A relative newcomer to the screen, the actress first garnered attention with a recurring role on the NBC soap "Days of Our Lives." Reid excelled in supporting roles that traded on her sexuality as in "Around the Fire" (1998), in which she played the hippie girlfriend of a privileged youth; "Girl" (also 1998), which cast her as a tough rock musician; and "Urban Legend" (also 1998), in which she portrayed Sasha, a college radio therapist. She continued in the same vein with turns in "Cruel Intentions" (1999), a modern spin on "Dangerous Liaisons" with teenage protagonists, and "American Pie" (also 1999), about high school students out to lose their virginity by graduation day.
In the wake of "Pie's" huge box office bonanza, Reid became a familiar face among up-and-coming young Hollywood. She distinguished herself even more with her high-profile relationship with her brief fiance, MTV host Carson Daly; her wild party girl behavior; and her skin-baring outfits than she did for her body of work. Reid's stellar roles at the then heady, post "American Pie" fame of the late 1990s included the alleged victim of a he-said, she-said sexual encounter in the dreadful "Body Shots" (1999); one of Richard Gere's daughters and the females besetting him in director Robert Altman's "Dr. T and the Women" (2000); and the living embodiment of the Archie Comics dumb blonde in the pop-rock misfire, "Josie & the Pussycats" (2001). Reid managed to squeeze in a return to the role of Vicky Latham for "American Pie 2" (2001), though her part had been drastically cut, as well as a turn in the campus comedy – and "Animal House" wannabe – "National Lampoon's Van Wilder" (2002).
In 2003, her film "My Boss' Daughter," an uneven comedy that sat on the shelf for two years, was released when star Ashton Kutcher's star suddenly rose. Reid played the tempting offspring of Kutcher's employer. Reid turned in some of her funniest work as Danni, J.D.'s (Zach Braff) obsessive girlfriend, in a recurring role on the NBC sitcom "Scrubs" beginning in 2003. But again – no sooner would she prove her onscreen chops – than her work would be eclipsed by her off-screen reputation. Particularly notorious was a 2004 red carpet incident in which the seemingy oblivious actress accidentally bared her breast for the paparazzi, revealing its apparent surgerical enhancements.
She next appeared in the howlingly bad thriller "Alone in the Dark" (2005) before developing a TV comedy pilot riffing on her hard-partying reputation. After little network interest, Reid signed on as the new host of E!'s venerable travel series, "Wild On..." – rechristened "Taradise" in her honor – beginning in the fall of 2005. But as past experiences dictated, the locational E! show proved too much temptation for the late night party girl. The show's ratings tanked, and, despite Reid's pleas to be taken seriously as an actress, the series did nothing for her career and only reaffirmed her wild child image.