After moving to Hollywood in 1997, Reid transitioned to movies, landing her breakout role in 1998's "The Big Lebowski". Though the film disappointed at the box office, grossing only $17 million in the US, it has gone on to become a cult classic. Later that same year, she appeared in a larger role in a more financially successful film, "Urban Legend", where she portrayed a sexy radio host and which grossed just under $40 million in the US and led to two sequels, though neither included Reid. In 1999, she appeared in a tiny role in another hit, "Cruel Intentions". Reid found her first taste of real mainstream success when she portrayed the role of the virginal Vickie in "American Pie" (1999), which grossed over $100 million in the US. The film also marked her first film to reach number one at the box office. In 2001, she reprised the role in "American Pie 2", which opened to $45 million and grossed over $145 million in the US, almost 50% more than its predecessor. Reid did not return for "American Wedding" (2003), but did reprise the character in the fourth theatrical film in the series, "American Reunion" (2012).