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Released to mixed reviews by critics, Ryan's first film release of 2008 was The Deal, a satirical comedy film based on Peter Lefcourt's 1991 novel of the same title about Hollywood.Directed by Steven Schachter and co-starring William H.In Luis Mandoki's When a Man Loves a Woman (1994), a romantic social drama film also starring Andy Garcia, she played an alcoholic high-school guidance counselor.The film and her performance were both well received by critics.Dutton's directorial debut Against the Ropes (2004), a fictionalized sport drama about American boxing manager Jackie Kallen, the first woman to become a success in the sport. Following a three-year hiatus, Ryan returned to film with Jon Kasdan's 2007 independent film In the Land of Women, a film she described as "kind of like The Graduate, but with cancer".Starring alongside Kristen Stewart and Olympia Dukakis, she played Sarah Hardwicke, a mother and wife facing breast cancer, who connects with her neighbor's much younger grandson, played by Adam Brody.
Also in 1994, Ryan won Harvard's Hasty Pudding Woman of the Year award, and People Magazine dubbed her one of "the 50 most beautiful people in the world." In 1995, critic Richard Corliss called her "the current soul of romantic comedy." That same year, she appeared opposite Kevin Kline in Lawrence Kasdan's French Kiss, a romantic comedy that catered to her "America's Sweetheart" image, and Ryan was awarded the Women in Film Crystal Award.
Hanks and Ryan would be paired for a third time in the film You've Got Mail.
In 1994, Ryan took a role that differed from the romantic-comedy ingenue character for which she had become famous.
In 1986, she played Carole Bradshaw, the wife of Naval Flight Officer Nick "Goose" Bradshaw (played by Anthony Edwards) in Top Gun. (1989), which paired her with comedic leading man Billy Crystal and earned her a Golden Globe nomination.
Ryan appeared in the film Innerspace (1987) with her future husband Dennis Quaid, and later in the remake of D. Her portrayal of Sally Albright includes an oft-recounted scene in which her character, lunching with Crystal in Katz's Delicatessen in Manhattan, theatrically demonstrates for him how easy it is for a woman to fake an orgasm.