Winona Ryder And … Richard Gere? Movie Couples Gone Horribly Wrong

Sometimes onscreen pairings leave audiences for romance flicks feeling cold.

Love means never having to say you’re sorry. With another Valentine’s Day upon us, however, we can’t help but think back to the catastrophic couples whose clunky, robotic, unlikely romances left us demanding an apology — and our 10 bucks back. Like a scorned lover, then, we’d like to take a moment around this February 14 to throw a symbolic glass of water in the collective face of movie couples whose supposed unions made us want to object. If we never see them onscreen again making goo-goo eyes at each other, it’ll still be too soon:

(See photos of some of the big screen’s most poorly matched couples right here. )

Sean Connery and Catherine Zeta-Jones (1999′s “Entrapment”)

Ever since we first laid eyes on Catherine Zeta-Jones we had the vision — there she was, scantily clad, emerging from the surf à la Ursula Andrews. Fiery, spirited and gorgeous, she would make the ultimate girl for James Bond.

But, c’mon, not like this.

To be fair, the couple’s age difference (he was 69, she was 29) was addressed in the film, but 40 years is too much to ignore. Hell, we’re still trying to figure out her marriage to Michael Douglas, and he’s just a measly 25 years older. Thankfully, this self-contained film is unlikely to inspire a sequel.

Hayden Christensen and Natalie Portman (2002′s “Star Wars: Episode II — Attack of the Clones” and 2005′s “Star Wars: Episode III — Revenge of the Sith”)

Lay the blame wherever you like for the artistic failures of the “Star Wars” prequel trilogy (and Lord knows there’s plenty to go around), but make sure to save a heaping handful for these two typically fine actors who, with stilted deliveries and mannequin-esque expressions, reduced the greatest villain in cinema history to a spazzy kid in love with an insecure whiner.

If someone someday compiles a list of the worst movie moments of this decade, a spot would undoubtedly be held for the cringe-inducing scene in which Anakin and Amidala frolic in a CGI field with a comic-relief wooly mammoth-like beast. Honestly, there was more chemistry between Han Solo and his 7-foot-tall walking carpet.

Both Christensen and Portman are fantastic actors. Both will have long and productive careers. And both should stay as far away from each other as possible.

Woody Allen and … Julia Roberts, Elizabeth Berkley, Elisabeth Shue, Mira Sorvino, Charlize Theron, Helen Hunt, Téa Leoni, etc.

When the Woodman married Soon-Yi Previn in 1997, some were shocked that he’d become involved with a woman nearly 35 years younger. Others simply pointed to “Manhattan,” “Husbands and Wives,” “Stardust Memories” and so many other films in which Allen contemplated the temptations of younger women.

Much of Allen’s genius over the last decade and a half was ultimately undermined, however, as he cast himself opposite the hottest young flavors of the month, each eager to work with a legend. Things became particularly absurd when the 2001 bomb “The Curse of the Jade Scorpion” had a tired, 66-year-old Woody being pursued by Theron, “Showgirls” star Berkley and Hunt, who seemed a far more reasonable match since she was only three decades younger.

Thankfully, Allen came to his senses in enough time to spare us love scenes with recent muses Christina Ricci and Scarlett Johansson. Rumor has it that Penelope Cruz will star in Allen’s next project. Here’s hoping she’s not playing his girlfriend.

Eddie Murphy and Eddie Murphy (2007′s “Norbit”)

In all likelihood, Eddie Murphy will start being known as “Oscar-winner” Eddie Murphy by the end of the month. And, as we saw with this week’s #1 opening of his latest movie, Murphy’s comedic strengths remain equally as potent. The man has been blessed with an uncanny knack for creating multiple characters out of thin air, often in the same movie. But that doesn’t mean we want to see two of them getting it on.

We’re looking at you, “Norbit.”

We find the very idea of Murphy-on-Murphy action a bit too creepy. Self-love should be reserved for acceptance speeches, Eddie, and we’re pretty sure you’ll be getting your chance real soon.

Julia Roberts and Nick Nolte (1994′s “I Love Trouble”)

Seriously? We’re supposed to believe that sweet, wide-grinning, endlessly wholesome sweetheart Julia Roberts would somehow end up with the cranky, odd-looking man who would someday yield the greatest mug shot of all time?

Rumor has it that Nolte and Roberts despised each other on the set of their romantic-comedy clunker, and the results sure showed. But the most amazing thing about such onscreen pairings is that dozens of studio executives, agents, producers and other handlers all must sign off on a project before it can be made — in this case, clearly ignoring a lack of compatibility immediately obvious to anyone in the real world.

Hilary Duff and Chad Michael Murray (2004′s “A Cinderella Story”)

They’re both young, they’re both cute and they both have loyal fanbases. So why did Hilary have such a hard time convincing Murray that he can’t get enough of that wonderful Duff?

Maybe it was because the fresh-out-of-”Lizzie McGuire” star looked even younger than her 16 years in the movie, or perhaps it was because her leading man was pushing 23. Then again, any actress hoping to compete with CM-squared’s affection for himself would seem to be fighting a losing battle.

Whatever the reason, “Cinderella” ended up becoming a fractured fairy tale, and that poster shot of a gown-wearing Duff on Murray’s shoulders left audiences with an expression as pained as the James Dean wince on Murray’s face.

Sarah Jessica Parker and Matthew McConaughey (2006′s “Failure to Launch”)

Much like the Yankees teams of the last six years, this seemingly formidable lineup looked a lot better on paper than in reality. McConaughey had curly blond hair, a natural charm and a string of romantic-comedy hits, while his leading lady boasted the most popular romantic TV show in recent history, and equally powerful charisma and curls. It should have been a clash of the titans, right?

Well, something funny happened on the way to the bank: The two stars seemed as uninspired as the script, and audiences soon realized that “smug” is not a character trait any couple should share.

There’s no doubt both will resurface again in other romantic comedies (in fact, they already are — McConaughey is currently filming opposite Kate Hudson in “Fool’s Gold” and Parker is making “Smart People” with Dennis Quaid), but this “Failure” might go down in history as one time when the Hollywood formula just didn’t compute.

Winona Ryder and Richard Gere (2000′s “Autumn in New York”)

You can be excused for saying “Wait a minute — these two made a romantic movie together?” since virtually no one saw it. But believe it or not, someone once thought that a baby-faced actress, a gray-haired-forever actor and the 22 years between them would make for a blockbuster.

Needless to say, it didn’t. While attempting to be the “Love Story” for a new generation, “Autumn” cast Ryder as a terminally ill young woman finding love in Gere’s squinty eyes and self-satisfied grin. Unfortunately, Ryder’s demise carried about as much emotional resonance as the death of a background character in a zombie movie.

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