When Harry Met Sally…

Reiner’s romantic comedy When Harry Met Sally… (1989), which paired Crystal and Meg Ryan as a set of platonic friends who fall in love, was credited with establishing the standard for the genre. He turned to darker material with Misery (1990), an adaptation of a King novel that…

…soundtrack for Rob Reiner’s film When Harry Met Sally…, which included performances by his jazz trio and his own rendering of such classic songs as “But Not for Me” and “I Could Write a Book.” The album went multiplatinum and earned Connick his first Grammy Award, for best jazz vocal…

…from the Train (1987) and When Harry Met Sally… (1989). Crystal earned his first film-writing credit for cowriting Memories of Me (1988), in which he also starred.

…wildly popular romantic comedy classics When Harry Met Sally… (1989) and Sleepless in Seattle (1993). She also directed the latter film, which starred Tom Hanks and Meg Ryan. After several critical and commercial failures, Ephron returned to Sleepless in Seattle’s winning formula in the late 1990s, once again pairing Hanks…

…and Her Sisters (1986), and When Harry Met Sally… (1989).