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Due to her success as an actress, she dropped out of college a semester before she planned to graduate.After her film debut in George Cukor's Rich and Famous, Ryan played Betsy Stewart in the daytime drama As the World Turns, from 1982 to 1984, and her character was featured in a popular romantic story arc.

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Subsequently, she began to appear in supporting roles in films during the mid 1980s like box office hit Top Gun, achieving recognition in independent films such as Promised Land (1988) before her performance in the Rob Reiner-directed romantic comedy When Harry Met Sally...She studied journalism as an undergraduate, first at the University of Connecticut and then at New York University.During college, she acted in television commercials and the soap opera As the World Turns to earn extra money.While the film became a lukewarm critical and commercial success, grossing million worldwide, it garnered much reportage in the tabloid press in association with Ryan and Crowe's affair.

A year later, she once again returned to her romantic comedy roots with Kate & Leopold (2001), alongside Hugh Jackman.

A film about a British Duke who travels through time from New York in 1876 to the present and falls in love with a successful market researcher in the modern New York, the James Mangold-directed film received a mixed-to-positive response, In 2003, Ryan broke away from her usual roles, starring alongside Mark Ruffalo and Jennifer Jason Leigh in Jane Campion's erotic thriller film In the Cut.