Chan got his start by enrolling in the TVB Dancers' Training Class in 1985. Soon after graduation, he joined a few of the studio's troupes that would accompany popular singers during their live performances. He worked with artists such as Alan Tam, Leslie Cheung, and Anita Mui before being invited by a producer to make a record of his own.
In 1994, he made his film debut with Twenty Something. Chan has since received several Hong Kong Film Award nominations: two for his role in He's a Woman, She's a Man (1994), and one each for Heaven Can't Wait (1995) and Big Bullet (1996). With 1996's Young and Dangerous, Chan established himself as a mainstay of the triad genre. The film was a huge success, and led to nine sequels and spinoffs before the series concluded in 2000. In 2005, Chan starred alongside Jay Chou as Kyoichi Sudo in Initial D.
Musically, Chan is known for bringing a hip hop flavour to cantopop. With his recent releases beginning around 2002, he has rapped and added hip hop beats to his music. His hip hop style has brought him new fans, although some Hong Kong fans have accused him of acting "black." He continues to incorporate R&B and hip hop sounds into his music today.