After graduating from Wayland High School in Wayland, Massachusetts he went on to Skidmore College where he graduated with a BA in Psychology.

Debuting in the Eric Mittleman short film “The Pitch” as a pathetic kiss-ass employee, Gary went on to host The Helmetcam Show and Stripsearch, both on Playboy TV. His quick wit and sarcasm were the cornerstones on his on-camera persona as he interviewed and explored the multitude of adult stars and strippers that populated his programs. One of the more amusing aspects of his live performances were the frequent occasions when he'd talk "above the heads" of his often clueless guests.

As an offshoot of his Playboy work, he occasionally appeared on E! Entertainment Television’s Wild On series. Upon the cancellation of The Helmetcam Show he moved exclusively behind the camera, and went on to produce several other Playboy TV projects including Night Calls, Private Calls and The Weekend Flash.

Beginning as the co-author of “National Ninja Week” with Gregg Kavet (1981), he continued his comedy writing as the Humor Editor of The Skidmore News. Later he wrote for all the shows he hosted or produced on Playboy TV, additionally he sold the unproduced script “Naked at the White House,” as well as articles for Playboy documenting his various exploits in Las Vegas. He is currently writing a book about his experiences as Helmetcam Man working for Playboy TV.