When Harry Met Sally (1989)

When Harry Met Sally appears time and again on lists cataloging the best romantic comedies of all time, and it’s hard to disagree. Meg Ryan sky-rocketed to romantic comedy super-stardom as Sally, and, despite his atypical lack of Cary Grant-like charm or good looks, Billy Crystal somehow transformed into an adorably witty, romantic ideal. The story takes place over many years, and that’s part of what makes the romance believable. Punctuated throughout with real-life love stories told by the couples themselves, When Harry Met Sally is surely the template for the modern romantic comedy.

Benny & Joon (1993)

Before the days of his pirate-related celebrity, Johnny Depp appeared in this 1993 romantic comedy with Mary Stuart Masterson and Aidan Quinn. Depp plays an eccentric and quiet man named Sam whose dress and mannerisms perfectly mimic those of Buster Keaton. Sam falls in love with Joon (Masterson), a painter and artist suffering from schizophrenia who’s under the care of her older brother, Benny (Quinn). The odd premise provides ample opportunity for sweetness, hilarity and some of the most truly memorable and unique acts of love, including a lovely serenade performed by Sam with a squeaking balloon. It’s a simple story that showcases Depp in his character-acting prime.

Roman Holiday (1953)

Roman Holiday seems to be littered with the stuff love stories are made of: a princess in disguise, exotic locales and even a moonlit dance or two. To top it all off, it stars none other than Audrey Hepburn and Gregory Peck at the near height of their glamour. Unlike many films of the day, Roman Holiday is shot on-location in Rome, which means you won’t find any cheesy rear projection or matte paintings here. The city looks glorious, and Hepburn and Peck look glorious in it. Perhaps the most endearing part of Roman Holiday is that despite the seemingly cliché inherent plot, it veers away from the expected in the most surprising ways that will be sure to leave the audience spellbound.