Tasteful Nudes: ...and Other Misguided Attempts at Personal Growth and Validation (27 page)

“Sing Sing Correctional Facility,” a voice on the other end grunted after a couple rings.

“Hello,” I said. “I’d like to speak to the comedy booker.”

The line got quiet. As it turned out, Sing Sing didn’t have a comedy booker. Undaunted, I pressed on and, after a few seconds of hushed conversation on the other end, was connected with the “deputy of programs.”

“Hi, this is Dave Hill … from show business,” I said.

“Of course, Dave!” the deputy replied. “How can I help you today?”

“I’d like to come up there and give your inmates the show of a lifetime!”
2

After a few minutes of back and forth, I succeeded in booking myself a show at Sing Sing, a place I was determined to make every bit as fun as its name suggests, if only for a little while. I had hoped the deputy would have just said, “How soon can you get here?” But apparently they had a pretty action-packed schedule already and the show had to be slated for about six weeks out. It was a little frustrating, but I was still thrilled and immediately called Carl and Clark to tell them the good news.

“Sing Sing here I come!” I screamed.

Carl and Clark seemed just as excited about things as I was and, just as I had hoped, found my booking a show in a prison even funnier than our hypothetical conversation the night before.

“This is the greatest thing ever!” Carl said. “You’ll be killed instantly!”

“I know!” I laughed. “I know!”

In the weeks leading up to my Sing Sing debut, Carl, Clark, and I found the idea of me going to prison to be increasingly funny every time we discussed it. We even told all our friends about it, and it was funny every time then, too. About a week before my prison debut, when the reality of my situation finally kicked in, I suddenly didn’t find it quite as funny anymore. Instead, it seemed more like some sort of horrible prank I was inexplicably about to play on myself.

“What’s to stop a murderer who’s behind bars for life from killing again, maybe even just to break up the day a little bit?” I wondered.

I came up empty.

“I’m a dead man,” I moaned to myself.

Suddenly, all I could think about were the innumerable ways my show could go horribly wrong. I saw myself bombing, with microphone feedback filling the airspace where I’d hoped laughter would go. A lone inmate would approach the stage, slow-clapping at me before removing a shank
3
from his waistband and driving it straight through my ribs, causing the inmates to laugh for the first time of the night. Then he’d call all his friends over to take turns shanking me, playing soccer with my head, calling me names, and having sex with my face. As I faded in and out of consciousness, I’d make eye contact with a corrections officer standing just a few feet away.

“Sorry, buddy,” his eyes would say. “I got a wife and kids and six weeks until I reach my pension—you’re on your own. Oh, and you need to work on your comedic timing.”

In the week leading up to the show, I watched this movie in my mind repeatedly. Sometimes I’d see it from my own perspective and sometimes I’d see it on one of those grainy security camera monitors I’d seen on those cable television prison shows.

“An auditorium full of furious and violent felons is no laughing matter,” the narrator would say. “Funnyman Dave Hill found out the hard way.”

Then they’d zoom in and freeze on my face and add some dramatic piano music to let the viewer know that I was pretty much the deadest guy ever.

There were no two ways about it—I had to get out of this mess. To that end, I decided I would simply write an e-mail to the deputy at Sing Sing explaining that, as it turned out, I had been implanted with a baboon heart at birth and—while it had served me well for most of my life—it was now acting up and if I didn’t have surgery on it right away, I’d be dead by the weekend, which meant that I regretfully had no choice but to cancel the show. I’d even throw in something about how upset I was that I couldn’t just head on over to prison immediately after surgery because my uptight cardiothoracic surgeon was being a total dick about it.

Just as I was about to compose that e-mail, however, I saw there was another e-mail already waiting for me in my inbox. It was from the deputy at Sing Sing.

“I was just checking in to see if you were all set for your big show next week,” the deputy wrote. “The inmates are
so
excited to see you.”

“‘
So
excited to see me’?” I thought. “What the hell is that supposed to mean?”

And then I remembered: when I arranged the show, the deputy had asked me to send him a photo of myself so he could make a poster to hang around the prison. I had intentionally sent him the most effeminate looking photo of myself
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I could find because I thought that would be just one more funny thing in this whole scenario. And maybe it was, for a time, but now the men of Sing Sing knew exactly what I looked like. And, since convicts are historically irritable people and some of them might have been getting out soon, I realized I had no choice but to accept my fate.

This flyer helped convince three hundred Sing Sing inmates to come to my comedy show instead of whatever else might have been going on that night in prison. I was pumped.

“I’m really looking forward to coming,” I wrote back to the deputy, tears gathering in the corners of my eyes. “Oh, and, you know, just so I might better prepare myself, can you tell me exactly what sort of guys are ‘
so
excited to see me’?”

“So far about two hundred and fifty inmates have signed up for your show,” the deputy later replied. “They are all maximum-security violent felons and they really like jokes about being in jail. They will no doubt be your ‘toughest’ crowd.” Then, just to fuck with me, he put in one of those smiley face emoticons.

“That sick bastard!” I thought before slamming my laptop shut.

Despite my constant terror in the week prior, when the day of the show finally arrived, a sort of peaceful resolve washed over me, kind of like how the death row inmates always seem on those cable prison shows I was just talking about. Sure, I might get shanked or made someone’s bitch but—dammit—these guys were gonna get one hell of a show!

“Maybe I can just pretend I’m Bob Hope doing a USO show, only instead of soldiers I’ll be performing for murderers, rapists, and other guys who hate rules,” I thought. “Everything will be just fine.”

I had originally planned to head up to Sing Sing alone, but in the end I decided to bring Carl, Clark, and my friend Laura with me. If anything actually did go horribly wrong, I wanted someone to be able to tell my story. And since Carl and Laura were comedians, too, I had the option to push them on stage at any moment if I got too lonely out there by myself.

To help get into the spirit of things, on the drive up we took turns reading aloud from a dictionary of prison slang I’d found on the Internet. As it turned out, they have fun words for just about everything in prison. There was, of course, “keister,” a verb meaning to hide something in your ass, and “eye fucking,” which means to stare at someone aggressively for much longer than he’d normally be comfortable with. “Feed the warden” means to use a toilet,
5
“jack shack” refers to the cell of a frequent masturbator, and “quit swinging on these nuts” is what you might say to someone who is being a sycophant.
6
But our hands-down favorite was “fifi,” a fun word used to describe an artificial vagina made from a hand towel, a plastic bag, some hand lotion, a few rubberbands, and, presumably, lots and lots of tears.

Sing Sing itself occupies a stretch of land along the banks of the Hudson River that would likely be prime real estate if it weren’t for its current residents. As soon as we pulled onto the grounds, a corrections officer rolled up to us in an unmarked van.

“Hi.” I gulped. “We’re here to do a comedy show.”

The corrections officer stared at us blankly for a few seconds before directing us to the main entrance on the other side of the building. As we pulled away, he shook his head in the way those weary townspeople always do in horror movies after they’ve just reluctantly given directions to that wooded area where all those people were mysteriously killed that one summer to a carload of wayward and oversexed youth who think they’re gonna live forever.

After parking the car, we nervously made our way through Sing Sing’s massive front doors, where we were met by a handful of surprisingly upbeat corrections officers who guided us through airport-level security procedures. Unfortunately, they made us ditch the cameras we’d hoped to use to take all sorts of really fun “Let me outta here!” pictures to show friends and family around Thanksgiving and other holiday gatherings. Once we finally proved we weren’t trying to smuggle in one of those birthday cakes with the big file baked inside, we finally received hand stamps visible only under the ultraviolet lights that hung beside each of the gates that separated the inmates from freedom.

“No glow, no go!” the corrections officer bellowed not-so-jokingly as he pounded our hands with the stamp a bit harder than seemed necessary.

Apparently, the otherwise invisible stamps are used to prevent inmates from doing that thing that always happens in movies where someone clubs some other guy over the head with a pillowcase full of loose change, drags him into a supply closet, strips him naked, changes into his clothes, and then walks out of prison like he was just visiting or something. In light of this, I made a mental note not to wash my hands too aggressively at any point during our visit so I wouldn’t end up dating someone named Rollo by the end of the day.

As we passed through the ancient and ominous brick and steel corridors on the way to the auditorium where the show would be taking place, I felt as if we were suddenly in some old prison movie.

“This is so cool!” I said to the corrections officer leading the way.

He didn’t seem to agree, so I decided to just keep my mouth shut and stop pretending I was James Cagney in the role of Cody Jarrett, the ruthless, deranged leader of a criminal gang who winds up behind bars in the movie
White Heat
, something I was really enjoying but whatever.

When we arrived at the auditorium, a small sign at the entrance announced that my show would preempt that week’s movie night, a screening of
How to Lose Friends & Alienate People
.

“No biggie,” I thought. “ These guys probably know plenty about that subject already.”

Shortly after we got settled backstage, the inmates began to file in. And as much as I’d promised myself I wouldn’t, I still found myself trying to guess what each guy did to wind up there.

“The guy with the mustache and glasses looks kind of rapey,” I thought. “And that guy over there with the shaved head and hairy knuckles? Strangler all the way. A bit stabby, too, I guess.”

Still others looked like they just might be into dumping bodies into a river or maybe setting buildings on fire while people they didn’t like all that much were still inside. As their numbers grew, however, it became hard to focus on any of that stuff. Before long, they just seemed like a bunch of guys who all happen to work out a lot, have the exact same taste in clothes, and like to get face tattoos when the mood strikes. There ended up being about three hundred inmates in attendance, which—being in show business and all—I was happy to see.

“Maybe that sexy poster wasn’t such a bad idea after all,” I thought.

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!”