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Several television films and smaller film roles followed, including appearances in Charles in Charge, Armed and Dangerous, Amityville 3-D and Promised Land; for her role in the lattermost she received her first Independent Spirit Award nomination. Her first leading role was the romantic comedy film When Harry Met Sally...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.

You've Got Mail once again paired Ryan with Hanks, earning her a third Golden Globe nomination and making over 0 million worldwide.

Ryan subsequently established herself, both nationally and internationally, as one of the most successful actresses in the 1990s and early 2000s, particularly in romantic comedy films such as Sleepless in Seattle (1993), French Kiss (1995), You've Got Mail (1998), and Kate & Leopold (2001).

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.

Also starring Keaton, Lisa Kudrow, and Walter Matthau, the film adaptation of Delia Ephron's 1995 novel received poor reviews from critics.

The same year, Ryan was cast in the action thriller Proof of Life with Russell Crowe, directed by Taylor Hackford.A year later, she once again returned to her romantic comedy roots with Kate & Leopold (2001), alongside Hugh Jackman.