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The worst romantic comedy pairings of all time
Columbia Pictures

The worst romantic comedy pairings of all time

We all know that most romantic comedies aren't perfect, especially those completely miscast. Here are some of the worst rom-com pairings of all time.

 
1 of 20

Meg Ryan & Hugh Jackman, 'Kate & Leopold'

Meg Ryan & Hugh Jackman, 'Kate & Leopold'
Miramax

I want to preface this by saying that casting Hugh Jackman in Kate & Leopold wasn't the problem here. The decision to cast Meg Ryan to play opposite Jackman is what baffles me. Don't get me wrong. She is a wonderful actress. It's just that this particular pairing doesn't quite make sense to me.

 
2 of 20

Anne Hathaway & Chris Pratt, 'Bride Wars'

Anne Hathaway & Chris Pratt, 'Bride Wars'
Walt Disney Studios

While I realize that Anne Hathaway's and Chris Pratt's characters are not the main focus of Bride Wars, I still hate everything about it. Their incompatibility makes sense, I suppose, given the film's ending, but I think they still could've gone with someone else.

 
3 of 20

Sarah Jessica Parker & Matthew McConaughey, 'Failure to Launch'

Sarah Jessica Parker & Matthew McConaughey, 'Failure to Launch'
Paramount Pictures

Blame it on the script or Sarah Jessica Parker and Matthew McConaughey's lack of chemistry, but Failure to Launch wasn't it. We can all agree that these actors are a delight to watch individually, but together, it just didn't translate. As difficult as it is to imagine McConaughey, the god of 2000s rom-coms, not vibing with any leading lady, this film sure found a way.

 
4 of 20

Matthew Perry & Elizabeth Hurley, 'Serving Sara'

Matthew Perry & Elizabeth Hurley, 'Serving Sara'
Paramount Pictures

Serving Sara is bad, but I’m hesitant to rip into it considering what Matthew Perry was going through at the time. That said, with a subpar script and a lack of chemistry between Perry and Elizabeth Hurley, there wasn't much that could save this film.

 
5 of 20

Katherine Heigl & Seth Rogen, 'Knocked Up'

Katherine Heigl & Seth Rogen, 'Knocked Up'
Universal Pictures

Of all the terrible romantic comedy pairings, Katherine Heigl and Seth Rogen in Knocked Up are not the worst, given the film's success. However, I think if Heigl had played the character more to her liking (as she had previously expressed her distaste for how women were portrayed in the movie), it would have made it easier to root for her and Rogen's characters to be together.

 
6 of 20

Kelly Clarkson & Justin Guarini, 'From Justin to Kelly'

Kelly Clarkson & Justin Guarini, 'From Justin to Kelly'
Walt Disney Studios

Do I even need to explain? American Idol's season one winner, Kelly Clarkson, wanted no part of this, and we don't blame her. Unfortunately, she and runner-up Justin Guarini were contractually obligated to do this film together because, I guess, the show's creator hated them. Thankfully, this fever dream of a movie was only a one-time thing.

 
7 of 20

Jessica Alba & Dane Cook, 'Good Luck Chuck'

Jessica Alba & Dane Cook, 'Good Luck Chuck'
Lionsgate

Let's be honest. Good Luck Chuck was as good as any Dane Cook movie possibly can be; it'll make you laugh every now and then, but at the end of the day, it's just not very memorable. The script was meh at best, and the chemistry between Cook and Jessica Alba wasn't there.

 
8 of 20

Ben Affleck & Jennifer Lopez, 'Gigli'

Ben Affleck & Jennifer Lopez, 'Gigli'
Sony Pictures

You had to know Ben and Jen were going to make the list. Ben Affleck and Jennifer Lopez couldn't make it work on screen in Gigli or off-screen, no matter how many times they may try. It's no surprise the film won numerous Golden Raspberry Awards, including "Worst Screen Couple."

 
9 of 20

Sandra Bullock & Bradley Cooper, 'All About Steve'

Sandra Bullock & Bradley Cooper, 'All About Steve'
Walt Disney Studios

I'm not sure whether or not this was a poor rom-com pairing or if All About Steve was just that bad of a script. Regardless, neither Sandra Bullock nor Bradley Cooper could save the film, further validating their Razzie Award win for "Worst Screen Couple" that year.

 
10 of 20

Reese Witherspoon & Ashton Kutcher, 'Your Place or Mine'

Reese Witherspoon & Ashton Kutcher, 'Your Place or Mine'
Netflix

I didn't necessarily think Your Place or Mine would be the best rom-com I've ever seen, but as a fan of Reese Witherspoon and Ashton Kutcher, I certainly had higher hopes for them. The actors' real-life friendship definitely comes across on screen, but when it comes to a romantic connection, their characters should have stayed just friends.

 
11 of 20

Jennifer Aniston & Gerard Butler, 'The Bounty Hunter'

Jennifer Aniston & Gerard Butler, 'The Bounty Hunter'
Sony Pictures

I don't hate The Bounty Hunter as much as other people seem to, but I agree that Jennifer Aniston and Gerard Butler do not make the best on-screen couple. Jen, you're perfect. Don't change a thing. Gerard Butler, on the other hand, has to go.

 
12 of 20

Ralph Fiennes & Jennifer Lopez, 'Maid in Manhattan'

Ralph Fiennes & Jennifer Lopez, 'Maid in Manhattan'
Sony Pictures

Although Maid in Manhattan is considered a classic comfort movie, the relationship between the characters, played by esteemed dramatic actor Ralph Fiennes and singer Jennifer Lopez, is not all that believable. That said, I will still be watching it when in need of a pick-me-up.

 
13 of 20

Bill Pullman & Ellen DeGeneres, 'Mr. Wrong'

Bill Pullman & Ellen DeGeneres, 'Mr. Wrong'
Walt Disney Studios

I don't even need to see Mr. Wrong to know just how wrong Ellen DeGeneres and Bill Pullman are together. The fact that this movie even exists is unbelievable and feels like something out of an alternate universe.

 
14 of 20

Hugh Grant & Sarah Jessica Parker, 'Did You Hear About the Morgans?'

Hugh Grant & Sarah Jessica Parker, 'Did You Hear About the Morgans?'
Sony Pictures

The only believable thing about Hugh Grant's and Sarah Jessica Parker's characters in Did You Hear About the Morgans? is that they were getting a divorce. I'll never understand what brought these two together in the first place. While we love to see Hugh Grant in a rom-com, he and SJP just weren't a match.

 
15 of 20

Madonna & Adriano Giannini, 'Swept Away'

Madonna & Adriano Giannini, 'Swept Away'
Sony Pictures

Remakes are tricky, and casting Madonna in Swept Away was a risk that did not pay off. Her acting is so terrible that she won the Razzie for "Worst Actress" as well as "Worst Supporting Actress" for another film that same year. The idea of these characters getting together made no sense at all, and the film has more than enough Razzies to prove it, including "Worst Screen Couple."

 
16 of 20

Owen Wilson & Jennifer Lopez, 'Marry Me'

Owen Wilson & Jennifer Lopez, 'Marry Me'
Universal Pictures

I thought I had seen it all, and then they went and made Owen Wilson the love interest in a Jennifer Lopez movie. While J. Lo isn't my favorite, I believe she could've had better chemistry with someone who isn't Owen Wilson. He's a fantastic actor, but these two as a couple in Marry Me just didn't work.

 
17 of 20

Julia Roberts & Nick Nolte, 'I Love Trouble'

Julia Roberts & Nick Nolte, 'I Love Trouble'
Walt Disney Studios

I need to know whose idea it was to pair Julia Roberts and Nick Nolte in a romantic comedy action movie because there's no way Nancy Meyers pushed for that. Yes, I Love Trouble is a Nancy Meyers film. The only thing holding them together is the actors' painfully obvious disdain for one another.

 
18 of 20

Renée Zellweger & Chris O'Donnell, 'The Bachelor'

Renée Zellweger & Chris O'Donnell, 'The Bachelor'
Warner Bros. Pictures

The Bachelor is another remake that just didn't pan out. Not only did the story not make much sense, but Renée Zellweger and Chris O'Donnell weren't very convincing as a couple. Oh, and Mariah Carey was there for some reason.

 
19 of 20

Jonah Hill & Lauren London, 'You People'

Jonah Hill & Lauren London, 'You People'
Netflix

I really wanted to like this movie but found it difficult to laugh through the many uncomfortable moments of You People. Jonah Hill and Lauren London might have actually been able to make it work had the storyline not revolved solely around making people cringe.

 
20 of 20

Nina Dobrev & Jimmy Yang, 'Love Hard'

Nina Dobrev & Jimmy Yang, 'Love Hard'
Netflix

Sure, Nina Dobrev and Jimmy Yang in Love Hard are an unlikely pair, and it wouldn't necessarily be a problem if the two had chemistry, but that's not the worst part of this movie. I just have a hard time believing that any woman would actually end up falling for a man after catfishing her, even during the holidays.

Shelby Weimer

Shelby Weimer is a content creator and comedy writer based in Brooklyn, New York, who grew up watching and quoting way too many movies, inevitably leading her to earn a film degree (oh no). She has worked in just about every role in the entertainment industry and has written for various online publications, including Screen Rant. When she isn’t writing and creating content, she’s most likely listening to her music a little too loud or tending to her cat/god of mischief, Loki

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