Comedian Jeff Ross Talks Roasting Boston Cops for New Special on Conan

Unlike Peyton Manning, comedian Jeff Ross is a master at roasting people, which is why he’s testing his skills against one of the hardest audiences possible for his new special.

The Roastmaster General and Boston University alum stopped by Conan on Wednesday night to chat with the late-night host about his experience roasting the Boston Police Department for his latest Comedy Central show. Ross told O’Brien that he wanted to take on the challenge because he feels that, while everyone is talking about cops in America, no one has been “engaging with them.”

“I asked all the big cities if they would let me come do ride alongs and do a show and roasts cops to their face to see what their job’s really like, to see what they’re really like,” he said. “I thought if I made fun of them, will they laugh or will they want to kill me too? I think the answer is a little bit of both.”

Ross revealed that he was turned down by every other department around the country, “except one place, and that’s the city of Boston.” The comic praised Police Commissioner William Evans for letting him do the special, as well as for his approach to policing.

“An unarmed person hasn’t been shot and killed by the Boston cops in 25 years,” Ross said. “It’s all about community policing up there. They know the environment that they live in. The cops live and work in the community. They work where they live, which I think helps to.”

Although his main goal for the special was to start a dialogue between people and the police, Ross also wanted to show off the human side of officers by seeing if they could take a joke.

The comedian admitted to O’Brien that a few myths about officers are actually true.

“They’re way fatter than you ever would think. Cops love food more than anything in the world,” Ross said. “The job’s so intense, but there’s a lot of waiting around. They have to be on call to do who knows what. There’s a lot of kind of sitting around and they carb up.”

Check out a clip from Ross’s chat with O’Brien above.