July 24, 2021

20 of the Best Romantic Comedies of All Time

8 min read

The best medicine for dark times is a romantic comedy. If you disagree, you clearly never had a totally rotten day instantly cured by some Nora Ephron magic. When you watch a movie that includes a soundtrack with both Louis Armstrong and The Cranberries, you’ve got a recipe for happiness. These movies are engineered to be mood-boosters and often feature memorable classic lines; someone who was, at one time, referred to as “America’s Sweetheart”; and a comically memorable best friend. It’s these qualities on which we can rely. Here, all the rom-coms you can watch right now to brighten your quarantine mood.


10 Things I Hate About You (1999)

This is a 1990s Seattle-grunge take on Shakespeare’s The Taming of the Shrew. Julia Stiles stars as Kat Stratford, who is considered abrasive and unapproachable by her classmates. Her younger sister, Bianca (Larisa Oleynik), is a bubbly preppy type who just wants to be allowed to date, but their father (Larry Miller) won’t allow that until Kat does. New-kid Cameron (Joseph Gordon-Levitt) hires the school bad boy Patrick Verona (Heath Ledger) to take Kat out so Cameron can land Bianca as his girlfriend. This plot is full of so many twisty elements, it’s like…Shakespeare or something.

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Clueless (1995)

Cher (Alicia Silverstone) is the most popular girl in her high school. When she meets new student Tai (Brittany Murphy) and Tai suddenly becomes more popular than her, Cher gets a new perspective on life—while also falling for her stepbrother Josh (Paul Rudd).

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You’ve Got Mail (1998)

This is the movie that established that fall in New York, particularly on the Upper West Side, is magic; that all dogs named Brinkley are automatically charming; and that “Patricia makes coffee nervous.” Get a bouquet of freshly sharpened pencils and settle in for take two of Meg Ryan/Tom Hanks 1990s chemistry.

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His Girl Friday (1940)

Everyone deserves a rom-com, even journalists. When New York newspaper editor Walter Burns (Cary Grant) discovers his ex-wife, reporter Hildy Johnson (Rosalind Russell), is getting married to a boring insurance agent, he tries to deter her from settling down by enticing her with a big murder story. But soon Hildy becomes entrenched in the story and in finding the truth. A woman and a leadership role in the newsroom: a match made in heaven.

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Four Weddings and a Funeral (1994)

Charles (Hugh Grant) hasn’t been very lucky in love. He spends a lot of his time attending various weddings with his ragtag group of friends, and it’s there he meets Carrie (Andie MacDowell). Suddenly they’re crossing paths at other nuptials (and one funeral). Charles holds tight to the idea that he and Carrie are meant to be, even if their timing is never quite right.

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The Apartment (1960)

This is a different kind of Upper West Side romance. Insurance man C.C. Baxter (Jack Lemmon) will get a promotion if he lets his manager use his apartment to be with his mistress (Shirley MacLaine), who, it turns out, is Baxter’s crush from work. So, is it gonna be love or career success?

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While You Were Sleeping (1995)

Lucy (Sandra Bullock) is a transit worker who fantasizes about Peter, a customer she sees every day (Peter Gallagher). When Peter falls and hits his head on the train tracks, Lucy saves his life. While Peter is in a coma, Lucy gets to know his family and lets them believe she’s his fiancée. But Lucy’s also starting to fall in love with Jack (Bill Pullman)—Peter’s brother.

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Sleepless in Seattle (1993)

Sam’s (Tom Hanks) wife has just died, and he moves with his young son Jonah (Ross Malinger) to Seattle. On Christmas Eve, Jonah calls a radio therapist to help his dad get a new wife. Soon, Sam’s got letters coming in from all over the U.S., including one from a Baltimore reporter named Annie (Meg Ryan). “You don’t want to be in love. You want to be in love in a movie,” Annie’s friend Becky (Rosie O’Donnell) tells her. And that right there, folks, is the whole premise of this wonderful film.

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Something’s Gotta Give (2003)

Harry Sanborn (Jack Nicholson) is an old womanizer used to his habits. While away with his girlfriend, Marin (Amanda Peet), at her mother’s Hamptons beach house, he has a heart attack and ends up moving in to recover. Of course. Marin’s mother, playwright Erica Barry (Diane Keaton), is tasked with taking care of the ornery Harry, and she ends up getting way more than she bargained for. And then we get the best crying scene in romantic-comedy history.

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Imagine Me & You (2006)

Let’s hear it for a queer rom-com! This London-set movie, about out lesbian florist Luce (Lena Headey) and closeted married woman Rachel (Piper Perabo), is not often recognized in the rom-com genre, but it’s got everything a good one should: a charming child, a woman who owns a charming business, British accents, and a happy ending that doesn’t involve a heaping dose of heteronormativity! Also, Cersei’s just a simple Londoner with a crush on a pretty girl. Don’t we love that for her?

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How to Lose a Guy in 10 Days (2003)

Andie Anderson (Kate Hudson) works for a women’s magazine but wants to report hard-hitting stories. When she pitches the idea of getting a man to leave her after 10 days, her boss (Bebe Neuwirth) jumps at it. Ben Berry (Matthew McConaughey) is on a separate mission to get a woman to fall in love with him in 10 days. Obviously, this makes for great comedy.

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When Harry Met Sally (1989)

If you watch movies for their dialogue, this one will satisfy. Harry (Billy Crystal) and Sally (Meg Ryan) first meet while driving from Chicago to New York together after college graduation in the late ’70s. Over the years, they keep running into each other and eventually become friends, but Sally never forgets what Harry once told her on that drive: “Men and women can’t be friends.” This movie explores that theory and also allows Carrie Fisher to drop the classic line, “I will never want that wagon-wheel coffee table.” And once you learn that Sunday isn’t included in Sally’s “days of the week underwear” “because of God,” you won’t think of anything else.

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Moonstruck (1987)

Italian-American widow Loretta Castorini (Cher) is a bookkeeper living in Brooklyn Heights with her family. Before her boyfriend Johnny (Danny Aiello) leaves for Sicily to be with his dying mother, he proposes and Loretta accepts. Johnny asks Loretta to invite his estranged brother Ronny (Nicolas Cage) to the wedding, but once she meets Ronny, Loretta realizes she agreed to marry the wrong brother. You know, that classic problem. Also, this one got Cher and Oscar, so it deserves your attention.

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My Best Friend’s Wedding (1997)

Julianne and her best friend, Michael (Dermot Mulroney), had a pact that they’d marry each other by the time they turned 28. Four days before Julianne’s birthday, Michael announces he’s going to marry 20-year-old Kimberly (Cameron Diaz). Julianne travels to Chicago to try and stop the wedding, because, it turns out, she’s in love with Michael.

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Pretty Woman (1990)

Garry Marshall has a way of crafting romantic comedy that instantly becomes canon. Pretty Woman is a modern take on Cinderella; Vivian Ward (Julia Roberts) is a sex worker hired by the wealthy Edward (Richard Gere) to play the role of his girlfriend for six days. Yeah, if we start analyzing this one under a feminist lens, we’ll never stop. Anyway, this turns into a love story, and Vivian does get some killer lines along the way. “Big mistake—huge!”

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Bend It Like Beckham (2003)

Jess Bhamra (Parminder Nagra) is a teen living in West London whose strict Indian parents disapprove of her love for soccer. But when Jules (Keira Knightley) recruits Jess to her team, Jess’s talent shines and she falls for the coach, Joe (Jonathan Rhys Meyers). Jess wants nothing more than to become a professional soccer player—all she needs is her parents’ approval. One might also say this movie is begging to be a queer rom-com and misses the mark, but that’s just one woman’s opinion.

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Love Actually (2003)

It seems every actor in England is in Love Actually, which is probably the main reason people watch it even when it’s not the holiday season. The movie revolves around ten separate stories that are all delightfully interwoven and which all somehow feature excellent turtlenecks. Hugh Grant, Colin Firth, Emma Thompson, Alan Rickman, and more will positively charm you.

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Bridget Jones’s Diary (2001)

Bridget Jones (Renée Zellweger) is 32, single, and obsessed with her boss, Daniel Cleaver (Hugh Grant), at the publishing company where she works. She decides it’s time to start recording her life in a diary, and at her parents’ New Year’s Eve party, she reconnects with Mark Darcy (Colin Firth), whom she knew from childhood. Instead, Bridget dates Daniel, who is not exactly committed to monogamy, and learns to move on, get a new job, and excels. But no matter how much her life changes, Mr. Darcy always seems to be part of her story.

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13 Going on 30 (2004)

It’s Jenna’s (Jennifer Garner) 13th birthday, and she’s fed up with middle school. She wants to be “30, flirty, and thriving.” She ends up getting her wish when she wakes up as a 30-year-old magazine editor living in Manhattan. The only problem is she’s not the kind of person her childhood best friend, Matt (Mark Ruffalo), wants to be around anymore. Jenna has to come to terms with the choices she made, make changes to her life, and try to be the person 13-year-old Jenna would be proud of.

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