The actor went on to more television work, guest starring on the short-lived high school set series "The Faculty" (ABC) and "Social Studies" (UPN) in 1997, and taking a recurring stint on The WB's highly rated family drama "7th Heaven". He returned to the big screen in 1998 with featured parts in the rodeo-set "The Ride" and the high-school graduation night comedy "Can't Hardly Wait", portraying a stealthy kleptomaniac who relieves the hosting home of dozens of items in a mostly silent performance. He followed up with a role in the 1999 teen comedy "She's All That", playing a bully whose torturous tactics against diminutive Simon (Kieran Culkin) are foisted back upon him by the valiant Zack (Freddie Prinze Jr) in a memorably vile scene. Not long after, the actor was impressive in a much different part, as the social outcast math whiz best friend of aspiring astronaut Homer Hickman in the acclaimed biopic "October Sky". Owen was featured later that year as 'The Sherminator', an unlikely Casanova out to impress his friends in the successful teen sex romp "American Pie"--he also reprised the role for the 2001 sequel.
Off the success of the "Pie" films, Owen was soon cast in a string of youth-oriented and/or rauch-minded comedies, including Brian Robbins' wrestling comedy "Ready to Rumble" (2000)--opposite Ahmet Zappa and David Arquette as a dedicated fan of professional wrestling-- and the college comedies "Going Greek" (2001), "Van Wilder" (2001), "A Midsummer Night's Rave" (2002) and "National Lampoon Presents Dorm Daze" (2003). Continuing his association with the Lampoon brand, Owen co-starred with Will Friedle in "National Lampoon's Gold Diggers" (2004) as a pair of clueless con artists who hope to make a fortune by marrying a pair of Beverly Hills matrons.