The actress, who turns 58 years old today, made a name for herself when she starred opposite Billy Crystal in When Harry Met Sally. The film, which celebrated its 30th anniversary this year, also garnered Ryan her first Golden Globe nomination and became known as one of the greatest romantic comedies of all time.
The Connecticut native then went on to team up with Tom Hanks multiple times throughout the 1990s for films including Joe Versus the Volcano, Sleepless in Seattle and You've Got Mail. These two are truly a dream on-screen pairing!
In another of her most iconic roles, Ryan took on the part of a modern woman who meets a man, played by Hugh Jackman, from another era who she navigates a romance with in Kate & Leopold.
Take a look back at all of the performer's best rom com roles below.