"How about Woody Allen AND Billy Crystal as love interests for Elizabeth Shue in Deconstructing Harry? The sight of both of these (nearly) 60-plus men pawing the luscious Shue had me gagging on my popcorn."
"Woody Allen and Helen Hunt in Curse of the Jade Scorpion. It was just creepy to watch the both of them."
"I'd be hard pressed to find a worse pairing than an especially wilted and aged Woody Allen as the once and again love interest to the insanely sexy and youthful Tea Leoni in Hollywood Ending. The idea (and then image) of the two swapping spit was both nauseating and ridiculous. And I'm a big Woody Allen fan."
It's odd that no one mentioned the Woodman and his partner in the documentary Wild Man Blues: Soon-Yi Previn. But maybe that's a case of surprisingly alchemy: She doesn't seem all that wrong for him. Certain overmothered Jewish men need women who are alternately worshipful and ball-busting, and Soon-Yi, with her lithe body and sensuous mouth and bossy attentiveness, clearly fills the bill.
One more thing before we get off Allen's case. Back when he had a sense of humor, he made that disconnect with attractive women a source of laughs (and intentional squirms). But by his later movies, his celebrity had fogged his brain. He just acted entitled.
Before sampling more reader responses, I want to mention another stunningly inapposite pairing: Dustin Hoffman as the son of Sean Connery in the 1989 clunker Family Business. You think: Who was the mother? Dr. Ruth? Adding to the surrealism: Matthew Broderick (a wiseass showbiz kid resembling neither of his co-stars) as Hoffman's son. What made this even worse than it sounds (if that's possible) is that the film was about genetic ties that you can't transcend. Which is, come to think of it, exactly right.
Sylvester Stallone got some votes: Because of his titanic insecurity and its compensatory narcissism, he looks wrong with just about everyone. "mdw" cites Stallone and Martin Scorsese as hoodlums in Paul Bartel's 1976 Cannonball. ("Watch their scenes together—even more awkward than you might imagine.") Will Pfeifer mentions Stallone and Sandra Bullock in Demolition Man (also featuring Andre Gregory and Jesse Ventura!). It's a hard choice, but my vote for the worst Stallone pairing: with Dolly Parton in the H-bomb Rhinestone. It didn't work to cast Stallone as a grossly obnoxious idiot because he thought he had to, um, act.
Speaking of Dolly, from Keith Thompson: "Acting talent is not the issue with Dolly Parton and James Woods in Straight Talk. Woods has a marvelous knack for both comedy and drama, and Dolly Parton commands a crowd-friendly, folksy charm that suits her in many entertainment mediums. It's just the Tabasco-and-Haagen-Dazs pairing of the two of them that's so bloody jarring."
I like Woods, but he's so edgy and full of himself that he rarely connects with anyone. The exception, creepily enough, was as the ex- of Sharon Stone in Casino. They were strikingly plausible as a couple you'd ask to be moved away from in a restaurant.
Many of you wrote with examples of miscasting, which is a different issue (although I did like Kathleen Boergers' "Keanu Reeves interacting with Shakespearean dialogue in Much Ado About Nothing"). The fun thing about this contest is that it makes you think about that elusive quality, "chemistry," and why some movies play like failed science experiments.
Herewith, more of your favorite mismatches: