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Jeff Ross Moves Beyond Celebrities And Brilliantly Roasts Criminals in Prison

Jeff Ross Moves Beyond Celebrities And Brilliantly Roasts Criminals in Prison: Robert H. Levey

Robert H. Levey

Last night, like many times before, Comedy Central aired a roast with roastmaster general Jeff Ross lighting up a room. But unlike any of those other times, this audience was made up entirely of prisoners.

Jeff Ross Roasts Criminals: Live from Brazos County Prison is one hell of an idea. It’s by no means a traditional roast—obviously—but instead a mishmash of Ross’ characteristics. The special documents Ross’s three-day stint of chatting up, roasting, and playing to both male and female inmates. As a whole, the special carries what feels like an understanding of the situation, that it can be simultaneously observed as serious, ridiculous, and hilarious.

“I worked with really smart producers,” Ross told Esquire. “I talked to ex-cons and placement job advocacy groups for preparation for the jail show. That’s what brought it to a new light for me.”

But while comparisons to Johnny Cash’s At Folsom Prison have come—it was inevitable—the inspiration wasn’t some kindling of outlaw spirits or what have you.

“It was only later that I felt a certain compassion for the inmates,” said Ross. “It was really more of a cavalier attitude that brought me to jail. I wanted to roast criminals. I thought it’d be fun!”

Landing on the particular jail was a long ordeal. Ross and team called a good many beforehand, all of which were reluctant to house cameras or comics. But one detention center in Brazos County, Texas, had the curious idea to “vet” the audience (or as much as you can with an all-criminal crowd). In order to gain access to the show, inmates had to behave for a month.

This made for surprisingly great, enthusiastic crowds, said Ross. “Even the meanest jokes got laughs.”

In one clip, where Ross performs for an all-female, all-orange-jumpsuit audience, you see his balance of being in the zone as a fish out of water. Ross cracks, “One guy, 50 female prisoners. This is like the first scene of every porno I’ve ever seen. I should be delivering a pizza right now.”

“There was this controlled chaos,” said Ross. “The prison had never had that many inmates in the same room at the same time, which is very precarious for them.”

But it sure seems the great experiment worked.

A few more jokes/burns from the special:

“You look like what happens when the morning-after pill kind of works.”

“An eye for an eye a tooth for a tooth. Some of you look like you’ve given more than others.”

“You’re one of those rare people who looks like a child and a child molester at the same time.”

“Wait, are you guys laughing extra loud because somebody’s trying to build a tunnel right now?”

“The good thing about a jail show is, nobody gets up and walks out.”

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