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After appearing in the music video 'Be Chrool To Your Scuel' for the band Twisted Sister alongside Alice Cooper, Perry's earliest roles were in the daytime soap operas Loving (1987-88) and Another World (1988-89).

Following this, he then won the role of brooding millionaire's son Dylan McKay on Beverly Hills 90210. While starring on 90210, Perry then won a supporting role in the original film version of the Joss Whedon-written Buffy The Vampire Slayer (1992). Although the film was not a success, Perry had already become a popular teen idol in the early 1990s.

Perry starred as Lane Frost in 8 Seconds in 1994. In an attempt to find more mature roles, he decided to leave Beverly Hills 90210 in 1995. In the same year, he took a part in the Italian movie Vacanze di Natale '95, playing himself. Although he announced that 90210 was behind him, his departure would eventually turn out to be for only three years. During that time, Perry starred in the TV sci-fi movie Invasion (1997), a Rodney King-era drama Riot (1997) and also made a cameo appearance in Luc Besson's sci-fi adventure film The Fifth Element (1997).

Perry starred in the 1999 film Storm

He starred in a 2002 television movie called The Triangle.

From 2002 to 2004, he starred in the post-apocalyptic TV series Jeremiah.

In 2006, Perry co-starred in the ensemble drama series Windfall, about a group of friends who win the lottery. The series ran for 13 episodes during the summer of 2006 on NBC.

He starred in the 2007 film The Sandlot: Heading Home.

Perry appeared in the HBO series John from Cincinnati, which premiered on June 10, 2007, and ran for 10 episodes, with the series finale airing on August 12, 2007.

Perry is scheduled to star in a Swedish production with the title Midsommarfesten (The midsummer party). Most filming will take place in the small town of Trosa and the film is directed by Ian McCrudden. Filming will start in the fall 2008.

Perry has done considerable voice-over work for various animated series, often playing himself. He played himself (and Krusty the Clown's half brother) in an episode of The Simpsons (1993).

He voiced himself in an episode of Johnny Bravo, giving Johnny dating advice after Johnny saved him from a stampede of fan girls.

Perry voiced himself once again in an episode of Family Guy, where he was labeled as gay by Peter and sues the family. Peter tries to seduce Perry into revealing his homosexuality and fails horribly. However, by the end of the episode Perry is seen with Mayor Adam West, about to engage in sex.

Perry's other voice work includes The Incredible Hulk, Biker Mice from Mars, and Mortal Kombat: Defenders of the Realm. He also played Superman in the film Superman: Quest for Steve.

Aside from his self-parodying role on Family Guy, Perry has also guest-starred as gay characters in the sitcoms Spin City (1997) and Will and Grace (2005). He appeared as Carter Heywood's ex-boyfriend who subsequently fell in love with a woman on Spin City, and played a geeky birdwatcher who caught the eye of Jack McFarland on Will & Grace.

Perry was reunited with former 90210 co-star Jennie Garth when he guest starred in What I Like About You, where he played a character who claimed he had been dating Val's (Jennie Garth) best friend when he and Val became romantically involved (clearly a parody of the 90210 "Brenda years").

He guest-starred as Rev. Jeremiah Cloutier in the HBO television series Oz. He is featured in a full-frontal nudity scene in Oz.

He most recently guest-starred as rapist Noah Sibert, in the season premiere of the television series Law & Order: SVU (2008).

He also recently guest-starred as cult leader Benjamin Cyrus in an episode of Criminal Minds (2008).

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.

Perry was married to former model Rachel Minnie Sharp from 1993-2003, until they divorced. The couple share joint custody of their two children, Jack (born June 1997) and Sophie (born June 2001).