I Went to a Texas Jail to Roast the Inmates; Here's What I Learned About Incarceration in America

06/12/2015 08:48 am ET | Updated Jun 12, 2016

I recently roasted the inmates at a maximum-security jail in Texas. It was an intense and rare experience. No other jail or prison in America had the guts to let me in -- not even in my native state of New Jersey. So when some brave men wearing white cowboy hats agreed to let this wise-cracking yankee come down there and insult the inmates, I was salivating. I'd been wanting to do something different, a new adventure. Criminals fascinate me. What are they really like? Why do they keep returning to jail in such large numbers? Do they and the guards have a sense of humor about their situation? Being a comic is like having a backstage pass to the world. But this wasn't a rock concert or awards show -- this was a jail in Texas, where they take law enforcement as seriously as I take roasting.

To prepare for my shows, I went down a few days early and talked to the inmates and the officers, tried the food and shot some hoops. I met a few really despicable people, but I also met some guys that deserve a second chance. Not everybody in jail is a bad person. Some are desperate. Some are crazy. Some are innocent. I even visited the "Shu" -- a tiny rubber room. This is where people who act up are sent to "calm down." Being in the "Shu" means having zero human interaction for indefinite periods of time; if you're in there, you have to defecate through a hole in the floor. But, enough about my dressing room.

I admit I roasted these people for sheer entertainment purposes -- but also to get myself a glimpse into the American prison system. It's broken. We say we're a free country but we lock up more people than anywhere else on Earth. Almost two MILLION American children have a parent locked up right now. We have more jails and prisons in America than colleges and universities. All this is still hard for me to comprehend. What's happening in this country? Wayne Dicky, the jail administrator who proudly allowed me access to his facility, told me that American jails are de facto mental health facilities. Back in the seventies many psychiatric hospitals were shut down. Now all those people needing mental help wind up in jail instead. I freely walked around the cells and dorms and saw the insanity first hand. We tuck so many damaged people away and forget about them -- like human dust. One admitted drug addict told me he's come back to jail thirty-six different times just to "get clean." When I hear stories like that, it's no wonder the recitivicsim rates are so high.

For security reasons, I did two separate shows just for the guys. They were great crowds. No walkouts. I wrote an act specifically for them, "I bet some of you are locked up for possession of less marijuana than I have in my lungs right now." They roared. They were on my side. As I rallied them I also polled them, "Where my murderers at?" Three guys near the front raised their hands. I stepped back a little. "Where my innocent people at?" A hundred hands flew up. "Where my guilty people at?" Ten hands raised. "How many of you lied so much you don't even know the truth anymore?" Everybody laughed. Even the guards. Even the Nazis. In fact, in order to come to my show, each inmate had to behave for a month.

I invited the accused on stage with no restrictions. Anyone who wanted to approach the stage and get speed-roasted was allowed up. Ten guys surrounded me. I nervously stuttered as I busted their balls. I told one chubby twenty-something guy who was admittedly violent that he is, "One of those rare people who looks like a child and a child molester at the same time." After firing off a slew of slurs, I finally broke it down with an inked up Hispanic guy named "Insane" about his baby daughter. I asked him what he'd say to her right now if he could. He said, "I'd tell her 'I miss her. Daddy be home soon.'" Even the white supremacists got a little choked up.

Brazos County Jail has about 600 male inmates and about 150 women. The men and women don't mix. So I couldn't resist a last minute invitation to perform for the ladies. I walked in, took hold of a woman's hand and asked, "Have any of you been in here long enough to find me attractive?" I did the whole show impromptu with my regular comedy club swagger. I asked a woman in the front row holding her belly if she was, "stealing for two?" These orange clad ladies laughed so hard with their whole bodies. They flailed their arms wildly and leaped out of their seats every time I landed a good one. They rolled with it even better than the guys and even I was laughing at their candid comebacks.

I'll never forget Big Mama Joe, Country, and a young funny lady who pulled out her ID and revealed her actual last name was "Hooker." A woman named Shayna claimed to be locked up for stealing baby formula. I called her out for what sounded like a phony story, but for that one particular moment, the truth was secondary. I just wanted to make her laugh. I was acting on a challenge to myself as a comedian -- to bring laughs where there are none. Doing that cheers me up too.

Weeks later, Wayne Dicky, the jail administrator, told me morale was still very high among his inmates, especially the women. He said, nobody had talked to them "as women" in a long time. Maybe my visit made his jailing job a little easier. But not for long. Recently, a male Brazos inmate awaiting trial for murder was found dead. This is unfortunate -- and very tough for the psyche of the guards, nurses, and administrators. It's a part of their responsibility to keep people alive. Babysitting bad guys is a thankless job.

As I left, I realized just how lucky I am to be "outside in the free" as one inmate put it. I've done some dumb stuff in my life -- but I've never been seriously busted. I've only been taken in twice. Once in high school for staying out after town curfew so I could go to The Rocky Horror Picture Show, and once because I put a toy gun up to another comic's head at a college student center and a near-sighted cop thought it was real, took me down and put his gun to the back of my head. I was arrested for inciting a riot and cuffed to a desk for a few humiliating hours. Luckily, my lawyer, the late great roaster Greg Geraldo, came with me to court and got the whole thing dismissed. I also sold some weed towards the end of high school, but luckily I never got busted.

I don't know if I would have survived incarceration. It's really scary inside those walls. Young first offenders get thrown in for something small and non-violent, but once they're dropped into a den of hardened criminals it's hard to stay clean. You almost have to become a criminal to live amongst them. And remember, 90 percent of the people who go to jail are eventually released back into our world. "Hello, neighbor!"

I am grateful to the staff and officers of Brazos County Jail for this chance to go inside and do what I do and learn a little along the way. I can now tell you first hand that jail sucks. But inside every orange jumpsuit is a real person who needs to get their life back on track. Except maybe those Nazi bastards. Anyway, I'm just happy to be in the free and off on my next adventure. Soon I'll attempt my most dangerous show yet... I want to roast the police. Any takers?