There are two public sides to stand-up comedian Jeff Ross.
There’s the “Roastmaster General” who takes on a different disguise each year for the Comedy Central roasts, turning the event into his own personal Halloween full of tricks and treats. For the Comedy Central Roast of Rob Lowe that aired this Labor Day, Ross put on a wig and dressed in purple like the late musical legend Prince. Garish. Loud. Crude and rude.
Then there’s the guy who is loyal to his family, his Friars Club, and genuinely cares about the people he teases.
It’s this latter Ross who has emerged over the past couple of years, deserving your attention and truly carving out a place for himself as something more than your basic insult comic. Last year, he went into Brazos County Jail to learn how Texas inmates survive behind bars, and then to lift their spirits while still putting them in their place. This year, he shipped up to Boston, where the police commissioner – himself a likable cartoonish character out of a 1930s gangster film – invited Ross to ride along with his cops first, then perform for them at a BPD charity benefit.
“I have the best job in the world. I make fun of people for a living. And I think the reason I can get away with roasting my way through life is because it comes from a place of love. I love everybody. Even the one group of people that nobody seems to love right now: Cops.”
We open on Ross at the benefit, punishing the police force first with a pun: “You’re under a roast!” Then adding: “Next I want to attempt my most dangerous roast ever, roasting an audience of armed policemen.”
Of course, his endeavor isn’t quite so dangerous once he has spent quality time with several of the officers in the crowd.
But it’s more than a roast, anyhow, and definitely special. Comedy Central even bills Jeff Ross Roasts Cops as such: “a one-hour special combining documentary filmmaking, stand-up comedy and investigative journalism.”
Ross bookends the hour with footage from New York City: a Black Lives Matter protest at the start, and an NYPD funeral procession at the finish.
“What the hell is going on between the cops and our communities?! This is a national emergency. People are dying on both sides. And nobody is talking to one another,” Ross says.
No other major police department responded to his call to sit down and talk, or joke. Conveniently or coincidentally, Ross went to college at Boston University, and BPD’s Commissioner William Evans welcomed Ross openly. Why? “I want to break the stereotype out there that we’re the bad guys,” Evans tells Ross. “We don’t mind you making fun of us because I want the people to know we’re real people.” It helps that their city police force apparently hasn’t shot an unarmed suspect in more than two decades, as Ross notes later from the stage.
In his cap and mustache, Ross certainly looks the part of a grizzled veteran cop, although he’s put through a hazing fit only for a rookie or a snitch.
The officers and the police union initially wasn’t so keen on Ross roasting them, as footage from the NYC protest (including Ross talking with Quentin Tarantino, and a photo of Ross with fellow comedians Ed Larson and Ted Alexandro with a “Black Lives Matter” sign) made its way to Boston before he did. So the union issued a bulletin instructing officers “not to engage with this gentleman,” illustrated most harshly when Ross first lobs joking insults at a handful of officers in a precinct house conference room. The officers stand along the back wall, stone-faced. Ross’s jokes die miserable deaths.
Thankfully for all parties involved, the Boston Police commissioner sets Ross up with several ridealongs with his officers so Ross can learn that Blue Lives Matter and so the cops themselves can begin to trust Ross.
Two officers suggest Ross buy lunch for the precinct, and the ensuing pizza party does allow their fellow colleagues in blue to warm up to the blue comedian. Another officer partnership clues Ross in to racial politics, offers their outside opinions on the death of Freddie Gray in a Baltimore police van, and recalls their experiences during and after the Boston Marathon bombing. An officer named Darren tells Ross that city residents treated cops very well for the next few weeks, “but it got uncomfortable. We liked it better when people called us assholes.” A plainclothes duo gets out of their car with Ross to engage with and joke with a group of young black men on the sidewalk. And a meeting with police academy graduates lets Ross know that BPD has no problems recruiting gay officers.
Ross sprinkles the humor throughout the hour, one-liners here and there when he can with individual officers, then a few minutes at a time from the charity benefit itself — culminating with a Ross trademark, inviting volunteers onstage for personalized barbs.
In the end, he closes with a joke that even a cop can love to hate, yet still double over at in laughter.
Jeff Ross Roasts Cops premiered on Sept. 10, 2016, and can be viewed online and via the Comedy Central app. It’s also available for download via Amazon and iTunes here: