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.
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).
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.
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.