The best romantic comedies, from A to Z

Chemistry is perhaps the most elusive of all cinematic ingredients. Critics can point to craft in elements like directorial technique, set design, editing, and the rest; great acting can be taught, and recognized as such. But chemistry is out of everyone’s hands. Either people have it with one another or they don’t. Until you get two people together and watch the sparks fly, it’s a complete X factor. But to take that essential romantic ingredient and add comedy on top of it? It’s like trying to film someone performing a flawless tightrope walk while simultaneously walking a second tightrope yourself. Thus, The A.V. Club has compiled the following A-to-Z list of the most essential romantic comedies, to highlight the brilliance and difficulty of this remarkable cinematic balancing act.

It should be noted that the rules for what movies qualify as a rom-com are tough to articulate: At a certain point, Supreme Court Justice Potter Stewart’s rule about pornography comes into play: We can’t define “rom-com” precisely, but we know it when we see it. Hence, something like The Graduate fails the test, while Punch-Drunk Love’s fundamental humor and romance at its heart allow it to make the cut. Plus, there are certain lauded qualities of contemporary rom-coms (such as the “comfort food” consideration) that rank as less meritorious in the evaluation of great cinema. Still, the below films all demonstrate the requisite ingredients in spades—and anyone not seeing their own treasured rom-com nominees is encouraged to make the case for them in the comments. Fighting for the object of your affection? That’s amore.

This article was originally published on February 7, 2022.

A: The Apartment (1960)

“Shut up and deal.” Billy Wilder was perhaps the master of comedic last lines (see also: “Nobody’s perfect”), but Shirley MacLaine’s response to “Miss Kupelik, I absolutely adore you” belongs to the rom-com annals. In this fairly bleak 1960 workplace comedy (possibly the only film on this list with a suicide attempt), Wilder hero C.C. Baxter (Jack Lemmon) fights for the love of an elevator operator while battling her clueless married boyfriend (Fred MacMurray), who also happens to be his boss. As much a statement on the pointlessness of the rat race as on the saving grace of love, The Apartment itself transforms from a clandestine hookup pad to a cozy nest where tennis rackets are used as spaghetti colanders, lit candles signify the highest level of fine dining, and a game of gin rummy is the surest sign of romance. [Gwen Ihnat]Few films on this list have had as massive an impact on the modern romantic comedy as Annie Hall. Woody Allen’s mid-’70s masterpiece set the template for contemporary rom-coms with a staggering degree of new twists on old formulas. From the fourth-wall-breaking tactics of Allen’s nebbish protagonist to the master class in editing, the movie serves as the crowning jewel on his decade as America’s foremost cinematic humorist, and captures essential truths about urban romance at the same time. [Alex McCown]