Brewster was born on March 10, 1969, in Concord, Massachusetts. Her mother, Hathaway Brewster (née Tew), worked as a government official, and her father, Galen Brewster, worked as a school administrator. She has a younger brother, Ivan.
Brewster grew up in Massachusetts and moved to New York City to attend Parsons School of Design. During her first year, she made her acting debut and eventually dropped out of design school to pursue her acting career. In the mid 1990s, Brewster moved to San Francisco and enrolled in acting classes. As of 2014 she resides in Los Angeles.
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