5. Sleepless in Seattle (1993)
Meg Ryan and Nora Ephron has already proven their rom-com chops four years previously in When Harry Met Sally…, but throwing Tom Hanks into the mix turned out to be a masterstroke.
Hanks’ widower moves to Seattle with his son, who calls into a radio show trying to set his old man up with a new wife, and Ryan’s engaged reporter falls for his emotional story despite being engaged herself.
One letter later, and the stage is set for a rom-com that generated an incredible amount of pathos for the relationship between two leads who spent very little screentime together, but you’re always rooting for them nonetheless.