Play It Again, Sam (1972)

Play It Again, Sam is special because it turns romantic misery into a buoyant, brainy kind of comedy—one where the jokes come from self-awareness as much as circumstance. Woody Allen’s neurotic film-critic persona is both hilariously specific and strangely universal, and the movie’s Casablanca obsession becomes a clever lens for all the bad advice we give ourselves when we’re lonely and trying to look cool. The tone is light, quick, and charmingly theatrical, with dialogue that snaps and characters who feel like real friends even when they’re behaving like fools. If you don’t enjoy Allen’s anxious, talky style it may not be your tempo, but if you do, this is a perceptive, witty crowd-pleaser that still feels fresh in the way it laughs at love without ever quite giving up on it.

Play It Again, Sam is clearly aiming for a sweet, self-aware romantic comedy about post-divorce panic, using Casablanca as a crutch and Bogart as the fantasy “coach” in your head. When it works, it’s charmingly neurotic and delivers some genuinely funny, movie-buff riffs with a likable, low-stakes warmth. But if you’re expecting the sharper bite or wilder unpredictability of peak Woody Allen, you may find the story pretty conventional, with a few flat, perfunctory stretches and an arc you can see coming from miles away. And if tidy, too-perfect endings make you roll your eyes, this one leans into Hollywood symmetry over deeper messiness, which might leave you smiling but not really feeling much.