She is known for playing the best friend role in a string of successful romantic comedies such as You've Got Mail (1998), Miss Congeniality (2000), Two Weeks Notice (2002), and Bewitched (2005).

(2011) and she held a series regular role opposite Zach Galifianakis in the HBO series Bored to Death[1] and played Trish in the Amazon webseries Sneaky Pete (2017).

[2] In 2020, she appeared as a guest star in the Netflix series The Politician, for which she received praise for her performance.

[3][4] In 2024 she acted in the off Broadway revival of the Kenneth Lonergan play Hold On to Me Darling opposite Adam Driver.

[5] Christopher Barnard of Vogue praised her performance describing her as having "sharklike cunning and steadiness".