In real life, I'm willing to debate whether or not romance is truly dead. There's a case to be made on either side. Fortunately, it will always be alive and well at the movies. And with the rapid approach of the only holiday dedicated solely to romantic love, movies about falling and being in it are going to be in heavy rotation. Valentine's Day calls for a movie that will make you believe in happily ever after, grand gestures, and listening to the advice of your wise and wise-cracking best friend. There are plenty of films that fit those criteria, but so few that include V-Day as part of the plot. For that — and for so many other things — I turn every year to departed romantic comedy queen Nora Ephron. Her Sleepless In Seattle is the one Valentine's Day movie that doesn't get enough love.
Released in 1993, Sleepless In Seattle is a part of the golden age of rom-coms. From the grown-up relationship drama of Moonstruck and When Harry Met Sally to the coming-of-age crushing in Pretty In Pink and Clueless, the '80s and '90s were the salad days of the genre. Sleepless stands out from its rose-tinted contemporaries for a couple of reasons. First of all, it cemented Tom Hanks and Meg Ryan as one of cinema's most charismatic pairings. And second, it's the only romantic comedy I can think of where the two leads don't really meet one another until the movie is almost over. And your screenplay has to be practically flawless to make that structure work.
Ephron's script for Sleepless really is that good. It tells the story of Annie Reed (Ryan), a woman who thinks she's found all the magic that's missing in her perfectly serviceable world when she hears a widower (Hanks) wax poetic about his deceased wife on a call-in radio show. Despite her dorky fiancé and reservations about the strangeness of it, Annie uses her journalistic resources to find out if Sam Baldwin is too good to be true. It's Sam's son's most fervent wish to see his dad happy again, and he has a promising feeling about one letter in the pile of fan mail that Sam's conversation with Dr. Marcia elicited: Annie's.
Both Annie and the movie are inspired by the 1957 Cary Grant and Deborah Kerr romance, An Affair To Remember. In that movie, the lovers first meet when they're not free, but make a plan to reunite in six months at the top of the Empire State Building so they can pursue a relationship. Annie borrows that idea, proposing in her letter that if Sam is interested in getting to know her, they meet at that very same spot — on Valentine's Day. Sam is understandably resistant to the idea of rendezvousing with strangers, but fate — in cahoots with a headstrong child — eventually gets her way.
Sleepless is just sweet enough, and never saccharine. It hits several melancholy notes on the way to its heartwarming resolution. It begins with two grieving men trying to figure out how they fit together without the glue that was Sam's wife and Jonah's mother. It's also often uproariously funny. Bees, secret Beatles messages, The Dirty Dozen, and tiramisu are all topics of witty and natural conversation. ("Some woman's gonna want me to do it to her I'm not gonna know what it is!") Jonah and Sam's relationship is offbeat and real. Rosie O'Donnell is a low-key MVP as Annie's pragmatic friend, Becky. And Hanks and Ryan are somehow able to play up their characters' chemistry while only sharing two scenes. Sam and Annie would be perfect together. You just know.
This Valentine's Day, treat yourself to a movie that's both blissfully romantic and achingly real. Sleepless In Seattle is a classic because it's among the most watchable and ageless romantic comedies ever made, catnip even to those who claim not to like the mushy stuff.