In the event that I needed to stall for time, I’d brought along a small guitar and amp combo.7 So I decided to get the show started by playing overly animated heavy metal guitar solos, a skill I picked up in my lonely teen years. I’m not suggesting these guys were savage beasts or anything, but, not entirely ruling out that possibility, I figured a little music couldn’t hurt. And much to my relief, it actually seemed to work. By the time I stepped up to the microphone, the inmates appeared to be willing to hold off on shanking me or even hurting my feelings for at least a few minutes.
“I never thought I’d have the chance to say this, but it’s really great to be here in prison with all you guys,” I said to kick things off. I don’t normally like to cater to a specific audience when writing my material, but I decided to make an exception this time and come up with a set just for the guys at Sing Sing. Most of it had to do with whether or not I’d end up being anyone’s bitch should I ever wind up in prison. It was hard to make out exactly what they were saying amid all the clapping, laughing, and hollering, but the general consensus seemed to be that, if that ever did happen, I would be passed from cell to cell quicker than the latest issue of Juggs magazine. It was a little unsettling at first, but then the part of me that just wants to be loved more than anything else won out and I was flattered.
A lot.
“Who here is from out of town?” I asked the inmates once I got a bit more comfortable.
They seemed to enjoy that one.
“And who came from farthest away today?” I continued.
That line sort of confused them. As it turned out, most of the Sing Sing population hails from the New York City area. Still, they laughed politely until a guy in the front row slowly looked around, raised his arm, and yelled, “I’m from Kansas City!”
“So, did you always want to live on the East Coast?” I asked. “Or did it just work out that way?”
I thought I had hit it out of the park with that line, but instead of convulsing with laughter the inmates just groaned in unison while slumping in their chairs.
“I guess even violent felons have feelings,” I thought. “All right, noted.”
Despite that momentary bump in the road, I was having a really nice time in prison and decided to hand over the mic to Carl and Laura. Carl did a short set about his fictional workout regimen and the inmates ate it up, particularly after he decided to remove his shirt and blind them with his pasty flab.
Then it was Laura’s turn.
Being an entertainer and all, Laura decided to wear a lovely red dress to prison to enhance her already striking beauty, something the inmates seemed to appreciate a little more than she had anticipated. Her set was going well, but at some point she started to feel like one of those characters in a Bugs Bunny cartoon who turns into a giant lamb chop or turkey leg in front of some other character who hasn’t eaten in a really long time. Only she felt that way times three hundred.
“Thank you and good night!” Laura said, ending her set early as Big House vibes won out.
As Laura took shelter backstage where the inmates could no longer drool over her, a gargantuan corrections officer who had been assigned to prevent anyone from doing anything really prisony to us during our visit walked over to her.
“Are you okay?” he asked.
“Yeah.” Laura shrugged. “I guess I just got a little scared out there.”
“You know why you got scared, don’t you?” the officer asked.
“No. Why?” Laura asked hopefully, thinking the officer might perhaps offer her a little insight into the human psyche.
“See those guys out there?” the officer said, gesturing to my new buddies. “Those guys are all murderers and rapists.”
Laura didn’t appreciate his answer too much, but—having the emotional maturity of a fifteen-year-old and all—I sure got a kick out of it. Things were getting better by the second in prison as far as I was concerned. So, with Laura on close watch, I took the stage to wrap things up.
“Thanks for coming, guys,” I said. “And I just want you to know I think Sing Sing is the best prison ever!”
“You’re a fucking moron!” one of the inmates yelled in response.
“Is that you, Dad?” I shot back and immediately said good night. Go out on a high note, I figured.
To my sheer and unbridled delight, the inmates gave me a standing ovation before the officers began urging them back to their cells. And as we passed the cell blocks on our way back to the outside world, the sweet adulation continued.
“Dave! Dave! Dave!” they chanted in unison.
I’ll be the first to admit I sometimes seek approval in the wrong places, but it was still awesome. I felt like the lord of the fucking underworld.
Before we passed through the final set of prison doors, the warden handed me a copy of the poster used to advertise my show. It looked pretty much like a typical comedy show poster with the exception of one bold block of text in the corner that read “Must have one year clean disciplinary to attend.”
“Next time let’s make it one month clean disciplinary!” I told him. “I wanna pack the place!”
He just looked at me after that, so I decided to focus back on all that clapping and cheering in the distance as we headed back to our car. I couldn’t get enough of it, so I made sure to keep a leisurely pace.
“Would you come on?” Laura groaned at me. “I wanna get out of here.”
“Look, just because you’re not having a good time in prison doesn’t mean I have to be miserable, too!” I scolded her before basking in the adoration of my Big House buddies some more. I felt like Tim Robbins in The Shawshank Redemption only I couldn’t wait to come back.
“See you next year, Dave!” one of the inmates called out to me from his cell window, waving between the bars.
“Yup, see you next year,” I thought, waving back. “I guess I’ll just go do whatever the fuck I want now.”
It was hard not to consider how wildly the inmates’ lives and mine were about to diverge after all the good times we had just had together.
As we drove back to New York City, I was beaming. I had not only come out of that prison alive and unviolated but had actually managed to put on a show that everyone in attendance (other than Laura) seemed to really enjoy. But what was even more striking to me were the aftereffects of my visit to Sing Sing in the weeks that followed. My day-to-day anxiety seemed to be cut in half and I felt almost calm in situations that might have otherwise sent me into a panic. I didn’t suddenly fancy myself some sort of tough guy or doer of good deeds or anything like that. It was more like the anticipation of performing in front of a few hundred violent felons had built up so much pressure inside me that I busted some sort of emotional gasket by actually going through with it. And with that pressure gone, I could suddenly breathe easy, walk with a more confident stride, and not freak out about everyday life so much. All of a sudden someone’s overly loud headphones on the subway weren’t quite so grating and those televisions some asshole chose to install in the back of every New York City cab weren’t as annoying. I even found I could accept McDonald’s completely unpredictable and seemingly arbitrary removal of the McRib from their menu as just a part of life.
I was almost embarrassed to bring up this newfound state of well-being to my therapist when I saw him the week after the show.
“They say prison changes you, but could four or five hours be- hind bars really count?” I wondered.
“You took a trip to the underworld,” he said after squinting at me for a couple of minutes. “And it sounds like you had a really nice time.”
It seemed so simple, but I had to agree with the guy. I did have a really nice time. And if I can have a really nice time in a room full of murderers, rapists, and other negative types, well, I reasoned, I can probably have a really nice time just about anywhere. In fact, part of me keeps wondering if spending even more time in prison, like maybe a few weeks or months, might have an even more positive effect on me.
