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Headey played Kitty Brydon, the childhood friend and romantic interest of Mowgli, in Disney's The Jungle Book (1994).James Berardinelli praised the cast's "solid performances" She appeared opposite Vanessa Redgrave in the 1997 romantic drama Mrs Dalloway, portraying the closest friend of a housewife, who is now wife of a self-made millionnaire and mother of five.
Despite a positive critical response, the film flopped at the box office, seeing greater success following its home release; it has since been recognised as a cult film.
In 2002, she appeared as a mousey Victorian lesbian artist with Gwyneth Paltrow and Aaron Eckhart in the mystery drama Possession, based on the 1990 novel of the same name by British author A. Byatt, and as the wife of a law-abiding art framer dying of leukemia in the thriller Ripley's Game, adapted from the 1974 novel of the same name.
In its review for the latter, Eye for Film noted: "Whilst this is very much a male-centered film, Lena Headey turns in a powerful performance as Jonathan's wife, creating a sense of balance and normality against which other events are contrasted".
In 2001's comedy The Parole Officer, Headey took on the role of a police officer, alongside Steve Coogan in his first film role.
While the film was warmly received, View London remarked: "The only disappointment is Lena Headey, who, despite being fantastically sexy (she's given both a nude scene and a 'dressed as a prostitute' scene), smirks her way through the entire film, even at the most inappropriate moments".