No. 33: When Harry Met Sally
The kinder, gentler, funnier Jewish romance
1989, dir. Rob Reiner. We all know what this movie has going for it: Meg Ryan’s infamous fake-orgasm scene, over pickles and sandwiches at Katz’s deli. What it also represents is the moment when, anticipating Judd Apatow by 20 years, director Rob Reiner recast the contemporary Jewish man as a desirable romantic figure. Forget Woody Allen’s neurotic, passive-aggressive archetype; here instead is the kinder, gentler, funnier Billy Crystal, who can both be a friend and pull off a heart-stopping dip on the dance floor on New Year’s Eve, regardless of being shorter than his date in heels.