While attending Barnard College, Shaw was cast in a supporting role in Stanley Kubrick's Eyes Wide Shut (1999), after which she decided to continue acting into her adulthood.

During this period, she also appeared in several feature films, including Steven Soderbergh's psychological thriller Side Effects (2013), and the crime drama Cold in July (2014).

[10] Though not a box-office success, Ladybugs gained an audience through regular subsequent television broadcast, and helped establish a fan following for Shaw.

[3] Shaw played a considerably larger role in the Disney Halloween-themed family film Hocus Pocus (1993) alongside Bette Midler, Sarah Jessica Parker, Kathy Najimy, Omri Katz, and Thora Birch.

[13] The same year, Shaw enrolled at Barnard College in New York City, but ultimately dropped out to continue pursuing an acting career.

[14] Shaw was attending the college when she was approached by Stanley Kubrick for her role in Eyes Wide Shut (1999), playing a prostitute who is encountered by Tom Cruise's character and who discovers she has HIV.

[15] Following her role in Eyes Wide Shut, Shaw played parts in a handful of films including Kathryn Bigelow's mystery-drama The Weight of Water (2000) with Sarah Polley and Sean Penn, in which Shaw portrayed a Norwegian immigrant who is the victim of an axe murder; the film and its source novel are both partly based on a real double-murder that occurred on Smuttynose Island in 1873.

"[21] Shaw had a supporting role as a barmaid in James Mangold's remake of the classic Western film 3:10 to Yuma (2007), co-starring Russell Crowe and Christian Bale.

[15] She next appeared in the Eddie Dodson biopic Electric Slide (2014), followed by the crime thriller Cold in July (also 2014), a film adaption of the 1989 novel of the same name, opposite Michael C. Hall, Sam Shepard, and Don Johnson.

[29] Shaw had a supporting role in the depression-era sports drama 12 Mighty Orphans (2021), based on American football coach Rusty Russell (portrayed by Luke Wilson).

[34] Shaw became a member of the Soka Gakkai International, a Nichiren Buddhist organization, during her first year attending college in 1996: "I was lonely and depressed, and I had so many questions about life.

"[14] As a core practice of Nichiren Buddhism, Shaw chants daimoku daily,[35] and is also a facilitator of the SGI-USA lay Buddhist Association for Peace, Culture, and Education.