In 1995, Bowen took her first series regular role, co-starring on the short-lived ABC adventure series "Extreme" as the sweet but sassy love interest of a member of a Rocky Mountain rescue unit. 1996 guest roles on Fox's "Party of Five" and "Strange Luck" followed the early demise of "Extreme", and that same year she was featured in the box office comedy hit "Happy Gilmore", playing the sharp, strong-willed woman who sparks the romantic interest in the titular unorthodox golfer (Adam Sandler). Her additional feature credits included the less successful comedy "Multiplicity" (1996) and 1997's "An American Werewolf in Paris", in which the actress rose to the challenge of performing in full monster makeup.
Bowen returned to series television in 1998, playing grifter and martial artist Amanda Webb, one of "Three" former career criminals drafted into a covert government operation. This adventure series on The WB offered Bowen, usually typecast as the girl-next-door, the chance to play a femme fatale action hero, and she brought to the role a nice balance of over-the-top posturing and down-to-earth frankness. She reached a much larger audience on NBC's "ER" with a 1998-99 part as yet another love interest, this time the brittle insurance saleswoman girlfriend of Noah Wyle's Dr. Carter.
Turns in the UPN TV-movie "The Last Man on Planet Earth" (1999) and a 2000 episode of "Dawson's Creek" were of the less memorable sort, but Bowen quickly recovered with a regular role on "Ed" (NBC, 2000-2004). A charming comedy-drama produced by David Letterman's Worldwide Pants, "Ed" was a somewhat sardonic but sincerely heartfelt show and a perfect fit for Bowen's talents. Here she played Carol Vessey, a teacher and former high school golden girl who captured the imagination of the title character in high school, and captured his heart upon his return to their sleepy hometown. Quick with a quip and particularly skilled in scenes that addressed her character's romantic uncertainty, Bowen helped to give Carol Vessey the kind of multifaceted portrayal that was needed to make her an engaging character. This role would help to further Bowen's familiarity to TV viewers.
While her work in television has been both prolific and successful, Bowen has continued to pursue film roles and was featured in the romantic comedy "Venus and Mars" (2001) and the Tim Allen vehicle "Joe Somebody" (2001). After the final episode of "Ed," Bowen remained a regular presence on television--and ABC in particular--in 2005, with recurring roles on the short-lived John Stamos series "Jake In Progress" and the hit drama "Lost"--on the latter she played the injured bride of the physician Jack (Matthew Fox). The following fall, she was added as a regular to the retooled second season of "Boston Legal" as attorney Denise Bauer. She appeared back on the big screen in "Kids in America" (2005) as a close-minded, dictatorial high school principal whose increasingly repressing censorship policies inspie her students to rebel.