The Worst Romantic Comedies That Are Actually Great


There is no such thing as a bad romantic comedy. Now, I know what you’re thinking: You’ve watched plenty of rom-coms that are so cringe-inducing you want to crawl into a hole and die out of embarrassment for everyone involved. I’ve experienced that same feeling (talkin’ about you, The Kissing Booth)! But to that I also say this: Even when rom-coms are objectively terrible or flop — and plenty of them have been objectively terrible and flopped over the years — they still have the impressive ability to inspire feelings of warmth and happiness in all of us. Therefore, they can’t be bad.

The recognizable formula people complain about every time a new rom-com is released is exactly what we’re all seeking out because it makes us believe in true love and the promise of a happily ever after. We want to believe, even for a little while, that there’s a world in which Matthew Goode will love us too. The narrative beats might be familiar, and clichés likely abound, but the desire to fall in love and be loved in return is universal, meaning romance never goes out of style. The fact that these films manipulate our emotions through contrived plots is arguably part of the point. So, the fact that the journey to get to the destination is not always well-written (or well-acted or well-directed) doesn’t really matter as long as the films in question still possess the ability to make the region where our hearts should be feel a little less cold and empty. Plus, sometimes, when a movie is really bad, you just can’t look away.

The Best Romantic Movies for Valentine’s Day on Netflix, Hulu, Disney+, and Amazon Prime Video

So, in honor of Valentine’s Day and bad rom-coms everywhere, I give you a list of truly terrible movies that are actually totally great, and definitely worth your love this holiday (and every day).

Editor’s Note: While this list is obviously in no way complete, The Wedding Planner, Sweet Home Alabama, and How to Lose a Guy in 10 Days are actually great rom-coms and I will not allow you to pretend otherwise, so don’t even think about asking where they are.

(Disclosure: Links to retailers may earn money to support our work.)

Julia Stiles and Freddie Prinze Jr., <em>Down to You</em>Julia Stiles and Freddie Prinze Jr., Down to You

1. Leap Year (2010)
Watch it on: Amazon Prime (rent or purchase), Vudu (rent or purchase)
Amy Adams and Matthew Goode star in this film about a woman who travels to Ireland to propose to her long-time boyfriend on Leap Day because of a supposed tradition that says men can’t deny a woman’s proposal on said day. However, when her plans are thwarted, she meets an Irish innkeeper, and she falls for him instead.

2. Down to You (2000)
Watch it on: HBO, Hulu (with HBO add-on), Amazon Prime (rent or purchase; with HBO add-on), Vudu (rent or purchase)
There was a point in time in which every teen was in love with Freddie Prinze Jr., and that was right around the time he starred alongside Julia Stiles in this film about two college students who meet and fall in love a bit too early. In addition to also starring Henry Winkler, Ashton Kutcher, Rosario Dawson, and Selma Blair, the film also taught all of us why you should never drink shampoo.

3. Drive Me Crazy (1999)
Watch it on: Amazon Prime (rent or purchase), Vudu (rent or purchase)
Before he became Entourage‘s resident movie star Vincent Chase, Adrian Grenier starred in Drive Me Crazy opposite Melissa Joan Hart as two neighbors who scheme to fake date each other in order to attract the attention of the people they really want to date. I’ll let you figure out what happens next.

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4. You’ve Got Mail (1998)
Watch it on: Amazon Prime (rent or purchase), Vudu (rent or purchase)
It’s hard to deny the fact Tom Hanks catfished Meg Ryan in You’ve Got Mail, so even if it is considered a classic rom-com with a stellar supporting performance from a truly great dog, it didn’t age well. Regardless, now we all know how to spell fox and recognize that supporting independent bookstores is very important!

5. Just Married (2003)
Watch it on: Hulu, Amazon Prime (rent or purchase), Vudu (rent or purchase)
Ashton Kutcher and the late Brittany Murphy star in this rom-com as Tom and Sarah, a young couple from different worlds who marry quickly and discover, while on their honeymoon, that marriage needs a bit more than love to work. Tone deaf and dumb, this film will still make you wonder if we haven’t really appreciated Ashton Kutcher enough.

6. Fever Pitch (2005)
Watch it on: Amazon Prime (rent or purchase), Vudu (rent or purchase)
Yes, this is a rom-com starring Jimmy Fallon, the man who wasn’t able to make it through most sketches on Saturday Night Live without breaking. And yes, it’s about a Red Sox fan who struggles to put his girlfriend (Drew Barrymore) above his love for baseball. Honestly, the worst thing about this movie is that it will remind you the Red Sox have won three additional World Series since it came out.

7. Chasing Liberty (2004)
Watch it on: Amazon Prime (rent or purchase), Vudu (rent or purchase)
It’s a tale as old as time: Mandy Moore is the daughter of the president who unknowingly falls for a Secret Service agent, played by Matthew Goode, who has been assigned to protect her without her knowledge. Happens to me every single day.

8. Serendipity (2001)
Watch it on: Starz, Hulu (with a Starz add-on), Amazon Prime (rent or purchase; with Starz add-on), Vudu (rent or purchase)
Fate plays a major role in this John Cusack and Kate Beckinsale rom-com that is jump-started when both attempt to buy the same pair of gloves. After putting their respective phone numbers on a $5 bill and inside a book, the two go their separate ways with the knowledge that if they find the other’s number, they’re meant to be. This film would not be made in 2020 because putting your phone number out into the world is just asking for bad things to happen to you.

<em>Never Been Kissed</em>Never Been Kissed

9. Never Been Kissed (1999)
Watch it on: Disney+, Amazon Prime (rent or purchase), Vudu (rent or purchase)
Drew Barrymore portrays a copy editor who has never had a real relationship but falls in love with a pre-Alias Michael Vartan, who portrays a hockey-loving English teacher, when she goes undercover at the local high school. Does this make any sense? Not really! But it might make you understand the difference between nauseous and nauseated.

10. The Ugly Truth (2009)
Watch it on: Netflix, Amazon Prime (rent or purchase), Vudu (rent or purchase)
Katherine Heigl was at the height of her fame when she starred in The Ugly Truth as Abby, a morning show producer who inevitably falls for Gerard Butler‘s Mike, a crass TV host who coaches her through a separate relationship until she realizes the guy only liked her for the woman he thought she was.

11. Simply Irresistible (1999)
Watch it on: Amazon Prime (rent or purchase), Vudu (rent)
This movie starring Sarah Michelle Gellar features a magic crab as a major plot point. I honestly don’t think I need to say much more than this.

12. Catch and Release (2007)
Watch it on: IMDb TV (free with ads), Amazon Prime (rent or purchase), Vudu (rent or purchase)
After Jennifer Garner‘s fiancé dies, she takes comfort in his friends, eventually falling for his best friend, which is understandable because his best friend is played by Timothy Olyphant. We should all be so lucky.

13. Because I Said So (2007)
Watch it on: Starz, Hulu (with Starz add-on), Amazon Prime (rent or purchase; with Starz add-on), Vudu (rent or purchase)
Diane Keaton plays an overbearing mother who is worried her youngest daughter, Mandy Moore‘s Milly, will never find true love, so she takes out an ad looking for a man to date her daughter in this problematic but sweet (and I’m not just saying that because Milly is a baker) rom-com that also stars Tom Everett Scott and Gabriel Macht.

14. Penelope (2007)
Watch it on: Vudu (free with ads; rent or purchase), Tubi (free with ads), Amazon Prime (rent or purchase)
Disclosure: Penelope is not nearly as bad as most of the films on this list and it gets away with a lot because it’s a cute fairy tale. In it, Christina Ricci plays Penelope, a young woman cursed with a pig snout, a storyline that reminds us beauty is only skin deep, in the eye of the beholder, etc. Meanwhile, James McAvoy is so charming it’s honestly not fair to the rest of the world.

15. The Object of My Affection (1998)
Watch it on: HBO, Hulu (with HBO add-on), Amazon Prime (rent or purchase; with HBO add-on), Vudu (rent or purchase)
Jennifer Aniston and Paul Rudd star as best friends in this rom-com, proving that our own lives really are unfair. Things get complicated, though, when Aniston’s pregnant Nina develops feelings for Rudd’s George, who is a gay man.

16. Wimbledon (2004)
Watch it on: Hulu (with Cinemax add-on), Amazon Prime (rent or purchase; with Cinemax add-on), Vudu (rent or purchase)
Kirsten Dunst stars as an up-and-coming tennis pro who falls for a veteran player (Paul Bettany) who can’t keep up anymore in this rom-com that will make you want to finally figure out tennis’ confusing scoring system.

17. Win a Date With Tad Hamilton! (2004)
Watch it on: Amazon Prime (rent or purchase), Vudu (rent or purchase)
Kate Bosworth portrays a woman who wins a date with a hot movie star trying to rehab his image (Josh Duhamel) in this West Virginia-set rom-com. However, she doesn’t realize the love of her life, her best friend Pete (Topher Grace), has been there the whole time. Honestly, we all overlooked Topher Grace as a romantic leading man, and we should be ashamed.

Source : TVGuide