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Jeff Ross Roasts Criminals: How the Roastmaster General Broke New Ground

Sonia Gumuchian |
June 18, 2015 | 9:15 p.m. PDT

Staff Reporter

Jeff Ross roasting prisoners (Twitter/ @realjeffreyross)
Jeff Ross roasting prisoners (Twitter/ @realjeffreyross)

Though you may know insult-comedian Jeff Ross from stealing the show at practically every celebrity roast (didn't think we'd forget this gem, did you?), in the past couple years, Mr. Ross has also published a best-selling book, released numerous comedy specials, hosted "The Burn" and most recently, premiered a Comedy Central special shot in a maximum security jail in Texas. 

Ross and his team approached many jails around the country, but Brazos County Jail was the only instituition that not only accepted the comedian's offer to perform, but even used his show as a way to encourage its prisoners to behave for a month leading up to the event. 

It's quite an impressive task to take on, as any moment from this special could be seen as a potentially disasterous. At least for the viewers at home accustomed to such shows as "Orange is the New Black" and "Oz," it wouldn't be surprising for any punchline to start a physical altercation that could harm his crew or Ross himself. Even though (spoiler alert) Jeff Ross came out of it fine, the tension throughout the piece is definitley something to incite viewer interest.

However, even with the clever one-liners and brilliant moments, Jeff Ross the comedian, gave Jeff Ross the social commentator his time on stage as he used this special to touch on disturbing facts on the U.S. prison system and point out its hypocracies and ridiculous inconsistencies. After every couple of jokes, the audience had an opportunity to be informed on how 2.5 million children have had at least one parent in prison, and 40 percent of prisoners return within three years of their release. 

Even though Ross admitted to having an absurd amount of marijuana in his lungs, many prisoners in Brazos County were caught with minor drug offenses that, even though considered criminal in Texas, would have made them legally profitable in other States. 

So why is Ross such a great fit for this ambitious performance? Simple. He burns himself first before he attacks anyone else. It's quite a masterful and humbling technique, as the first thing Ross asked as he entered the women's prison was "Have you been here long enough to find me attractive?" Hilarious and tactful, that opener not only provides a way to break the ice, but also lets Ross take a punch at himself before he begins throwing it at others. No one is safe from depracation, not even the performer.

Like most popular comedians−even the harshest ones—Ross posseses a touch of vulnerability and (even though this wouldn't be the first word to describe him) endearment. There's no denying having his troubled past come into play helps strengthen his connection to his audience. Knowing about his tough childhood helps one appreiciate his comedy even further, especially since it came from a tragic place. If Jeff Ross can get through difficult circumstances, maybe these prisoners can too. 

He even mentions during the special how his poor choices could have led him to incarceration if he wasn't so lucky. Relating to his audience of mostly first-time non-violent offenders, Ross insists he believes in second chances. Especially with 90 percent of prisoners in Brazos County Jail eventually getting released back into society. It's beneficial, to say the least, to help integrate these men and women back into normalized life. Laughter seems like a pretty good start. 

Ross had a goal to do something "purposeful with his comedy," and through his groundbreaking special, he accomplished just that. 

Reach Staff Reporter Sonia Gumuchian here. Follow her on Twitter here



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