After graduating in the mid-nineties Gary worked for the C.P.A. firm then called Coopers & Lybrand. He also decided this was the opportune time to pursue his child hood dream of “telling jokes on tv.” He would work a 12-hour day as an accountant and then spend his nights on a quest for performance time at every comedy venue in New England. For years he would often drive six hours or more in exchange for most times nothing more than five minutes with a stage and a microphone. Gary would perform in rock clubs, used book stores, bars, dance clubs and anywhere else that would indulge his fervor for comedy.
After two years Gary left his accounting job and subsequently worked as a substitute high school teacher and Starbucks Coffee employee in order to allow himself more time to devote to his growing passion for writing and performing jokes. Also he was bored of being an accountant He spent those years on a relentless mission to become a professional stand-up.
In 1999, after thousands of open-mike shows and countless hours writing and rewriting jokes in what became piles of composition notebooks, Gary was selected to perform in the prestigious Montreal International Comedy Festival. Within six months of his performances at this showcase, attended by hundreds of comedy industry elites he reached milestones that many entertainers never reach. That fall, he performed on The Tonight Show with Jay Leno, The Late Show with David Letterman, and secured a deal to write and star in a biographical situation comedy for Twentieth Century Fox.