In 1995, Pauly Shore spotted Bobby Lee on stage and asked the young comedian to open for him in Las Vegas. It was at that point that Lee met Shore's mother, the celebrated owner of the Comedy Store, Mitzi Shore. Lee became a regular at the club, and also went on the road with the Hispanic comic Carlos Mencia.

Lee has appeared in over 20 national commercials, and has performed stand-up on Late Friday, Premium Blend and The Tonight Show. In summer 2004, he appeared in the big screen comedy Harold & Kumar Go to White Castle.

During the 2005 U.S. Open, Lee was in a commercial for IBM's Helpdesk.