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Aniston's biggest box office success to date was her appearance in 2003's Bruce Almighty, in which she played the live-in girlfriend of Jim Carrey's title character.

Aniston then starred in the 2004 film Along Came Polly opposite Ben Stiller.

In late 2005, Aniston appeared in two major studio films, Derailed and Rumor Has It ….

In 2006, Aniston appeared in the low-budget drama Friends with Money, which was first shown at the Sundance Film Festival and received a limited release.

Aniston's next film, The Break-Up, which was released on June 2, grossed approximately $ 39. 17 million during its opening weekend, despite lukewarm reviews.

In 2006, Aniston directed a hospital emergency room-set short film called Room 10, starring Robin Wright Penn and Kris Kristofferson as part of Glamours Reel Moments film series.

Aniston noted that she was inspired to direct by actress Gwyneth Paltrow, who also directed a short film in 2006.