After college, Kenny performed stand-up comedy around the country for about eight years before he moved on to other venues. Kenny went to Bishop Grimes Junior/Senior High School, a Catholic high school. Describing Kenny's stand-up routines, Goldthwait said, 'Tom would get up there and talk about his therapist and he didn't even have a therapist, he just loved Woody Allen.'
He and Goldthwait went to the event, and performed under the monikers Tomcat and Bobcat, respectively, as a tribute to Crimmins, after which Goldthwait used Bobcat as his stage name. In their mid-teens, they saw an ad for an open-mic night at Skaneateles that featured comedian Barry Crimmins with the moniker 'Bear Cat'. He met Bobcat Goldthwait in first grade and they became lifelong friends. As a young child, he loved drawing and collecting record albums in the late 1960s and 1970s.
Kenny was born and raised in Syracuse, New York, to Theresa Bridget (Donigan) and Paul Austin Kenny.
