Career:Pressly starred as "Violet" in the 1997 film Poison Ivy: The New Seduction. In 1998 she starred as "Nikki" on the short-lived TV series "Push", and also played a recurring role as the assassin Mika in the TV action series Mortal Kombat: Conquest. From 1999 to 2001, Pressly starred as "Audrey" on the drama 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 high school cheerleader) and Torque, as a crazed, motorcycle-riding criminal.
In 2001, she was made the new spokesmodel for Liz Claiborne Cosmetics and its fragrance Lucky You. 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. In 2006, Maxim magazine named her #34 on its annual list; she is also featured in its gallery. Pressly posed nude for the March 1998 and February 2004 issues of Playboy. She also appeared nude in the May 2006 issue of Allure. 
Pressly guest starred in episodes of several TV shows. In an episode of the WB series Charmed, played Mylie, a mermaid trying to find love; (Alyssa Milano who played Phoebe later guest starred on My Name is Earl.) Other series in which Pressly guest starred were The Twilight Zone, Fastlane, Becker. Night Man and Silk Stalkings. She also appeared in an episode of the prank series Punk'd.In 2005, Pressly was cast in the NBC sitcom My Name Is Earl, as Joy Turner. In 2007 she won the Emmy Award for Outstanding Supporting Actress in a Comedy Series for her work on the show. She has also been nominated for several other awards.
Pressly sang "Fever" in an appearance with the band The Pussycat Dolls. She has also appeared in a number of music videos, including "Girls of Summer" by Aerosmith and the Marilyn Manson cover of "Tainted Love". On May 31, 2006, she hosted the first annual VH1 Rock Honors.
Pressly was a producer as well as a star in the 2005 movie Death to the Supermodels. She hosted the October 7, 2006 episode of Saturday Night Live. Prior to this, she guest starred on an episode of MADtv from season eleven, where she played Hillary Clinton in a parody of My Name Is Earl, "My Name Is Dubya", in which George W. Bush (Frank Caliendo) makes a list of all the bad things he's done in the past and rectifies them one by one. She is featured in the 2008 video game Saints Row 2 in which she plays lead role Jessica, a lieutenant for the fictitious Brotherhood gang.