The Best Rom-Coms of All Time

1. When Harry Met Sally (1989)

Director: Rob Reiner | Stars: Billy Crystal, Meg Ryan
Why It’s Iconic: This film invented the “friends-to-lovers” trope and asked the burning question: Can men and women ever just be friends? Over 12 years, Harry and Sally debate love, life, and the merits of deli orders, proving that the best relationships are built on laughter and mutual annoyance.
Memorable Moment: The fake orgasm scene at Katz’s Deli. “I’ll have what she’s having.”

2. Pretty Woman (1990)

Director: Garry Marshall | Stars: Julia Roberts, Richard Gere
Why It’s Iconic: A modern Cinderella story with a twist. Roberts shines as Vivian, a free-spirited escort hired by a billionaire (Gere) for a week—only to teach him that love can’t be bought. It’s cheesy, charming, and the reason red carpet poses exist.
Quote to Remember: “She rescues him right back.”

3. Notting Hill (1999)

Director: Roger Michell | Stars: Julia Roberts, Hugh Grant
Why It’s Iconic: A humble bookstore owner (Grant) falls for the world’s biggest movie star (Roberts) in this whimsical tale of fame vs. normalcy. Bonus points for Grant’s adorably awkward charm and Spike’s roommate antics.
Scene Stealer: “I’m just a girl, standing in front of a boy…”

4. 10 Things I Hate About You (1999)

Director: Gil Junger | Stars: Heath Ledger, Julia Stiles
Why It’s Iconic: A Shakespearean remake (The Taming of the Shrew) set in a ’90s high school. Ledger’s bad-boy serenade (“Can’t Take My Eyes Off You”) and Stiles’ fiery poetry slam cement this as a Gen-X classic.
Legacy: The reason every guy tried to learn guitar in 1999.

5. Bridget Jones’s Diary (2001)

Director: Sharon Maguire | Stars: Renée Zellweger, Colin Firth, Hugh Grant
Why It’s Iconic: Bridget’s cringe-worthy mishaps (see: bunny costume karaoke) and the love triangle between a human golden retriever (Firth) and a charming cad (Grant) are painfully relatable. Plus, that snow fight scene.
Cultural Impact: Spawned a million diary entries starting with “Dear Diary, I’m a disaster.”

6. Love Actually (2003)

Director: Richard Curtis | Stars: Ensemble cast (Hugh Grant, Emma Thompson, Keira Knightley)
Why It’s Iconic: A holiday staple interweaving eight love stories, from prime ministers dancing to “Jump” to silent declarations via cue cards. It’s messy, heartfelt, and proof that “love actually is all around.”
Controversy: Yes, the Joni Mitchell scene still hurts.

7. The Proposal (2009)

Director: Anne Fletcher | Stars: Sandra Bullock, Ryan Reynolds
Why It’s Iconic: A fake-marriage plot between a ruthless editor (Bullock) and her assistant (Reynolds) that’s saved by their crackling chemistry. Also, Betty White as a grandma who dances to “Get Low.”
LOL Moment: Naked hallway collision. Need we say more?

8. Crazy, Stupid, Love (2011)

Director: Glenn Ficarra, John Requa | Stars: Steve Carell, Ryan Gosling, Emma Stone
Why It’s Iconic: A midlife crisis meets a playbook for picking up women. Gosling’s abs and Stone’s “Seriously?!” face steal the show, but the backyard brawl finale is pure chaos.
Life Lesson: Always check if your teenager’s crush is legal.

9. Crazy Rich Asians (2018)

Director: Jon M. Chu | Stars: Constance Wu, Henry Golding
Why It’s Iconic: A groundbreaking rom-com celebrating Asian culture with opulent weddings, mahjong showdowns, and a mother-in-law you’d cross oceans to impress. The perfect blend of glamour and heart.
Standout Scene: The dumpling-making lesson turned emotional gut-punch.

10. To All the Boys I’ve Loved Before (2018)

Director: Susan Johnson | Stars: Lana Condor, Noah Centineo
Why It’s Iconic: A teen rom-com for the Netflix generation. Fake-dating, hot cocoa mix-ups, and Peter Kavinsky’s smile make this a binge-worthy ode to young love.
Viral Moment: The “I like you” yogurt scene.

Honorable Mentions:

• My Big Fat Greek Wedding (2002): Family chaos meets Windex cures.
• 500 Days of Summer (2009): A deconstruction of rom-coms (with a killer soundtrack).
• The Holiday (2006): Cameron Diaz and Kate Winslet swapping homes—and lives.

Why Rom-Coms Matter

Rom-coms aren’t just fluff; they’re mirrors of our hopes and insecurities. They remind us that love is messy, communication is key, and grand gestures don’t have to involve boomboxes (though they’re welcome). Whether you’re team Harry/Sally or Lara Jean/Peter, these films prove that laughter and love are a timeless combo.

Now, grab popcorn, a cozy blanket, and let the marathon begin! What’s your all-time favorite rom-com? Share in the comments below!