The 76 Best Romantic Comedies of All Time

In Joan Micklin Silver’s Crossing Delancey, Amy Irving is Isabelle “Izzy” Grossman, a woman who has it all—dear friends, an interesting job, a rent-controlled Manhattan apartment—except, to her grandmother Ida’s chagrin, a husband. While Izzy lusts after Anton (Jeroen Krabbé), a worldly, married, author she meets at the bookstore where she works, Ida sets her up with a matchmaker, who in turn introduces Izzy to Sam (Peter Riegert), the owner of a nearby pickle shop. Though Izzy resists his unassuming charms at first, passing Sam off to a girlfriend, eventually, realizations and regrets give way to a happy reconciliation. 

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…to help you get your boss’s job:

Working Girl (1988)

First, consider the cast: Melanie Griffith, Harrison Ford—who owned the ’80s in Hollywood and made this his only rom-com—Sigourney Weaver, Joan Cusack, Oliver Platt, Alec Baldwin (at his douchiest), and Kevin Spacey. Next, look at the director: Mike Nichols—if there is a pantheon for romantic films, he probably has Zeus’s seat. Finally, the shoulder pads; my god, the shoulder pads. Were doorways made wider in the 1980s? Adventures in Babysitting aside, this movie is really as feminist as mainstream movies got in the ’80s. Melanie Griffith plays Tess McGill, a wily business school graduate working as a secretary at an investment bank with such memorable one-liners as “I have a head for business and a bod for sin.” When her boss (Weaver) steals her idea for a merger and then ends up out of commission (temporarily bedridden after a ski accident), Tess rises to the occasion: scheming with the support of her friends and maybe-lover (Ford), conniving, flirting, and using some good old-fashioned elbow grease to outwit her superiors, beat the boys, and claim the position she’s rightfully earned. Griffith is miraculous (one critic compared her to Marilyn Monroe; younger viewers might see a mold for Alicia Silverstone’s Cher), taking a role that could have just been “cute” and elevating it to nuanced and beguiling. That’s what this film is—so much so, we’ll forgive you if, after watching it, you suddenly have a soft spot for shoulder pads.