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Shaw had made her film debut in a little-known-of 1981 slasher film called Home Sweet Home, which dealt with a serial killer targeting a family at Thanksgiving time. She then landed parts in a handful of television roles. She played a considerably large role in Disney's 1993 Halloween family film Hocus Pocus alongside Bette Midler, Sarah Jessica Parker, Kathy Najimy, Omri Katz, and a young Thora Birch. Shaw completed roles in various independent films for the remainder of the 1990s.
In 1998, she enrolled at Barnard College in New York City, but dropped out to continue pursuing acting. Shaw was attending the college when she was approached by Stanley Kubrick for her role in Eyes Wide Shut, playing a prostitute who is encountered by Tom Cruise's character. In a 2008 interview, Shaw stated that Kubrick was "very influential" to her and that he "was the first person who encouraged her to continue acting". At the time of being cast, she was in college and considering alternate career options. Following her role in Eyes Wide Shut, Shaw played parts in a handful of films including the independent 2000 mystery-drama The Weight of Water with Sarah Polley and Sean Penn; the slapstick comedy Corky Romano alongside Chris Kattan; the romantic comedy 40 Days and 40 Nights, playing the feisty ex-girlfriend of Josh Hartnett's character; and a very small role in Woody Allen's Melinda and Melinda.
More low budget and independent films consumed Shaw's time until 2006, where she returned to the big screen in Alexandre Aja's remake of Wes Craven's exploitation-horror film The Hills Have Eyes, playing a young mother on a camping trip with her family who is attacked by bloodthirsty mutants in the New Mexico desert. Director Aja had wanted to cast her in the film after seeing her performance in Eyes Wide Shut. Asked why she wanted to act in a horror film, Shaw responded "Well, I guess I could be good in it since I'm so frightened of those kinds of concepts. But this one in particular really attracted me because of the filmmakers. I really thought that they had a great stance on it. Like it's very different, very heartfelt, and heartbreaking because of the characters involved. So that's kind of what made the difference. It was more of an actor's piece, if you can believe that, in a horror movie.” Shaw was featured on the official one sheet promotion poster for the film, which was a box-office success.
Shaw was in the 2007 remake of the classic Western film 3:10 to Yuma with Russell Crowe and Christian Bale, the indie drama film Garden Party, as well having a leading role in Two Lovers alongside Joaquin Phoenix and Gwyneth Paltrow. That film premiered at the Cannes Film Festival in 2008 and was released theatrically in February 2009.
In 2013, she had a supporting role opposite Jude Law's character, playing his wife in Side Effects.