Glass was born and raised in the suburbs of Philadelphia, Pennsylvania. He first began performing stand-up comedy in Philadelphia in 1982 while attending Conestoga High School. He made his earliest television appearances in the late 80s on A&E's An Evening at the Improv and in the early 1990s on several Comedy Central stand-up programs.
Glass is perhaps best known for his appearances as a contestant on the second and third seasons of NBC's Last Comic Standing and has appeared regularly on programs such as Jimmy Kimmel Live!, Late Night with Conan O'Brien, Tough Crowd with Colin Quinn, The Dennis Miller Show, Politically Incorrect, Louie, Tosh.0, Mr. Show with Bob and David, Preston and Steve and had his own Comedy Central Presents special in 2001.