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She also appeared in 1998's Hurlyburly with Sean Penn.
Ryan's first film of the 2000s was Hanging Up, a Diane Keaton-directed family comedy-drama about a trio of sisters who bond over the approaching death of their curmudgeonly father.
The same year, Ryan returned to type, starring alongside Tim Robbins in Fred Schepisi's romantic comedy I. The film centers on a mechanic and a Princeton doctoral candidate who fall in love, with the aid of the graduate student's uncle, Albert Einstein (played by Walter Matthau).
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".
Hanks and Ryan would be paired for a third time in the film You've Got Mail.
During college, she acted in television commercials and the soap opera As the World Turns to earn extra money.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.