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. At the time of being cast, she was in college and considering alternate career options. 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'. 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 1998, she enrolled at Barnard College in New York City, but dropped out to continue pursuing acting. Shaw completed roles in various independent films for the remainder of the 1990s. She played a considerably larger 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.

She then landed parts in a handful of television roles. 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 also signed on with the Elite Models agency in 1989 at the age of 13 before beginning her acting career, and did a few modeling jobs and commercial work throughout her earlier career. Shaw made her first formal performance in a UCLA acting camp short at age 10, and subsequently toured with children's folk singer Peter Alsop at age 11. Her name, Vinessa, spelled with an 'i' rather than the common 'a', was a variation of her grandfather's name, Vincent. Her family's original surname was ' Schwartz', and her ancestry includes Jewish (from her paternal grandfather), Italian (from her maternal grandfather), German, Irish, English, Mexican, and Swedish. Shaw's father, a native of Los Angeles, is a psychologist and former adjunct professor of psychology at Antioch University.

Vinessa Elizabeth Shaw was born on July 19, 1976, in Los Angeles, California, the daughter of Larry Shaw and actress Susan Damante.

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