Is it all right to tell you that I miss you terribly?" the woman asked. It was a few weeks ago, the Christmas season, and I was waiting for my lunch with a friend at Claire's. The woman had approached our table tentatively, yet she spoke without any hesitation whatsoever.

"Sure it is," I told her. "And, hey, can I borrow twenty dollars?"

After a laugh, she proceeded to share that she had listened to me on the air at KC101 during my entire run in mornings, from 1997 through 2004.

She seemed to remember every move I'd made. When I drank a girlfriend's bathwater on the air, it had caused a fight between her and her then-boyfriend, who was evidently not very passionate. When I mooned Dixwell Avenue in protest over a grade-schooler who was suspended for mooning a classmate, she went twenty minutes out of her way in an effort to catch a glimpse. And when I brought a cup of my semen to Radio Towers Park for a co-worker considering artificial insemination, she listened while her shocked colleagues ranted about there being "something wrong with me."

Then, after checking her watch, plus realizing that her mention of semen may have ruined my friend's appetite for the couscous he'd ordered, she said she'd leave us alone. But before going, she demurely asked for a hug. I stood up to give it, and she gave me an unexpected peck on the cheek.

"It's not exactly twenty dollars," she grinned.

"It's better," I told her.

She began to walk away, and there was that feeling again. That weird feeling you get when you do morning radio, as complete strangers become like relatives when you run into them on the street, in restaurants, at bars. It is a warm, fuzzy feeling, as if all sorts of people have your back in a crowded room, even while you're wondering if the person you are actually out with would be half so loyal. It's not scary the way some people seem to think it is, these strangers knowing your birthday and your child's name and what you did last Friday night. It's oddly comforting, even validating, and not in a ratings sense at all, but more in a "Maybe I'm not the freak I grew up thinking I was" kinda way.

She turned back to wave, no doubt thinking to herself that she'd never see or speak with or hear from me again.

"You coulda thrown in some tongue," I yelled.

It all started back in 1996. I was 29 years old, a freelance music writer for Hit Parader and Circus , two rock magazines that I'd grown up reading, and also for the Connecticut Post . On a good month I made enough money to go to Friendly's once; on a bad month...well, no Friendly's.

I had a sweet burgundy Camaro (I repeat, burgundy --not red), friends who were getting married and buying houses, and family members who whispered about me as soon as I left the room.

For extra money I drove for a local medical lab, picking up and delivering stool samples and pap smears. While I am proud to say I did have the best route, the fact that there was a cooler full of human refuse in the back of the car I was driving was not lost on me. I'd had dreams of being a writer since I was six, and here I was waiting in the lobbies of area old-age homes while seniors "tried to go" in the bathrooms down the hall.

(On one occasion an old woman took so long with her urine sample that I spilled it as I was rushing out of there. Rather than wait for her to work up another one, I simply filled the cup myself. I've often wondered what they made of the marijuana in her system.)

Ironically enough, my friends were trying to talk me into becoming a DJ. But their version of a DJ was not the kind I would eventually become; theirs was the guy at your wedding who acts like he made up the Electric Slide and imitates a cross between Wolfman Jack and Barry White when he announces the father-daughter dance. Eventually, a car salesman who works for a dealer who advertises on pretty much every radio station in the state bypassed the wedding and school-dance DJ notion altogether--on my behalf, he went right for the local big leagues: KC101 and WPLR.

First I met with the general manager of KC101, as they call WKCI, New Haven's Top 40 station. I went in armed with a briefcase full of press clippings. I'd always nodded politely whenever my friends suggested I become a DJ, knowing full well that there was much more to it than simply loving music. I figured I would meet with the GM, show my writing, and hope that at the end of the day I could get plugged in as a copywriter of some sort.

I never even got to set up my meeting at WPLR, as to my surprise I was immediately put on the air at WKCI's sister station, WELI. By week's end I was doing live reports from events like the annual Arts & Ideas Festival, fumbling my way through sixty-second call-ins whose high points included the mime performance schedule and how much red hots were going for at the closest cart.

None of my friends or family thought it would lead anywhere spectacular, but it was fun, and I was sometimes on within the same fifteen-minute span as "The Coach" George DeMaio, well known to anyone who grew up in New Haven or East Haven in the '80s. That was huge.
It didn't take long for me to realize that there was no way anyone at the station could actually prove that I was really at these events, or was even close to questioning it, so I began making my calls into the radio station from home. I'd be kicking back on my front porch, eating Bar-B-Q potato chips and petting my late schnauzer, Cruiser, as I extolled the virtues of, say, the yearly carnival at Long Wharf. For all I knew, there could have been a knifing that resulted in the entire carnival being roped off by New Haven police, but there I was, actually making statements like, "What a beautiful night to make a memory!"

With this newfound relaxation came some off-the-cuff riffing, and with that came KC101.
Glenn Beck was doing the morning show at the time, and he was already on his third co-host. There is a wariness that comes with that; a man can rotate girlfriends and not feel like he's developing a bad reputation, but rotating co-hosts definitely gets people thinking that there's got to be something wrong with you , which may not be the case. It's about chemistry, gelling, yin/yang--all that stuff.

I sat in with Beck and we clicked. You know when you do. You just do. It's not up to the general manager or the program director, and to a certain extent not even the listeners, to decide; the people doing the show know. Beck and I were off and running just like that, and I can honestly say that that period of time, from 1997 to 1999, with a sorely underrated local radio talent named Matt Feduzi doing news for us, was the best of my life.

Not too far into it, Beck, who had already been doing radio for over fifteen years, began talking syndication. Not necessarily syndication of the show we were doing, but syndication in general, as a means of survival. With the onset of Prophet, a computer system that allows producers to program songs, ads, and news breaks--thus eliminating any real need for DJs--and with the coming of the internet and satellite radio, Beck was convinced that getting syndicated was the only way to ensure still having a job in radio in the years to come. Glenn left in late 1999, and today the Glenn Beck Program can be heard in over 100 markets (locally, on WELI from nine to noon on weekdays).

Clear Channel Communications, the media giant that owns KC101, could have easily piped in a show from out of state--just as the now-defunct Hartford alternative rock station Radio 104 did with Dee Snider's replacement, Bubba the Love Sponge. But it was maintained that a small market like New Haven would be best served by someone actually from the area. That would be me.

And over the years, as I had women strip for Ricky Martin tickets, as I had women call in to talk dirty to me in a game aptly called "Make It Move," as I chatted up a hermaphrodite (asking the important questions, like "Which bathroom do you use?" and "Have you ever wanted to put yourself in yourself?"), it was my knowledge of the Elm City--my love of it--that would always be my saving grace.

By the time co-host number three came along (incidentally, I have incredibly fond personal memories of all of my co-hosts), I had become really interested in pushing the envelope.

I shaved my pubic region live on the air from the men's room.
I wore a feminine hygiene pad for one entire show "to see what all the fuss was about."
I played the actual birth of my daughter on the air.
I performed the marriage of two lesbians beneath a ridiculous billboard in East Haven.
I am quite proud to say that I always found Connecticut residents to be interested and, what's more, responsive to my envelope-pushing. The "conservative" rap that the people of this state are stuck with is crap, the "prude" label unwarranted.

Not that I never pushed past people's limits. My second day on the air, we were discussing an old movie theater being razed, and I commented, "It's about time. That theater's so old, after one movie in those seats you've got spina bifida." The next day--my third day on the air, my third day in morning radio --a woman was waiting for me in the lobby with a baby suffering from it. She made me hold the child while she schooled me on the subject.

Some people would later attribute my need to push the envelope to my being on the Howard Stern Show a few times throughout 2001, even though half of the things mentioned above predated those appearances. If Stern had an effect on me, it wasn't for the reason one might think, but because one of my times on the air with Stern happened to be September 11, 2001. Seeing the response he got from his listeners, their dependence on his updates, their trust , coupled with the sentiment everyone carried beyond 9/11, which is simply that time is precious and you have to be proud of what you do with it and make the most of it, I did begin to view this awesome job I had differently. From that point on, I felt like every moment on the air should either make you cry or make you pee in your pants laughing. I guess you could say that, one way or another, there had to be fluid as a result.

Enter Janet's boob. In the wake of Justin Timberlake exposing Janet Jackson's breast during last year's Super Bowl halftime show, radio was, more than ever, under a microscope. Traveling beneath the radar became a mantra.

By then, the number-one thing I was fascinated with was my one-year-old daughter. Most of my rants began to involve what I was learning about women from her, and from parenthood, which I thoroughly enjoyed exploring on the air--though some long-time listeners would accuse me of softening, of selling out. Before long, what were once raucous, hard-drinking appearances on behalf of the show, appearances in which I would perform songs I'd written with titles like "Slut in Misquamicut" and "You Don't Belong In A Thong," were replaced by Barnes & Noble appearances with me reading children's lit I'd written--stories like "The Adventures of Gassie," about a flatulent collie who saves the day.

But the crowds were there for both Vinnies, and being able to switch gears, to explore two very different levels of comedy, was incredibly rewarding. And I had a new outlet for my over-the-top sex stuff: stand-up comedy. A performance this past November with the local troupe Extreme Comedy proved yet again that Connecticut residents are up for getting crazy: there were two sold-out shows, chock full of young ladies hooting and hollering as I went on about things like golden showers, ordering sex toys over the phone, and so forth.

Now, almost eight years after literally falling into radio, the medium is changing in all the ways it was predicted that it would. Prophet--the computer system that allows producers to program songs, ads, and newsbreaks--has succeeded in terminating lots of radio positions; radio on the internet is taking off--Connecticut's own Ultra Radio, for instance; and satellite...well, everyone knows what's going on with satellite. Just ask Howard Stern, who is moving to satellite radio next year. Subscription only.

In my opinion, however, this just means there are that many more potential outlets for the radio personality, that many more vehicles. And each different playing field simply must distinguish itself from the other. If one outlet allows the talent to use profanity and really go for it, logic dictates that another will have to become significantly safer.

My last program director at KC101 told me this past fall--and I quote--"People listening to KC101 just want to hear about music and shoes."
I was barefoot at the time.

My three-year contract was coming to an end on Dec. 31, and while I am not opposed to a radio show that emulates your Access Hollywood s and Entertainment Tonight s, with some music and one-liners thrown in for good measure, I had ideas of my own. They included me having final say in what happened on the show. Management was not prepared to concede that. I could stay on, continue in the direction the show was going, or I could choose not to renew. I went with the latter.

She may be right, though; more music, more Hollywood, faster, slicker, safer --that probably is the way to go on a Top 40 radio station.

What do I know? After all, I was just a guy in a Camaro looking for work.

Vinnie Penn's last day on the air was Dec. 10, 2004. He is presently in talks with Sirius Satellite Radio and has written a screenplay for Howard Stern Productions. A short story of his is included in the Contemporary Press collection Danger City, due out this spring. Tell him you love him and miss him at vinniepenn.net.