While starring on 90210, Perry then won a supporting role in the original film version of the Joss Whedon's Buffy The Vampire Slayer (1992). In an attempt to find more mature roles, he decided to leave Beverly Hills, 90210 in 1995.

Perry had already become a very popular teen idol in the early 1990s. In the same year, he took a part in the Italian movie Vacanze di Natale '95, playing himself.

He stated: "When you're in the professional acting business, you have to look into all these offers and I don't mean anything bad about it but creatively it's something I have done before and I don't know how it will benefit me if I do it again." Perry finally revealed a major reason as to why he did not want to be part of this revival, citing the show's long-time producer Aaron Spelling: "The difference between CW bringing something back and Aaron Spelling doing something back is significant.

In 2007, he landed the role of Tommy "Santa" Santorelli on the film The Sandlot: Heading Home and in the 2008 western A Gunfighter's Pledge.

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

Following this, he then won the role of brooding millionaire's son Dylan Mc Kay on Fox's teen drama, Beverly Hills, 90210.

He had auditioned for the role of Steve Sanders, a role that went to actor Ian Ziering, before being cast as Dylan.

In this dramatized audio, Perry played the characters of Saint Stephen and Judas the disciple.

The project also featured a large ensemble of other well known Hollywood actors including Jim Caviezel, Lou Gossett Jr., John Rhys-Davies, Jon Voight, Gary Sinise, Jason Alexander, Christopher Mc Donald, Marissa Tomei and John Schneider.

His other voice work includes The Incredible Hulk, Biker Mice from Mars, Mortal Kombat: Defenders of the Realm, and The Night of the Headless Horseman.

Aside from his role on Family Guy, Perry has also guest-starred as gay characters in the sitcoms Spin City (1997) and Will & 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 Mc Farland on Will & Grace.

Perry moved to Los Angeles shortly after high school to pursue acting as he did not have any opportunities to do so in Ohio.