Brewster starred with Cameron Diaz and Christopher Ecclestone in the independent drama The Invisible Circus (2001), portraying a grieving teenage girl who travels to Europe in 1976 in search of answers to the suicide of her older sister.
Brewster had a four-episode arc between 2008 and 2009 on the NBC television series Chuck, as Jill Roberts, the title character's ex-girlfriend from Stanford.