Carey co-starred in the series, The Good Life where he met Bruce Helford, with whom he began a successful, collaborative writing relationship.

Carey wrote and starred in his own Showtime special, Drew Carey: Human Cartoon, for which he won a CableACE award. He was also nominated for a CableACE award in 1993 for his performance at the Tenth Anniversary of the Montreal Comedy Festival.

Carey returned to his stand-up comedy roots in July 1997, when he hosted HBO's Mr. Vegas All-Night Party. He also hosted the 1997 CableACE Awards and the 1998 American Music Awards.