In 2000, Sheen jumped to the small screen when he replaced Michael J. Fox for the last two seasons of the sitcom Spin City. For his work on Spin City, Sheen was nominated for two ALMA Awards and won his first Golden Globe for Best Performance by an Actor In A Television Series – Musical Or Comedy. The series ended in 2002.
In 2003, Sheen was cast as Charlie Harper in the CBS sitcom Two and a Half Men, which followed the popular Monday night time slot of Everybody Loves Raymond. Sheen's role on Two and a Half Men was loosely based on Sheen's bad boy image. The role garnered him an ALMA Award and he gained three Emmy Award nominations and two Golden Globe award nominations