Bringing Up Baby
"Bringing Up Baby" (1938)
Boy meets girl. Girl stalks boy in order to get him to look after her leopard. Girl falls in love with boy who's about to get married. Girl's dog steals dinosaur bone. Leopard runs away. Boy and girl sent to prison. Boy ends up in a dress. Boy falls in love with girl right back. Not exactly a Garry Marshall movie, but so much the better. Howard Hawks' 1938 film neatly followed the template set up by "It Happened One Night" in setting up a boy and a girl -- in this case soon-to-be-wed paleontologist David (Cary Grant) and prototypical Manic Pixie Dream Girl heiress Susan (Katharine Hepburn) -- to bicker and flirt across a series of adventures before falling in love at the end. But the formula was never quite as perfect as it was here, in part because Hawks retained what's so often absent in romantic comedies today. Simply, "Bringing Up Baby" is one of the funniest films ever made, riding the outstanding chemistry between Grant and Hepburn, each arguably giving the performance of their careers, through a series of uproarious set pieces. But as funny as the film is, Grant and Hepburn's courtship feels genuinely hard won, and you don't question the way that Grant's defenses gradually come down. It's also unusually subversive, especially for the era -- Grant is increasingly feminized, even to the point of ending up in a dress, while Hepburn was always one of the more masculine starlets, and it's her that's doing the pursuing. Maybe it's not a film that makes you swoon in the way of some of these other choices, but you'll be too busy battling a chortle-induced hernia to notice. -- Oliver Lyttelton

Annie Hall
"Annie Hall" (1977)
The moment in "Annie Hall" when Alvy Singer (Woody Allen) tries to recreate the lobster cooking moment that he originally shared with Annie (Diane Keaton) but with a different girl says a lot about the romantic comedy genre itself. Often limited by its conventions, there are times when the romantic comedy genre still seems fresh and inspired and other times, let's say most of the time, the formula seems dull and flat. When it was released in 1977, "Annie Hall" was a game-changer for the genre, and one of the few to win a Best Picture Oscar. The film also signaled a sea change for Allen, who would begin to transition out of his "early, funny" films and into more serious territory. The reason why the film endures, outside of being hilarious, is its refreshing honesty. While most romantic comedies are focused on showing two people discovering their true love through a series of outrageous misunderstandings, "Annie Hall" watched two people fall in and out of love with one another in a story that didn't feel completely predestined. Sure, Allen's Singer starts the movie wondering where things went wrong with Annie, but, in any other romantic comedy, the two leads would find a way to make it work in the end. "Annie Hall" isn't about pat endings. It's a comedy about the pursuit of love, and bumps along the way of finding a perfect match. Its honesty about the ups and downs of relationships is something few filmmakers have matched since. -- Ryan Gowland

Broadcast News
"Broadcast News" (1987)
Much like James L. Brooks did with his comedy-drama “Terms of Endearment,” which saw what could have been a maudlin cancer drama turn into a charming slice of Americana comedy, in 1987’s “Broadcast News” he took a romantic comedy formula we’ve seen in so many films and turned it on its head. The film stars the always affable Holly Hunter as the highly-touted news producer Jane, who’s caught in the middle of the affections of her dear friend Aaron (Albert Brooks) and the handsome news anchorman Tom (William Hurt), and the story film follows Jane’s quest to be seen as sexually attractive in the eyes of Tom. She ignores Aaron’s frequent advances, allowing Brooks to bring sympathy and relatability to a role that’s essentially Duckie from “Pretty In Pink.” In a role that was originally intended for Brooks’ 'Terms' lead Debra Winger, Hunter parts from the typically shrill depiction of the hardworking woman that’s been employed in films since, allowing audiences to relinquish in her quest for Aaron’s attention while also sympathizing with her shaky relationship with Aaron. It’s no surprise all three leads walked away with nominations for their performances, along with Brooks for his writing and Best Picture, as well as Martin Scorsese’s regular cinematographer Michael Ballhaus – who lends “Broadcast News” a cinematic look that certainly breaks away from the sitcom-level look of most romantic comedies today. Up until the film’s sweet climax, which lends a grounded realism to the love triangle that sends sparks flying throughout the film’s running time, “Broadcast News” acts as a romantic comedy that surely provides all the laughs, heart, and drama that you find in most Hollywood romcoms these days. -- Benjamin Wright