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Her other films include The Doors (1991), When a Man Loves a Woman (1994), Courage Under Fire (1996), Addicted to Love (1997), City of Angels (1998), Proof of Life (2000), and The Women (2008). She has two sisters, Dana and Annie, and a brother, musician Andrew Hyra, a member of the band Billy Pilgrim.
In 2015, she made her directorial debut with Ithaca, a film in which she also acted. Her parents divorced in 1976 when she was 15 years old.
Subsequently, she began to appear in supporting roles in films during the mid-1980s, achieving recognition in independent movies such as Promised Land (1988) before her performance in the Rob Reiner-directed romantic comedy When Harry Met Sally...You've Got Mail once again paired Ryan with Hanks, earning her a third Golden Globe nomination and making over 0 million worldwide.She also appeared in 1998's Hurlyburly with Sean Penn.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." 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.
(This award is given to "outstanding women who, through their endurance and the excellence of their work, have helped to expand the role of women within the entertainment industry.") In 1997, Ryan voiced the lead role in the animated film Anastasia, which garnered good reviews and enjoyed box office success.