I found this video of Jennifer Ringley’s appearance on the Letterman show hidden away on an unlabeled VHS tape that had been sitting in a drawer probably since the day I recorded it.

Better her than me! 🙂

In 1998 I was contacted by the talent people at Letterman. They wanted me on the show to talk about (what else?) payphones. I later inferred that they were casting about trying to find something unique to this still-rising Internet thing, and they had a choice between me and Jenni, and most likely others as well.

If faced with a choice between a depressed dude looking for human contact through ringing payphones and a young woman getting naked on the Internet I think their choice to go with Jenni was a no-brainer.

That said, there was a legitimate Letterman connection, in that my website was partly inspired by his skits where he called payphones in NYC and talked to whoever answered. Those could be awesomely funny.

But in retrospect I am confident Dave would have made me look like an idiot, deliberately or not.

His interview w/Jenni had some prescient questions and observations, I thought, even if they were probably funneled to him directly from his more web-savvy staff.

I’ve been a fan of lifecasting, too, though like everything Internet it’s become relatively commonplace. I had multiple still-image webcams for many years, as early as 1995, I believe; and I also streamed live on CuSeeMe once in a while. It seemed like all I ever found on CuSeeMe was men masturbating.

Now I livestream the view from my apartment window 24/7. I maintain surveillance cameras in all my rooms but little of that gets shared publicly.