Pressly starred as "Violet" in the 1997 film Poison Ivy: The New Seduction. In 1998 she played a recurring role as the assassin Mika in the TV action series Mortal Kombat: Conquest. In 1999, Pressly was cast as the promiscuous dancer "Audrey" on the television series Jack and Jill. Pressly starred in the independent film Poor White Trash, playing scheming gold-digger Sandy Lake. She subsequently appeared in a number of films, including Not Another Teen Movie (playing Priscilla, a stereotypical high school cheerleader) and Torque, as a crazed, motorcycle-riding criminal. Pressly posed nude for the March 1998 and February 2004 issues of Playboy.

In 2001, she was made the new spokesmodel for Liz Claiborne Cosmetics and its fragrance Lucky You. She has performed with the band The Pussycat Dolls. In 2002, she was ranked #8 in Stuff magazine's "102 Sexiest Women in the World". In 2003, she launched a lingerie line, J'Aime, which later became a full sleepwear and ready-to-wear line.