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Zellweger subsequently relocated to Los Angeles, a move she had postponed several times because she believed she lacked the talent and experience to be a competitive actor in that city.She would next appear in the coming-of-age drama Empire Records (1995).Marc Savlov of Austin Chronicle applauded the main cast saying they were "all excellent in their roles" and noted that "Zellweger's character – all squeals and caged sexuality – seems a bit too close to Juliette Lewis' Mallory Knox (of Natural Born Killers) to be as fresh as it should be".The part earned her an Independent Spirit Award for Best Debut Performance.Zellweger won the Academy Award for Best Supporting Actress for her performance as a loquacious farmer in the American Civil War drama Cold Mountain (2003). Braddock in Cinderella Man (2005) and author Beatrix Potter in Miss Potter (2006).

She also portrayed Roxie Hart in the 2002 musical film Chicago, directed by Rob Marshall and co-starring Catherine Zeta-Jones, Richard Gere, Queen Latifah, and John C. The movie garnered wide critical acclaim and won the Best Picture award at the 75th Academy Awards.

Roger Ebert, showing approval of Zellweger and Cruise's chemistry in it, wrote: "The film is often a delight, especially when Cruise and Zellweger are together on the screen.

He plays Maguire with the earnestness of a man who wants to find greatness and happiness in an occupation where only success really counts.

She earned her second Academy Award and BAFTA Award nominations for Best Leading Actress, winning her second Golden Globe Award for Best Actress – Motion Picture Musical or Comedy and the Screen Actors Guild Award for Outstanding Performance by a Female Actor in a Leading Role.

In 2003, following the success of Chicago, Zellweger starred with Ewan Mc Gregor in the little-seen and appeared in Anthony Minghella's war drama Cold Mountain, opposite Nicole Kidman and Jude Law, playing a woman who helps a farmer following her father's presumed death.

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She also served as an executive producer as she wanted to get more involved in the production.