I get it. When you think of romantic comedies, you don’t think of traditional “masculine” fare. But these classic films are some of the great movies of all time and you’d be remiss if you missed them. Think of them as great comedy with a little more heart than you’re used to. 

When Harry Met Sally
When you think of “the classic” romantic comedy, you’re either thinking of You’ve Got Mail or you’re thinking of When Harry Met Sally. The latter of course being the much better film. This classic tale of two best friends explores the age old question of whether men and women can really be friends or if sex will always get in the way. It has all the standard tropes you’ve come to expect from a romantic comedy—but that’s more or less because this movie set them. The most memorable scene is one featuring Meg Ryan as Sally, faking a very loud orgasm in a public diner. When I say “most memorable” I mean it has its own section and two lengthy paragraphs on Wikipedia.

It Happened One Night
A wealthy and spoiled heiress runs away from her overbearing father in order to marry her supposed love, another money-seeking businessman. Her complete ineptitude in the real world quickly becomes apparent and she’s discovered by a roguish reporter who’s in desperate need of a scoop. He decides to help her get to her love in exchange for her exclusive story, but a little romance gets in the way. One of the very last comedies made before the MPAA code restricting content, the film is pleasantly racy and still incredibly modern in its wit and bite. The film was also the first movie ever to sweep the five major Academy Awards.

Four Weddings and A Funeral
Hugh Grant has a career thanks to the writing of Richard Curtis, and they first paired on what is arguably their best movie partnership, Four Weddings and A Funeral. The two of them would go on to collaborate on other classics such as Notting Hill, Bridget Jones Diary, and Love Actually, but it’s here that Grant really shines as the well-intended but socially awkward Charles, who falls in love with an American woman he keeps running into over the course of four weddings and a funeral. It’s heartwarming, heartbreaking, life-affirming, and generally fun. Many a best man could take instruction by studying Charles’ speech at the beginning of the film.

Moonstruck
The great thing about Moonstruck is that if you just read the script as it’s written, it would read like a classic drama. Instead, all the actor’s turn it up juuust a pinch and the result is a beloved comedy rife with romance. Cher—yes, Cher—won an Academy Award for her portrayal of a widowed Italian American woman who falls in love with her fiancé’s estranged (and strange) brother (Nicholas Cage) after trying to invite him to their wedding. With beautiful moments, classic lines, and a slew of BAFTA and Academy Awards, it’s no wonder this romantic comedy classic shows up on so many “Best Of” lists.

What’s Up Doc?
This is my all-time favorite comedy. The film stars Ryan O’Neal and Barbra Streisand in a madcap screwball comedy surrounding four identical luggage bags that get swapped around through a series of mishaps and misdeeds in a single hotel. Directed by Peter Bogdanovich, this adorable homage to the 1930s romantic screwball comedies has it all: a musicology conference, slapstick firemen, a CIA hunt, a cocktail party hijacking, a Chinese dragon heist, and one of the funniest car chase sequences ever captured on camera. 

Your Sister’s Sister
I first encountered Your Sister’s Sister at the Tribeca Film Festival on the whim of a friend who’d purchased our tickets and I quickly found myself enchanted. The simple story follows a man still dealing with the death of his brother who is sent by his female best friend to her family’s remote island cabin. Upon arrival, he meets his friend’s lesbian sister grieving a loss of her own, and after a night of heavy drinking they sleep together. The next morning they’re surprised by the arrival of the sister/friend and a host of shenanigans ensue. Shot over the course of 12 days with a mumblecore vibe, the film is a real down-to-earth delight you won’t want to miss.