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Hollywood's Chemical Romance: The Best and Worst Romantic Comedy Pairings of All Time

Updated on May 12, 2012
Breakfast at Tiffany's movie poster
Breakfast at Tiffany's movie poster
Blind Date movie poster
Blind Date movie poster
The War of the Roses movie poster
The War of the Roses movie poster
I Love Trouble movie poster
I Love Trouble movie poster
Pretty Woman movie poster
Pretty Woman movie poster
Gigli movie poster
Gigli movie poster

When it comes to chemistry, many couples either live by it or fail miserably without it. No one can specifically determine what makes certain people meant for each other and others want to kill each other. The same can be said in Hollywood. No amount of writing can overlook an onscreen couple's attraction or lack thereof. It's either movie magic or a tragic waste of money for ticketholders.

Here's a list five romantic comedies pairings that sizzled and deserved an encore. Of course, no list wouldn't be complete without examining the other end of the spectrum. Here are five pairings that just simply didn't add up due to casting and other various reasons. Read through to get an idea what to watch on Valentine's Day with your loved one.

Perfect Love Matches

Katharine Hepburn and Cary Grant in The Philadelphia Story (1940) - For many moviegoers, the most commonly recognized Hepburn pairing was with her real life love interest Spencer Tracy than Grant. Most of her work with Grant was released when Hepburn was labeled "Box Office Poison" by Hollywood after a few movie misfires. What made this Story work was that Grant and Hepburn got to play their signature roles: Grant as the charmer and Hepburn as the cynic. Grant and Hepburn played a divorced couple that came together for her wedding to a mismatched suitor. It only took a crazy weekend, a drunken misunderstanding and a hangover to realize they were still in love with each other. Watch this movie if you're looking to rekindle a long lost relationship or reignite some romance.

Audrey Hepburn and George Peppard in Breakfast at Tiffany's (1961) - What made Tiffany's so magical was that this unlikely pair of dreamers didn't need fame or fortune to be happy. All they needed was each other, a cat and "Moon River" playing to make movie magic.

Julia Roberts and Richard Gere in Pretty Woman (1990) - The story might have resembled a modern day Pygmalion, but the genuine affection between Gere and Roberts made it worth watching. Woman was the film that truly introduced Julia Roberts to the masses. She made it possible and believable to root for an LA hooker looking for Mr. Right just like the rest of the world. Gere and Roberts attempted to repeat their movie success in 1999's Runaway Bride with mixed results. Hopefully, their next film will have better luck.


Renee Zellweger and Colin Firth in Bridget Jones's Diary (2001) - Before Firth received awards show raves for The King's Speech, he was best known as Mr. Darcy in both Pride and Prejudice and this film. He made women swoon in both as a reserved man with a heart of gold as he embraced an unexpected love interest. Firth's chemistry with Zellweger might've been underplayed as her relationship with an arrogant playboy (Hugh Grant) that dominated most of the film, but it was their quiet interaction that made audiences cheer.


Kathleen Turner and Michael Douglas in The War of the Roses (1989) - Okay, this entry might not be a typical romantic comedy like Romancing the Stone, but there was still a romance to the movie couple's hatred for each other. Most movies followed an unlikely couple inching closer together and concluded with them walking off into the sunset together. In the case of Roses, Douglas and Turner met cute, got married rather quickly and launched a bitter divorce war. This might seem like a strange movie to watch on Valentine's Day. Douglas and Turner spent more of the film fighting than loving each other, but the film's message made up for it in the end. Roses warned audiences to fight for their relationships instead of throwing in the towel at the first sign of trouble.

Movie Misses

Jennifer Aniston and Kevin Costner in Rumor Has It (2005) - A romantic comedy that should've been scrapped instead of made. An embarassment to all involved. It was a chronically unfunny film with a plot straight out of a blender. Not even the all-star cast could save this film from itself. The film's most uncomfortable pairing was the commitment shy Aniston and Costner's playboy who slept with both her mother and grandmother. She was initially disgusted with the idea, until she too fell victim to Costner's charms. Sadly, the audience remained uncomfortable for the duration of the movie.


Bruce Willis and Kim Basinger in Blind Date (1987) - In the 1980s, Willis was defined as a charming cut-up onscreen through TV's Moonlighting. Unfortunately, his charm couldn't save him, or the audience, from a nightmarish blind date. The first half of the film started to work as Basinger and Willis spent their date running from one crazy scenario to the next. Once the date was over, the film should've been too. The movie went wrong when the mismatched Willis and Basinger magically fell in love after that one date. They should've ran, like most moviegoers, in the opposite direction instead of to each other.


Reese Witherspoon and Paul Rudd in How Do You Know (2010) - Director James L. Brooks struck move gold in the 1980s with Broadcast News and Terms of Endearment. It seemed like this film would be added to that list. Unfortunately, that wasn't the case. Witherspoon and Rudd's characters weren't properly developed into realistic individuals. The audience didn't know whether to root for them or leave the theatre instead. The latter is definitely recommended.


Julia Roberts and Nick Nolte in I Love Trouble (1994) - Trouble was an accurate term to describe this dreadful movie where Roberts and Nolte tried to be a more current His Girl Friday as rival reporters in search of a story. What the audience received was a cookie cutter storyline and two stars who clearly didn't like each other. If the actors couldn't fake their onscreen relationship, moviegoers shouldn't pay to see it.

Jennifer Lopez and Ben Affleck in Gigli (2003) - Many movie insiders believed that Lopez and Affleck's offscreen love match would translate well onscreen, which was further from the truth. The stars looked like they would rather be at the Dentist's office than in this ridiculously unfunny film. It appeared their only motivation to do Gigli was for a large paycheck and not the stereotype heavy script. Avoid this film at all costs, unless you're looking to cure insomnia.

Ultimately, it is uncertain what makes certain romantic comedies succeed or become a flop. An all-star cast doesn't necessarily guarantee box office gold or critical acclaim for that matter. (Valentine's Day might be the exception to the rule, because it was released around the actual day.) Nowadays, Hollywood is trying to crown the next Julia Roberts or Meg Ryan with little luck. The true success stories are movie couples that people can root for, instead of substandard films that have been done before with better results. If you're looking to see a new movie with your sweetheart, see Adam Sandler's latest Just Go With It. Hopefully, this film will be going in costar Jennifer Aniston's win column and not follow suit like Rumor Has It.

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    • Cogerson profile image

      UltimateMovieRankings 

      7 years ago from Virginia

      Awesome hub....you did a great job researching all those movies...very impressive....I think you could add Woody Allen and every actress that has played his love interest in his last 10 movies he acted in....thanks for the information

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