Lee joined TCS on a contract in 1995 after emerging as 1st runner-up in the male category of the Star Search programme in 1995. He worked as a factory worker, salesman and part-time model before joining star search in 1995.

Lee first started acting in Chinese-language television dramas produced by Channel 8. Lee rose to prominence in his career after winning the Best Actor award at the Star Awards 1997 for his role as a hanjian in the television drama The Price of Peace, set in Japanese-occupied Singapore during World War II. In 1998, he starred as Yang Guo in The Return of the Condor Heroes, an adaptation of Louis Cha's novel of the same title.