he decided to roast members of the Boston police department.

As Ross tells viewers in his new Comedy Central special, Jeff Ross Roasts Cops, which premieres this Saturday night at 11 p.m., Boston was only police force that responded when he inquired about bringing his brand of insult comedy to a big city police department. When Ross asks Commissioner William Evans what made him agree to the unusual premise, he tells the comedian he wants to “break the stereotype out there that we’re the bad guys.”

But if the commissioner wanted regular Americans to see that police officers can have senses of humor about themselves, the scene upon Ross’s first arrival failed to make that case.

Ross says all he wanted to do was “give them a few laughs before they hit the streets,” but when he walks into their afternoon roll call, the officers stand stoically around the perimeter of the room, refusing to even sit down in the chairs provided.

The comedian, wearing a Boston PD T-shirt, begins by thanking his audience and saying he’s “never performed in front of a room of YouTube celebrities before.” When that joke is met with blank stares, he pivots, referencing the city’s “rich criminal history,” from Whitey Bulger to Tom Brady. At least that joke gets a response, even if it is an angry groan.

“Holy shit, that sucked. Hasn’t there been enough bombing in Boston?” Ross asks viewers after apparently cutting the session short. If the cops didn’t like the jokes he told to their faces, it’s a good thing he saved that one for his voiceover narration.

Ross only finds out later that before he spoke to the officers, the city’s police union sent out a bulletin that labeled him a “cop hater” because he once attended the same Black Lives Matter rally that made Quentin Tarantino an enemy of police unions late last year. It was that experience, talking to mostly black people who believe cops are the enemy, that made him want to find a way to “humanize” them in the first place.

Ross finds a much more receptive audience later on when he performs for Boston police officers in a comedy club setting, drinks and all, at a benefit for the department. There’s a reason he decided to open the special with a scene from that set, in which he gets genuine laughs for saying he named his penis Rodney King “because I beat it so much.” Clips from that performance recur throughout the hour-long show, but even there he at one point has to tell the audience that it’s OK for them to laugh. “You don’t have the right to remain silent,” he jokes.

Unsurprisingly, Ross gets the most laughs when he moves away from systemic problems with policing and makes things personal. This is especially true when he brings the commissioner onstage and commends him for letting underprivileged kids cut his hair and when he puts on a bodycam and speed-roasts a series of officers. Sample joke to a male bike cop: “Does that, after a few hours, start to hurt your vagina?”

He also gets them to agree to let him strap on a bulletproof vest and join two officers for a ride-along, during which the three of them end up getting roasted by a drunk man on the street. “You’ve got to laugh at this shit, or else you’ll cry,” Ross says, as he finally starts to find some common ground with the cops. In a separate ride-along, another pair of cops defend the Baltimore officers who were charged with and ultimately acquitted of killing Freddie Gray. They find it “inconceivable” that the cops there would intentionally try to seriously hurt or kill a detainee.

Ross’ latest special serves in some ways as a companion piece to 2015’s Jeff Ross Roasts Criminals, in which he traveled to Texas’ Brazos County Jail and made fun of convicts to their faces. He entered that situation with similar levels of both curiosity and trepidation, but the men he met in jail were generally more willing to laugh at themselves than the Boston cops are. Perhaps they just felt they had less to lose.

“Being a comedian is like having backstage pass to the world. People will open up to us, because we’re not journalists,” Ross told Chelsea Handler, who has produced similar documentary-style specials, on her Netflix talk show this past week. “As comedians, we have a responsibility to shine a light on the darkest things in the world.”

Those who know Ross only from shows like the Roast of Rob Lowe, which represented Comedy Central at its most frivolous, might find that statement a bit overblown. But while Ross is perfectly capable of dressing as Prince and making fun of Ann Coulter, it is in specials like this that he has found a way to use comedy as a tool to force people to actually listen to each other.

The jokes themselves are no less outrageous, but by moving the spotlight from celebrities to cops, who are at the center of one of the biggest problems facing America right now, Ross has the potential to make people see this issue of police violence in a new light. And he somehow manages to do it all without sacrificing the dick jokes.