Romantic comedies are considered guilty pleasures, not works of art. For that, they often get bad raps in the film business, not to mention the cheesy dialogues and a glaring lack of realism that make them nearly unwatchable.
Still, there are a few films that remind us why we enjoy movies—and romantic comedies in the first place. They have naiveté and vulnerability and a form of sincerity that makes them a great escape from reality.
Here are a few romantic comedy films that you should watch for a chill night in.
The Princess Bride, 1987
Beautifully quotable, The Princess Bride is an adaptation of William Goldman’s classic novel that was turned into a charismatic and relatable film, a lot due to its pop culture references that allow viewers to find themselves in the story.
The film is told from an outside party, so the tone shifts to tell a compelling tale, allowing the viewer to place themselves in the shoes of either character so you can see the magic through their eyes. This film creates an inviting world that defies expectations.
Say Anything, 1989
This rather iconic film showed John Cusack in his younger years, dealing with how youth can be aimless before they find their way. The characters are deeply genuine, and the film allows the audience to uncover their own lives for themselves as the voice of the MTV generation, trying to define who they are outside the labels placed upon them on their parents. This film catapulted John Cusack to stardom, which says a lot of the quality of the film.
When Harry Met Sally, 1989
Warm and hilarious at the same time, this film shows what it was like to be in love, years after their first encounters with each other. Billy Crystal and Meg Ryan had a natural chemistry that captures the essence of the story, with a witty and striking script that gave the film its iconic status as one of the best rom-coms to date.
Sleepless in Seattle, 1993
Sappy and predictable, Sleepless in Seattle is entertaining and sentimental, a nod to some of the most dazzling romances in Hollywood. Directed by Nora Ephron, the plot may be implausible, but because of the charm of the cast, the film, despite its corny nature, is enjoyable, especially as a date movie.
My Best Friend’s Wedding, 1997
The film is outrageously over-the-top and unrealistic, but you can’t help but love watching it anyway because the characters are charming and charismatic.
Julia Roberts’s character realized that she had been in love with her best friend, who happens to be engaged and getting married in a few weeks. So she tries to stop the wedding in an almost comical way, but the performances were so endearing that you would love watching them anyway.
Love Actually, 2003
Filled to the brim of celebrities from the United Kingdom, this film managed to make the story workable despite its numerous characters and subplots. Each of the stories have limited air time, so they were able to focus only on the essentials, making it consistently engaging because they didn’t need to stretch the stories too much.
It’s a sort of drugstore short story collection, but the way the stories were intertwined explores love with bonds of familial relationships. It’s not grounded in reality, but its charm still makes is shamelessly entertaining—a definite guilty pleasure.
Crazy, Stupid Love, 2011
Like Love Actually, this film is filled of interwoven stories done right—the American way. The ensemble cast is not overstuffed, and they were able to show not only love, but damage also brought about by the same four-letter-word. Because of the many views of love that the film showed, there is at least one of the characters that any member of the audience can relate to—and it’s hilarious, which is a plus.
What If, 2014
Can men and women ever be just friends? That is the question that the film wants to answer, and it is also what makes it relatable. However, they didn’t start platonic—Daniel Radcliffe and Zoe Kazan’s charming characters had sexual tension but managed to be friends despite of it, and that is what makes the film so adorable for its audience. It’s filled with clichés, yes, but they managed to do so in the most positive way possible.