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30 Best Romantic Comedies Every Woman Needs in Her Life
1. When Harry Met Sally
Nora Ephron wrote a perfect screenplay — this is not up for debate — that at its heart asks, "Can men and women ever really be friends?" In the case of Harry and Sally, the answer is yes, they can be. Friends and soulmates.
Eva (Julia Louis-Dreyfus) starts dating Albert (James Gandolfini), and when she realizes one of her massage clients (Catherine Keener) is Albert's ex-wife, she doesn't tell either of them about the connection. Instead, she fishes around for information and hilarity (and heartbreak) ensues.
"Show me the money." "You had me at hello." "Did you know the human head weighs 8 pounds?" It's no coincidence everyone you know can quote at least one (and probably all three) of these Jerry Maguire lines. The Tom Cruise/Renee Zellweger/Cuba Gooding, Jr. vehicle — about a sports agent who gets a conscience — is the kind of movie that worms its way into your brain and stay there for years to come.
This is more of a sports-rom than a rom-com, but it's a love story for the ages regardless. The movie follows Monica and Quincy as they go from ball-playing kids to ball-playing teens to ball-playing lovers to ball-playing exes to "Play me." "For what?" "Your heart." Epic.
There are so many Drew Barrymore movies to choose from! In this one, she plays a copy-editor who goes back to high-school undercover for a big-break story — and falls in love with a teacher in the process. The movie makes the list for many reasons: the wardrobe, the Shakespeare references, the existence of Molly Shonnon. Above all, it makes the list for bringing a character called Josie Grossy into our lives.
If you think about the plot for too long — sex worker falls in love with arrogant rich man — it can start to feel icky. So don't do that! Just enjoy it for what it is: an iconic movie that showcases the uncanny charm of one Julia Roberts.
Julia Roberts and Dermot Mulroney play best friends who made a pact to marry each other if they didn't find the love by 28 (lol, yes, 28). With her birthday fast approaching, he announces an unexpected engagement — and she realizes she's in love with him and must sabotage the wedding. Spoiler-ish alert: It doesn't end they way you think it would.
Cameron Diaz plays the title character, a woman who has an incredible effect on the men in her life — all of whom are (pretty inappropriately) competing with each other for her attention. It's brought to you by the Farrelly Brothers, the guys who did Dumb & Dumber, which is why you'll recall some truly batshit scenes, like the one where Mary puts
9. Sleepless in Seattle
Another Nora Ephron classic (co-written and directed by her). The story follows a widower named Sam (Tom Hanks) who calls into a radio show to discuss his heartbreak and attracts the attention of countless female listeners. Among them is a woman named Annie (Meg Ryan), who’s engaged to be married but feels like something is missing in her relationship. With a little scheming by Sam’s son, Sam and Annie eventually meet at the top of the Empire State Building.
We've all been Bridget Jones at one point in our life: single, fretting over men, and utterly disgusted by the thought of working out. Renee Zellweger brings the character to life perfectly, and Hugh Grant and Colin Firth as her love interest are not too shabby themselves.
The premise of this movie doesn’t sound comedic — young woman has an abortion after a one-night stand leaves her pregnant — but writer-director Gillian Robespierre’s hilarious script brings a lot of light to a plot that could easily end up feeling dark. It helps that Jenny Slate is perfect as Donna, a hapless comedian/bookstore clerk who has some very relatable thoughts on what women’s underwear looks like at the end of the day.
Richard Linklater’s iconic tale of Jesse and Celine isn’t *technically* a comedy, but it certainly delivers in the romance department. After meeting on a train in Europe, Jesse and Celine spend all night walking and talking in Vienna. They part ways at the end of the movie, but fear not — their story continues in the sequels Before Sunrise and Before Midnight.
There have been countless movie adaptations of Shakespeare over the years, but this 1999 classic remains the platonic ideal of Shakespeare adaptations. This one has everything — a fantastic cast (Julia Stiles, Heath Ledger, Gabrielle Union, Joseph Gordon-Levitt), an amazingly ’90s soundtrack (Letters to Cleo, Save Ferris, the Cardigans), and what must be the only successful attempt in cinematic history to make paintball look romantic.
Like Obvious Child, Knocked Up tells the story of a woman who finds herself pregnant after a one-night stand, only in this one, she decides to keep the baby. At first Alison (Katherine Heigl) and Ben (Seth Rogen) don’t seem to work, but by the end of the movie, you’ll be sold.
Clueless isn’t the first movie the comes to mind when you think of “classic rom-coms,” but there’s no question that it has deep roots in the genre. Jane Austen, author of Emma (on which the movie is based), was the original rom-com queen. Even if you feel a little odd about the fact Cher — spoiler alert — ends up with her ex-stepbrother Josh, you can’t deny that young Paul Rudd is a treasure.
In this underrated gem, Oliver (Ashton Kutcher) and Emily (Amanda Peet) go from friends with occasional benefits to just friends to lovers over the course of several years. These kinds of relationships rarely work out in real life, which is one reason they’re so fun to watch on screen.
Most people don’t carry flames for their high-school classmates for ten years, but most people don’t look like Ryan Reynolds and Amy Smart. Ryan plays Chris, a former nerd who returns to his hometown to find himself still struggling with feelings for Jamie (Amy Smart), the woman who didn’t return his sentiments in his younger days. Also recommended if you’re still pining for Chris Klein’s glory days — he plays the other guy competing for Jamie’s affection.
When Verona (Maya Rudolph) and Burt (John Krasinski) find out that they’re expecting a child, they can’t decide where to raise it. Their solution? Visit friends and family all over the country to see what might suit their new family. Come for Verona and Burt’s quirky and sweet relationship, stay for an incredible supporting cast that includes Allison Janney, Maggie Gyllenhaal, Carmen Ejogo, and Catherine O’Hara.
A lot of Jennifer Aniston movies get a bad rap, but this one is a gift. Jen plays Polly, a long-lost middle-school classmate of Reuben (Ben Stiller), a buttoned-up insurance underwriter. The pair start dating after Reuben’s acrimonious split from his wife (Debra Messing), and free-spirited Polly shows Reuben how to live a little.
That “you’ve got mail” voice may have gone the way of the 56K modem, but this second Meg Ryan and Tom Hanks team-up remains eternal. She wanted it to be him! She wanted it to be him so badly!
Based on the novel of the same name by Terry McMillan, Waiting to Exhale was lauded for featuring an all-African-American cast led by Whitney Houston, Angela Bassett, Lela Rochon, and the great Loretta Devine. When their lives are rocked by the men in them, the four women realize the power of their friendship (and the power of fire, which is nice if you want to burn your soon-to-be-ex’s things). Fun fact: Waiting to Exhale was directed by Forest Whitaker, who also directed Whitney in the “Exhale (Shoop Shoop)” music video.
What happens when you pair a recently retired hockey player with a figure skating star who’s spoiled AF? A dream team that actually might have a shot at gold at the 1992 Winter Olympics. No, really.
The king of rom-coms Garry Marshall directed real-life lovebirds Goldie Hawn and Kurt Russell in this sweet movie about an obnoxious heiress who falls off her yacht (hence the title) and quite literally into the arms of the local carpenter (Russell) while suffering from a bad case of amnesia.
What’s cuter than a talking baby voiced by Bruce Willis? Watching Kirstie Alley and John Travolta figure out how to take care of said baby in a sweet, sweet film from Amy Heckerling in her pre-Clueless days. The sequels, Look Who’s Talking Too (directed by Heckerling) and Look Who’s Talking Now (produced by Heckerling) are also great fun.
If you break up with someone, do not continue to live with them, no matter what, otherwise you will end up like this movie, basically. Jennifer Aniston and Vince Vaughn play these lovers-turned-roommates, and things go from bad to worse.
Nicolas Cage has a prosthetic hand and Cher has great hair in this over-the-top but delicious film about an Italian-American woman falling for her fiance’s younger brother while the fiance visits his dying mother in Sicily. The movie also popularized Dean Martin’s version of “That’s Amore,” which will now be playing in your head for the rest of the week.
With Amy Schumer’s writing and Judd Apatow’s directing, this film perfectly captures the butterflies and dangers of taking things to the next level, ie. beyond the morning walk of shame. Bill Hader plays the guy Amy seriously falls for, even though her instincts tell her otherwise. LeBron James, Brie Larson, Vanessa Bayer, Tilda Swinton, Daniel Radcliffe, John Cena, and a slew of other famous people are in this.
Pat and Tiffany’s worlds collide all for the better after he’s released from a mental institution and she deals with the fresh death of her husband. They become friends, rehearse for a dance competition, and for some reason, Bradley Cooper can’t stop wearing a garbage bag.
For a chunk of the 2000s, Matthew McConaughey couldn’t stop making romantic comedies, and it was a blessing. In The Wedding Planner, Matthew plays an engaged man who falls for his… WEDDING PLANNER, played by J.Lo, who can’t seem to find “the one” despite her profession. Watch for brilliant performances from the always underrated Bridgette Wilson, Judy Greer, and a BB Justin Chambers, who would star on Grey’s Anatomy four years later.
Would you ever buy a magazine called Composure? Doesn’t matter. Kate Hudson’s Andie Anderson writes for Composure and while she’d much rather tackle
real topics like politics and poverty, her editor wants something juicy, giving birth to the movie’s silly, silly title. The guy she tries to lose (for journalism) is rom-com king Matthew McConaughey, who also has a scheme of his own when he bets he can make any woman fall for him. Look, it’s not hard IRL either, Matthew.