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). In 2015, she made her directorial debut with Ithaca, a film in which she also acted.