the most handsome boy in that school,” she told me. “That is her problem, not yours.” I was thinking,
Ma, I’ve got a mirror, I know that’s not true
. But if your mom isn’t your biggest fan then you are kind of fucked.
Anyway, it didn’t help matters that I was deathly afraid of the dentist. Sometimes I outright refused to go. If anyone put their hands in my mouth I would gag. But my freshman year in college, as I was gaining more confidence in school and working at the radio station and thinking about the life I might have once I escaped Long Island, I decided it was time to get my yellow teeth capped.
The experience was brutal. I thrashed and gagged and struggled. And that was just when they put the bib on me. When the dentist finally came in and saw what was happening he exhibited exactly the kind of empathy I’d become used to all my life: He told me to calm down and grow up. I was so shocked, I did.
After that dreadful, scary, painful experience, I swore off going to the dentist again. I couldn’t do it. I was just too scared. A year went by, then two, and three. I might have gone once or twice before graduating from college, but when I started working I never bothered. It didn’t matter how much Howard made fun of my teeth or my breath or any combination of how they worked together. I wasn’t going. And it turned into an issue. My gums became badly infected and my teeth were in really bad shape. Underneath the caps my teeth were literally rotting, like something out of eighteenth-century England.
My teeth, how big they were, how bright they were, how much they resembled a horse’s, became a constant topic of conversation on the show, along with my deathly fear of dentists. By the time I had been working with Howard for a couple of years, it had been close to six years since I had sat in a dentist’s chair. My mouth was killing me, but I could not bring myself to make an appointment.
One afternoon in 1987, I went to a graduation party for one of our interns at her parents’ house. One of the intern’s uncles walked up to me and introduced himself. He said his namewas Charles Randolph and that he was a big fan of the show. He also happened to be a dentist. “I know what you’ve said on the air about dentists,” he said. “But you’ve got to see someone. Come by my office. I promise I will make you comfortable.”
Of course that phrase—“I promise I’ll make you comfortable”—sounds creepy now, but I immediately liked and trusted him. And even I knew caps didn’t last forever, especially if you never bother going to the dentist. So I resolved to see Dr. Randolph and have them replaced.
But it wasn’t that easy. After years of neglect, my gums were so bad I needed several appointments and treatments to clean them up. Naturally, when it was finally time to take care of the caps, it couldn’t be a private moment between me and Dr. Randolph. It was a part of the show. Only this time, it was going to be videotaped.
It was the winter of 1988 and Howard had decided to do our first pay-per-view special, called
Howard Stern’s Negligee and Underpants Party
. It was the early days of pay-per-view on cable. There were still plenty of places around the country that weren’t wired for cable. People were getting excited and ordering the special. The numbers coming in were astounding. We started hearing about fans who had plans to drive for miles just to get to a town that was wired, so they could book motel rooms for viewing parties. It became one of the highest-grossing premium specials of the time.
We did a Lesbian Dial-a-Date segment and had Dweezil and Moon Unit Zappa on as guests. Vinnie Mazzeo lit his underwear on fire and then cooked an egg. And they filmed me at the dentist getting my teeth capped. Unfortunately, the show ran long, so most of Vinnie’s bit and all of mine got cut from the special. That’s when Howard had a brilliant idea: Let’s sell a videotape of the show and
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