Her Campus Logo Her Campus Logo
The opinions expressed in this article are the writer’s own and do not reflect the views of Her Campus.
This article is written by a student writer from the Her Campus at Mt Holyoke chapter.

While they’re perhaps unrealistic, sappy, and oftentimes downright corny, slipping into the idealized world of a romantic comedy is always an effective pick-me-up at the end of a hard week, allowing us to imagine realities where the guy always gets the girl and everyone finds their happy ending. While I’m aware that “classic” is subjective and everyone will probably have their own definition, for the purposes of this article, my definition is the films that have been canonized in the genre as the rom-coms to watch. For me, classic rom-coms are all those that came out roughly between the 80s and the early 2000s, establishing and inventing some of the core tropes of the genre that continue to define the modern rom-com aesthetic. So, grab your popcorn, tissues, significant other you’ll force to watch the movie with, or whatever accompaniment you find necessary, as below are listed my personal favorite classic rom-coms!

  1. The Princess Diaries (2001)

Apart from being one of my favorite rom-coms, The Princess Diaries is just one of my favorite movies in general, filled with so many iconic scenes and quotes: “Me? A princess? Shut up!” case and point. I grew up watching this movie, so it feels very near and dear to my heart. And, let’s be real, who hasn’t identified with Mia Thermopolis at one point in their life? This is a movie for all the girls who ever felt outcasted or “invisible” in high school, so it’s nice, even if only for one hour and fifty-five minutes, to see ourselves as the title character: an awkward, unpopular teen who discovers she is actually the princess and heir of a fictional country, turning her whole world upside down. I know everybody loves Chris Pine in The Princess Diaries 2, but not only do I love the first movie more for how it centers Mia and Queen Clarisse’s relationship, but I honestly like Michael more than Nicholas — I mean, the “you saw me when I was invisible” line, are you kidding? Their love story is simple and subtle, but still incredibly endearing, and I will always shake my fist at the producers for writing him out of the story in the sequel.

  1. When Harry Met Sally (1989)

I acknowledge that, on a technical level, When Harry Met Sally is probably a better movie than The Princess Diaries (even if The Princess Diaries is my favorite), so it was only *just* edged out of the top spot. Are you more of an enemies to lovers or friends to lovers person? With Harry Met Sally, you don’t have to choose, because this movie does them both perfectly. Starting off on the wrong foot when they meet during their college years, main characters Harry and Sally keep running in and out of each other’s lives, finally establishing a friendship in their post-college years that blooms into what is, in my opinion, a love story embodying the pinnacle of the rom-com genre. This movie has the added bonus of being the perfect watch for any season. Fall, Christmas, New Year’s? It covers every season of the couple’s budding relationship in the backdrop of New York City in the 90s. As far as I’m concerned, Harry’s monologue at the New Year’s Eve party is essential viewing for anyone who calls themselves a rom-com fan, and I will die on the hill that it is the rom-com of all rom-coms. 

  1. Ella Enchanted (2004)

Soooo I definitely have a nostalgia bias here as well, but I do also truly believe that this movie is so good! It’s set in a wonderfully wacky fantasy world and borrows from a number of different fairy tales in telling the story of Ella, a girl who was given the gift of obedience by her fairy godmother when she was born, blessed—or more appropriately, cursed—to do whatever anyone tells her. On her journey to find her fairy godmother and break the spell, she meets Prince Char—a take on the eponymous Prince Charming archetype—and glorious romance ensues . . . plus a 70s rock power ballad performance or two. Anne Hathaway is as charming as ever, the modern references are so funny and clever, and the “Somebody to Love” scene was a cultural reset. What more could you want?

  1. Clueless (1995)

Not including Clueless in at least the top 5? As if! One thing about me, I am obsessed with Jane Austen, so of course the fact that Clueless is a loose adaptation of Emma means it comes out pretty high on the list. With peak Paul Rudd dreaminess, so many iconic quotes, and a great cast of characters, Clueless is just so fun to watch and rewatch and will surely make you pine for the nostalgic 90s days of “rolling with the homies.” Following the hijinks of the ditzy and fashion-forward teen protagonist as she endeavors to makeover and matchmake her new friend, Ty, Cher Horowitz delights in meddling in other people’s love lives . . . until she becomes entangled in her own schemes. This movie is endlessly quotable and hilarious from start to finish, and no, we are NOT going to talk about the ex-step-sibling thing!

  1. While You Were Sleeping (1995)

With Sandra Bullock in the lead as the infinitely endearing Lucy, this movie walked so Dear Evan Hansen could run, not going to lie. Lucy is a lonely token collector for the Chicago Transit Authority who lives alone with her cat, so already she is such a mood. After she saves her crush, Peter—an attractive man who frequents her booth every morning—when he falls onto the train tracks, resulting in him entering a coma (honestly, the synopsis is crazy now that I am actually writing it out), a miscommunication in the hospital results in his family thinking Lucy is engaged to him. If you love the drama of miscommunications, this movie will be an absolute blast for you, as, in typical rom-com fashion, things get complicated as Lucy gets to know Peter’s family and begins falling in love with Peter’s brother, Jack, instead. More than just a romance, it’s a movie about loneliness not just in a romantic sense, but also familial, as Peter represents not just the ideal man to Lucy, but the perfect family she herself does not have. It will be sure to tug at your heartstrings as much as it’ll leave you giggling and kicking your feet.

  1. Pretty in Pink (1986)

While I still maintain Andie should have ended up with Duckie instead of Blaine (ugh), Pretty in Pink is one of my favorite 80s movies, filled with great music, fittingly absurd outfits, and the classic trope of the star-crossed rich boy and the girl from the “wrong side of the tracks.” Duckie’s “Try a Little Tenderness” dance is one of my favorite scenes in any movie ever, and yes, he is my favorite part of this movie . . . But Molly Ringwald is of course so charming as well (Andie would definitely be a Mount Holyoke Student), embodying that age-old and romantic—if unrealistic—teenage fantasy harbored by all the “not-like-other-girls” of falling in love with the most popular guy in school. It’s candy-coated, it’s cheesy, it’s so 80s, and it’s amazing. 

  1. 10 Things I Hate About You (1999)

If you can’t tell already, I love a good literary retelling in rom-com form. 10 Things I Hate About You adapts Shakespeare’s The Taming of the Shrew with all the 90s angst and grunge you could possibly want. Following the blueprint of the Shakespeare story, Joseph Gordon-Levitt’s Cameron is new to town and falls in love with Bianca Stratford, only to learn she is not allowed to date until her older sister, Kat, does. Cameron then hires and pays Heath Ledger’s character, Patrick, to date Kat, and while it all starts as a ruse, he ends up falling for her for real. This movie is so great because the love interests are quite antithetical to a typical rom-com — Kat is a Bell Jar-reading, hotheaded feminist who marches to the beat of her own drum (even if it means being generally regarded as a “frigid b*tch” by her classmates). Patrick is a similarly rebellious figure, regarded as a “bad boy” delinquent by the other characters in the movie. I love the way Kat always keeps Patrick on his toes, and their strong personalities balance each other out so well in a romance that will keep you guessing until the very end! 

  1. Bridget Jones’ Diary (2001)

Bridget Jones is probably the most relatable rom-com protagonist in this list, and her love story is very . . . unconventional to say the least, filled with no shortage of secondhand embarrassment-inducing moments involving bunny costumes, fireman’s poles, and cheetah print underwear that make for one gut-busting ride. Perhaps more than the others on this list, this movie really captures the realities—all the mishaps, miscommunications, and more often than not, mortifications—of navigating one’s love life. This movie is yet another modern retelling of a Jane Austen novel, this time of Pride and Prejudice, so that boosts it in my good books for sure. And having Colin Firth and Hugh Grant both vie for your heart? That’s the dream, honestly. I highly recommend this movie!

  1. Notting Hill (1999)

This movie is truly one for the fanfic girlies—the fanfic blueprint, one might even say—as it stars Hugh Grant as Y/N. Well, actually, his name is Daniel Thacker, a travel bookshop owner who lives his Harry Styles-esque fantasy when he falls in love with superstar actress Anna Scott, played by Julia Roberts, after a chance encounter. Perhaps second to Harry’s monologue from Harry Met Sally is Roberts’ iconic line “I’m just a girl, standing in front of a boy, asking him to love her” that just guts me every time, followed by one of my favorite rom-com chase scenes ever. This is essential rom-com viewing for sure, also great to plug into if you’ve just finished watching Hugh Grant in Wonka and need a palette cleanser!

  1. You’ve Got Mail (1998)

You’ve Got Mail further solidifies that Nora Ephron truly is that girl in the rom-com world, helming yet another classic in the genre. The romance in this movie is so juicy, as main characters Cathleen and Joe fall in love over an online correspondence, unaware that they know each other in real life and, more than that, despise each other. The combination of the perky, optimistic children’s bookstore owner vs. the cold, cynical business mogul of a competing book superstore is such a fun instance of the grumpy x sunshine trope to watch play out. While it is unconventional in that the two love interests don’t really interact much in-person until the end, it’s a testament to the strength of the writing and the performances that it’s still such a great romance, portraying the much more adult realities of love than some of the fluffier teen films in this list. 

  1. 13 Going on 30 (2004)

I love that this movie is literally just Big but for the girls, and yes, while the concept is slightly creepy given that Jenna is in the mindset of a 13-year-old girl as she engages in adult relationships, the concept overall is fun enough to make us all wish to be “30, flirty, and thriving.” I am such a sucker for the childhood friends-to-lovers trope, and let’s be real, who wouldn’t fall for Mark Ruffalo as Matt? This movie offers a really valuable lesson and cautionary tale about how a single choice can change the entire trajectory of your life, as young Jenna sacrifices her friendship with Matt for popularity and then sees these consequences play out when she wishes to be a grown-up, finding herself having to repair their damaged relationship. The “Thriller” dance scene is so iconic, and the whole movie exudes such gushy early 2000s nostalgia that you can’t help but love it. 

Sarah Grinnell

Mt Holyoke '26

Hi! My name is Sarah, and I am a sophomore at Mount Holyoke with a prospective double major in English and studio art. I love to read (Jane Austen is one of my faves <3), write, paint, and watch movies and cartoons, and I'm super geeky for all things fantasy and sci-fi