I Went to a Texas Jail to Roast the Inmates


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? …

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.” …

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.'” …

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’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…

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…

As I left, I realized just how lucky I am to be “outside in the free” as one inmate put it…

5 thoughts on “I Went to a Texas Jail to Roast the Inmates

  1. This is an unbelievable story.
    I almost didn’t read it because of the headline.
    It’s overwhelming to think about the size of the current American inmate population, and worse how cut off they are from the world and the basic mental health services so many of them require.

    Liked by 1 person

    • Not only that, but the drug war is so racist, that most of the people who get caught up in the criminal justice system are black and Latino. And for minorities, finding and affording mental health services is a lot harder, which means that our prisons have basically become their healthcare system.

      Thanks for reading. 🙂


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