She got her first substantial film roles in 1998, appearing in the Ed Wood-scripted I Woke Up Early the Day I Died, The Big Lebowski, the independent film Around the Fire, and Urban Legend, the latest in a long line of teen slasher flicks. Reid won some amount of recognition for the last film, which featured a Who's-Who line-up of post-pubescent stars and cast her as a campus radio talk show host. The following year, Reid earned a form of screen immortality with her role as the girlfriend of one of four high school guys who make a pact to lose their virginity in American Pie. She also appeared in more low-profile roles in the independent film Girl and in Cruel Intentions, which featured her as one of Ryan Phillippe's more unfortunate conquests. Later that year, she had a starring role in Body Shots, playing one of a group of twenty-something friends on the prowl for love and/or sex in Los Angeles.