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She plays a woman who believes in this guy she loves, and reminds us that true love is about idealism." Zellweger also starred in the 1998 drama One True Thing, opposite William Hurt and Meryl Streep, as a woman forced to put her life on hold in order to care for her mother who is dying of cancer.
One True Thing took in a modest US million in the US, Variety magazine's Todd Mc Carthy stated about Zellweger: "Projecting gravity and impatience that she hasn't shown before, Zellweger is outstanding as the smart young woman who resents the interruption to her life's momentum but ends up growing in ways she never would have expected." In 2001, Zellweger gained the prized lead role of Bridget Jones, opposite Hugh Grant and Colin Firth, in the British romantic comedy Bridget Jones's Diary, based on the 1996 novel of the same name by Helen Fielding.
Zellweger accomplishes the small miracle of making Bridget both entirely endearing and utterly real."Zellweger took on the role of a former actress serving as a foster mother, alongside Michelle Pfeiffer, in the drama White Oleander, for which she received a Satellite Award nomination for Best Supporting Actress – Drama.
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.
For Nurse Betty (2000), she won her first Golden Globe, and for her portrayals of Bridget Jones in Bridget Jones's Diary (2001) and Roxie Hart in Chicago (2002), she garnered two consecutive Academy Award nominations for Best Actress.
She reprised her role as Bridget Jones in two equally successful sequels (2004–2016).
The film earned critical acclaim but grossed a modest US million at the North American box office.
She also served as an executive producer as she wanted to get more involved in the production.
With George Clooney in his directorial venture, the period comedy Leatherheads (2008), about the early years of professional American football, Zellweger portrayed a Chicago Tribune newspaper reporter. criticized her role, remarking that she, "as the kind of lippy heroine epitomized by Rosalind Russell, is miscast in a role that demands snark, not sleepy-eyed sweetness".
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.