He became a teen idol for playing Dylan McKay on the TV series Beverly Hills, 90210 from 1990 to 1995, and again from 1998 to 2000. From 2001 to 2002, he starred in the HBO prison drama Oz, as the Reverend Jeremiah Cloutier. From 2002 to 2004, he starred in the post-apocalyptic television series Jeremiah. In 2006, Perry co-starred in the ensemble drama series Windfall. Perry appeared on Broadway in 2001, in a revival of The Rocky Horror Show, playing Brad Majors. In 2004, he appeared in the London production of When Harry Met Sally as Harry, alongside Alyson Hannigan as Sally. From 2017 until his death, Perry starred as Frederick "Fred" Andrews, Archie's father and owner of Andrews Construction, on the CW series Riverdale.