70 Romantic Comedies From The Last 15 Years, Ranked
You’re going to be so mad at me when you read this list! It’s okay. I’m prepared. But I do stand by my rankings. I’m passionate! I’m convinced! Now tell me how wrong I am in the comments.
My rankings are for American movies from 2000-2015 that are romantic comedies. Romantic movies that don’t even try to be funny are out of the running (Example: “No Reservations”). Funny movies in which romance isn’t the main point don’t count either. Litmus test: It should be reasonable that the movie poster has both romantic leads on the cover. If it wouldn’t make sense to put one of them on, it’s probably not a rom-com. (Example: “High Fidelity” is about John Cusack’s personal journey more than him getting back in the with the blonde.)
NOTE: I have seen A LOT of rom-coms—and I watched and rewatched the trailer for every movie I ranked—but it is not possible to have seen all of these movies and also be a functioning member of this barely-functioning society. For the handful I didn’t see, I sought reviews from trusted friends and read reviews online. So yeah, it’s not a perfect science. (IT’S NOT A PERFECT SCIENCE: HE is a theology professor in upstate New York. SHE is a hot shot microbiologist in the big city. Can they compromise on God, the origin of man, and the purpose of existence in the name of love? Also, what will they do about his cat allergy? Fund my movie and find out!)
Here are the rankings from worst to best:
70. SUMMER CATCH (2001) starring Freddie Prinze Jr., Jessica Biel, and everything wrong with romantic comedies and this dumb planet’s treatment of women. I’d actually like to think we’ve come a long way since 2001.
69. JUST MY LUCK (2006) starring Lindsay Lohan, Chris Pine, and the dumbest premise in the world.
68. DOWN TO YOU (2000) starring Freddie Prinze Jr., Julia Stiles, and I mean just really bad everything.
67. MONSTER-IN-LAW (2005) starring Jennifer Lopez, Michael Vartan and Jane Fonda, being angry for no reason.
66. GOOD LUCK CHUCK (2007) starring Dane Cook’s gross dumb face and Jessica Alba’s empty acting and a plot that’s both stupid and offensive!
65. CHASING LIBERTY (2004) starring Mandy Moore as the president’s daughter, Matthew Goode as a secret service agent and aedritrjawer sorry I fell asleep.
64. NEW YEAR’S EVE (2011) starring everyone who has ever taken an acting class, and one writer making a deal with the devil.
63. VALENTINE’S DAY (2010) starring a million people and nooooooo gooooood jokes. Just write a real joke! Come on!
62. FOOL’S GOLD (2008) starring Kate Hudson and Matthew McConaughey. You could not pay me to watch this movie.
61. SHE’S OUT OF MY LEAGUE (2010) starring Jay Baruchel, Alice Eve, and a premise that wipes out millions of people’s hard work to mitigate sexism and racism. Women should be rated on a scale of 1 to 10! We are only as good as we look! We must look blonde and thin! Isn’t this FUNNY?!
60. LICENSE TO WED (2007) starring John Krasinski, Mandy Moore, and a very poor use of Robin Williams.
59. FOUR CHRISTMASES (2008) starring Reese Witherspoon and Vince Vaughn and BOREDOM.
58. THE BACK-UP PLAN (2010) starring Jennifer Lopez, Alex O’Loughlin, and a pregnancy that’s supposed to scare away her dream guy or whatever.
57. ALOHA (2015) starring Emma Stone, Bradley Cooper, Rachel McAdams, John Krasinski and nine plots that don’t make any sense together.
56. HE’S JUST NOT THAT INTO YOU (2009) starring Jennifer Aniston, Ginnifer Goodwin, Jennifer Connelly, Ben Affleck, Kevin Connolly, Justin Long, Bradley Cooper, Scarlett Johansson, Drew Barrymore and despite all these great people, barf forever.
55. ZACH AND MIRI MAKE A PORNO (2008) starring Seth Rogen, Elizabeth Banks, and in the words of my sister “the need to grip a table very hard to handle how bad and uncomfortable this movie is.”
54. THE PRINCE AND ME (2004) starring Julia Stiles and Luke Mably. I love Wisconsin more than any place on the planet and I still can’t get into this movie.
53. THE UGLY TRUTH (2009) starring Katherine Heigl, Gerard Butler, and infuriating stereotypes.
52. JUST MARRIED (2003) starring Brittany Murphy, Ashton Kutcher, and a lot of slipping on banana peel type jokes.
51. LOSER (2000) starring Jason Biggs, Mena Suvari, and a loose plot about both leads being outcasts in college?
50. COUPLES RETREAT (2009) starring Vince Vaughn, Kristen Bell, Kristen Davis, Malin Akerman, Jon Favreau, Faizon Love, Kali Hawk, Jason Bateman, and snooze-inducing cliches about relationship problems.
49. WHAT’S YOUR NUMBER (2011) starring the supremely annoying Anna Faris and Chris Evans in a predictable barfathon.
48. WHAT HAPPENS IN VEGAS (2008) starring Ashton Kutcher, Cameron Diaz, Lake Bell, Rob Corddry, and an actually-clever plot with sad, sad, sad writing.
47. WHEN IN ROME (2010) starring Kristen Bell and Josh Duhamel. In Rome! Blurf.
46. LIFE AS WE KNOW IT (2010) starring Katherine Heigl, Josh Duhamel, a baby who poops constantly, and a dead couple. :/
45. LEAP YEAR (2010) starring Amy Adams, Matthew Goode, the misuse of comedy god Adam Scott, placeholder jokes that never got rewritten, and the Irish countryside.
44. FAILURE TO LAUNCH (2006) starring Matthew McConaughey and Sarah Jessica Parker and a plot that doesn’t make any sense AT ALLLLLLLLLL.
43. BLENDED (2014) starring Adam Sandler, Drew Barrymore, and stereotypes about Africa.
42. KILLERS (2010) starring Ashton Kutcher and Katherine Heigl as an accidental assassin.
41. MAID IN MANHATTAN (2002) starring Jennifer Lopez and Ralph Fiennes. Derf, whatever.
40. ALONG CAME POLLY (2004) starring Ben Stiller, Jennifer Aniston, and spicy food that makes Ben Stiller poop! Do you get it? It’s deep comedy!
39. A LOT LIKE LOVE (2005) starring Ashton Kutcher, Amanda Peet, and bad timing. Meh.
38. FEVER PITCH (2005) starring THE BOSTON RED SOXXXXXXX. GET IT????? HE LOVES BASEBALLLLLLLLLLL.
37. WIMBLEDON (2004) starring Kirsten Dunst, a British potato, and a very boring plot.
36. MUSIC AND LYRICS (2007) starring Drew Barrymore, Hugh Grant and a piano.
35. JUST FRIENDS (2005) starring Ryan Reynolds, Chris Kline, Amy Smart, Anna Faris, and like two plots in one. This movie could have used a storyline makeover.
34. MY BEST FRIEND’S GIRL (2008) starring Kate Hudson, Dane Cook and Jason Biggs. Pleh?
33. THE BREAK-UP (2006) starring Vince Vaughn, Jennifer Aniston, and relationship problems that are actually kind of relatable and thus depressing.
32. JUST GO WITH IT (2011) starring Adam Sandler, Jennifer Aniston and Brooklyn Decker’s boobs.
31. 500 DAYS OF SUMMER (2009) starring Joseph Gordon-Levitt and Zooey Deschanel’s bangs. This movie isn’t very good. You just think it is because you know who The Smiths are and you’ve always wanted covered buttons on your wedding dress, too.
30. THE WEDDING PLANNER (2001) starring Jennifer Lopez, Matthew McConaughey and perpetual rom com best friend Judy Greer. JUDY I WANT TO BE YOUR SIDEKICK. This movie is so cheesy, but it doesn’t get dropped lower because it’s also so old and set the tone for the modern version of the genre, IMHO.
29. SWEET HOME ALABAMA (2002) starring Reese Witherspoon, Patrick Dempsy, Josh Lucas and THE SOUTH!
28. NO STRINGS ATTACHED (2011) starring Natalie Portman as a boring doctor and Ashton Kutcher as a paper doll man.
27. HOW TO LOSE A GUY IN 10 DAYS (2003) starring Matthew McConaughey and Kate Hudson being annoying on purpose. So meta.
26. THE WEDDING DATE (2005) starring Dermot Mulroney, Debra Messing and really bad hair and makeup.
25. FRIENDS WITH BENEFITS (2011) starring Justin Timberlake, Mila Kunis, and Patricia Clarkson as Mila’s mom, and I think Patricia Clarkson should be president in real life. (Also this movie is funnier than the other movie just like it.)
24. 50 FIRST DATES (2004) starring Drew Barrymore and Adam Vomit Sandler. Still, cute plot and decent execution!
23. THIS MEANS WAR (2012) starring Reese Witherspoon, Chris Pine, Tom Hardy, Tom Hardy’s pillow-y lips and explosions.
22. KNOCKED UP (2007) starring Katherine Heigl, Seth Rogen, and the rise of the man child, which I would like to take this opportunity to barf all over.
21. LOVE ACTUALLY (2003) starring every person on the planet. I don’t get why this movie is a big deal. It does not charm me so much.
20. MADE OF HONOR (2008) starring Patrick Dempsy and Michelle Monaghan. I can’t help but like it when a guy is a maid of honor.
19. WHAT WOMEN WANT (2000) starring Mel Gibson, Helen Hunt, and Mel’s ability to read women’s minds. Just pretend Mel Gibson is anyone else and this movie becomes kinda good.
18. HITCH (2005) starring Will Smith, Eva Mendez, and my guilty pleasure actor, Kevin James.
17. WANDERLUST (2012) starring Jennifer Aniston, Paul Rudd, and Tom’s All Natural Deodorant.
16. THE FIVE YEAR ENGAGEMENT (2012) starring Jason Segel, and Emily Blunt. For a really long time. Too long, but funny and good!
15. THE HOLIDAY (2006) starring Kate Winslet, Cameron Diaz, Jude Law and Jack Black. Cute but not too funny.
14. WIN A DATE WITH TAD HAMILTON (2004) starring Kate Bosworth, Josh Duhamel, Topher Grace and Ginnifer Goodwin as the frumpy friend even though she’s a god-damn-dorable!
13. SOMETHING BORROWED (2011) starring Kate Hudson, Ginnifer Goodwin, John Krasinski, Colin Egglesfield. Props for having an ending that could go a couple of ways.
12. 13 GOING ON 30 (2004) starring Jennifer Garner, Mark Ruffalo and <3 Judy Greer <3. I hate to break it to you, but I just rewatched it, and this movie doesn’t hold up as well as you’d think. Wah.
11. 27 DRESSES (2008) starring Katherine Hiegl with brown hair, James Marsden, Malin Akerman, Ed Burns, and my favorite actress Judy Greer(!!!).
10. FRIENDS WITH KIDS (2011) starring Jennifer Westfeldt and Adam Scott. I like this one a whole lot. You all probably do, too.
9. NICK AND NORAH’S INFINITE PLAYLIST (2008) starring Michael Cera and Kat Dennings. Truth: I have never wanted to see this movie and still don’t, but everyone who I asked about it RAVES ENDLESSLY. Did I get this ranking right?
8. THE PROPOSAL (2009) starring Sandra Bullock, Ryan Reynolds, Betty White grabbing Sandra’s boobs, and ALASKA!
7. CRAZY, STUPID LOVE (2011) starring Steve Carrell, Ryan Gosling, Julianne Moore, Emma Stone, and age-appropriate-ish relationships! The charm is in the details in this movie. They get it right.
6. SHALLOW HAL (2001) starring Jack Black and Gwenyth Paltrow. Great movie, but it’s too mean to fat people when you rewatch it.
5. FORGETTING SARAH MARSHALL (2008) starring Kristen Bell, Mila Kunis, Jason Segel, and JASON SEGEL’S DICK, YO! I think a lot of people see this as the best rom-com. I suspect we feel that way because boys also like this movie. I don’t think that automatically qualifies it as THE BEST. But it is very funny and good!
4. BRIDGET JONES’S DIARY (2001) starring Renee Zelwegger, Colin Firth, and Hugh Grant. Of course single women in their 30s aren’t saddos, but this movie is so so so so funny.
3. TRAINWRECK (2015) starring Amy Schumer, Bill Hader, and despite being a wonderful, hilarious movie that challenges stereotypes, way too much LeBron James.
2. THE 40-YEAR-OLD VIRGIN (2005) starring Steve Carrell and Catherine Keener. Wonderful!
1. MY BIG FAT GREEK WEDDING (2002) starring Nia Vardolas and John Corbett. Remember travel agents?! Aha. This movie is aces!
OBVIOUS CHILD (2014), because, while I wanted to put this Jenny Slate movie on the list, it’s more about Jenny’s personal growth than her relationship. Such a great movie, though.
GOING THE DISTANCE (2010) is disqualified because the writer of this piece had a crush on the writer of that movie and cannot judge with a fair mind. (We met on Twitter, never IRL, but I was so single at the time that it really meant something to me.)
IT’S COMPLICATED (2009) & SOMETHING’S GOTTA GIVE (2003) are out of the running because I feel like I can’t properly judge these Nancy Meyers movies because they aren’t for me. All the jokes seem weak to me, but 60-year-old me might be laughing till I puke.