While Lee was in high school his grandmother worried about his choice of acting as a career. He recounts that when she asked "What are you going to fall back on?", he responded, "'Well, grandma, if I have something to fall back on, won't I fall back?', which is sort of a youthful attitude, but I've always followed my gut". Lee moved to New York at the age of 18 to try to become an actor. He graduated from the American Musical and Dramatic Academy in Manhattan (two-year program). In 1986 - 89 he worked at the Empire Diner in New York. "I wasn't a great waiter. I was funny, but I gave a lot of attitude," he said in Rosie Magazine, March 2002. However, he said, "The place is like a vortex for me." Two marriages and a career came out of there, he explained. Both Tanya Lewis and Leslie Howitt worked there. And, in 1989, the diner was where he met Tom Fontana (Writer and Director of Oz), who lived around the corner from the diner. Lee did some stage work during this time. "I was doing plays all the time, but there's no money in it," Lee said in a 1995 Los Angeles Times article, "After graduation, I thought I'd be making a living at it". His big brother, Chris Tergesen, kept him on track, "If you love it, you have to stick with it" he told Lee.