THE ULTIMATE GUIDE TO ROMCOMS

By request: my comprehensive list of must-watch romantic comedies, broken out by vibe. You may notice some movies considered “classics” by the general culture are missing. That’s not an accident.

Some of these are standard romantic comedies, others lean toward romantic dramas.

For When You Need to Cry

  • The Notebook (2004), the ultimate. This film is everything.
  • Eternal Sunshine of the Spotless Mind (2004), lil sci-fi adjacent action, a weird one but very, very good.
  • A Star Is Born (2018), they’re all good, but this one has my favorite soundtrack.
  • Love Story (1970), actually barely even a romcom because it’s so sad.
  • Love & Other Drugs (2010), you will cry.
  • P.S. I Love You (2007), probably even on the best day of your life you will still cry a little bit.

For When You Need to Laugh

  • Bridesmaids (2011), duh.
  • Forgetting Sarah Marshall (2008), if you’re a fan of the Jason Segel brand, you’ll enjoy.
  • Bad Teacher (2011), Justin Timberlake in glasses. Hi!
  • Crazy, Stupid, Love (2011), funny with a twist you might not expect the first time around.
  • How to Be Single (2016), four friends with four different approaches to being single. Lots of big names you’ll recognize, overall a fun watch.
  • My Big Fat Greek Wedding (2002), again, duh.

For When You Need a 2000s Classic

  • Love & Basketball (2000), if you haven’t seen it just go watch it, okay?
  • Knocked Up (2007), long live Katherine Heigl, queen of 2000s romcoms.
  • 27 Dresses (2008), continued reign of Katherine.
  • The Ugly Truth (2009), continued, continued reign of Katherine.
  • Hitch (2004), decades before Will went crazy, don’t worry!
  • Miss Congeniality (2000), one of the primary times I’ve liked Sandra Bullock.
  • The Proposal (2009), one of the other times.
  • How to Lose a Guy in 10 Days (2003), the yellooooowww ddrreeessssss, babe!
  • She’s the Man (2006), DUH.
  • Maid in Manhattan (2002), DUH, DUH.
  • Legally Blonde (2001), DUH, DUH, DUH.

For When You Need to Sing Along

  • Enchanted (2007), the pure and sweet Amy Adams!
  • Ella Enchanted (2004), the pure and sweet Anne Hathaway!
  • Mamma Mia! (2008), to the soundtrack of almost every ABBA song ever.
  • Hairspray (2007), one of the few times I’ve fully preferred a remake.

For When You Need to Turn Your Brain Off

  • Isn’t It Romantic (2019), a parody that still turned out so sweet.
  • Set It Up (2018), I think Glen Powell’s first romcom? Very cute.
  • Hit Man (2023), imo solidified Glen Powell’s “epic romcom lead” status.
  • 17 Again (2009), Zac Efron with the most 2009 possible haircut.
  • The Prince & Me (2004), fulfilling every girl’s dream that their casual crush is secretly a rich prince of some foreign country no one has ever heard of.
  • When We First Met (2018), funny moments, sweet ending.
  • Anyone But You (2023), just like hot people talking and arguing? Not acting well, but talking and arguing.

For When You Need a High School Story (lmao)

  • The Princess Diaries (2004), rags to riches, except the “rags” are an extremely cool San Fransisco loft?
  • To All the Boys I’ve Loved Before (2018), story & screenplay by Jenny Han!
  • Easy A (2010), creative twist on a classic story — did you read “The Scarlet Letter” in high school? If so you’ll probs like this version better.
  • 10 Things I Hate About You (1999), also based on a classic tale (Shakespeare’s “The Taming of the Shrew”). Julia Stiles reading that poem is everything to me.

For When You Need a Cheesy RomCom That’s Still Low Key a Good movie

  • Leap Year (2010), a little silly but pretty good!
  • About Time (2013), Rachel McAdams, time travel, kind of dumb but just give in!
  • The Photograph (2020), transcending timelines for a cross-generational love story.
  • As Good as It Gets (1997), Jack Nicholson and Helen Hunt won Best Actor and Best Actress for their roles here.

For When You Need a RomCom Where Romance is Simply a Fringe Benefit of the Main Character’s Journey to Self-Realization & Acceptance

  • Confessions of a Shopaholic (2009), an absolute gem. Made me want to learn Finnish.
  • 13 Going on 30 (2004), weird if you think about it too hard, so just don’t!
  • Eat Pray Love (2010), a standard must-watch whether you like it or not.
  • How Stella Got Her Groove Back (1998), hasn’t been seen enough. Taye Diggs, hi!
  • Legally Blonde (2001), adding this one in a second category, because obviously.

For When You Need a RomCom That Transcends RomCom Status to Become an Actually, Truly Good Movie

  • Palm Springs (2020), excellent movie with a time loop feature.
  • Notting Hill (1999), a classic for a reason, babe! Hugh is just a boy.
  • Materialists (2025), new addition to my rewatch roster.
  • Crazy Rich Asians (2018), I stand by this being a 4-star film.
  • Punch-Drunk Love (2002), a PTA standard must-watch.

For When You Need an LGBT+ Romance

  • But I’m A Cheerleader (1999), Natasha Lyonne at a scared straight boot camp.
  • Crush (2022), very, very cheesy (Disney channel vibes) high school romcom.
  • Fire Island (2022), a modern retelling of Jane Austen’s “Pride and Prejudice.”
  • Love, Simon (2018), another high school coming out story.
  • Y Tu Mama También (2001), n-a-u-g-h-t-y. Diego Luna & Gael García Bernal. That’s all!

For When You Need a True Classic of the Genre

  • ‘Pillow Talk’ (1959), Doris Day, an icon, and Rock Hudson — a classic of 50’s cinema.
  • Breakfast at Tiffany’s (1961), Audrey Hepburn will teach you what a movie should be!
  • Roman Holiday (1953), see above re: Audrey.
  • The Philadelphia Story (1940), About 10 times a week, I say the phrase “As originally, and most beautifully planned,” exactly the way Katherine Hepburn says it in this movie.

For When You Need a Christmas RomCom

  • The Holiday (2006), we watch annually to see Jude Law’s look. You know the one. (Bonus reading: Cosmo’s “Why Jude Law’s Character in The Holiday is the Best Man to Ever Exist”)
  • Four Christmases (2004), a forgotten-about gem that needs to reappear in the cultural zeitgeist.
  • The Family Stone (2005), you have never hated Carrie Bradshaw like this — but don’t worry, she’ll win you back.
  • Happiest Season (2020), she’s a little sad, but worth a watch.
  • Holidate (2020), could also live in the “When You Need to Turn Your Brain Off” category.
  • The Preacher’s Wife (1996), maybe not technically a romcom, but a good romance storyline.

Bonus: For When You Still Need More

  • Celeste & Jesse Forever (2012), I don’t know how to classify this one but it’s pretty good.
  • 500 Days of Summer (2009), also don’t know how to classify but an obvious must-watch.
  • Bridget Jones’s Diary (2001), the world’s fakest British accent, but it’s fine!
  • The Bodyguard (1992), Whitney Houston, baby! Probably technically not a romcom, but a truly classic romance tale.

Bonus: For When You Want to Watch Someone Choose Between Two Men (TSITP Vibes lol)

  • The Notebook (2004)
  • Materialists (2025)
  • Past Lives (2023), Oscar nominated for Best Picture.
  • Moonstruck (1987), Cher, my darling!
  • Sabrina (1954) Audrey and Humphrey Bogart. He’s way too old, it’s fine.

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