Zsa Zsa Gabor + Pamala Stanley: The Hungarian road pest and the HiNRG "Coming Out of Hiding" singer seem to have crossed paths during the '80s and paused to feed the flash.

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Gary Coleman + Mark Messier: The pint-sized Diff'rent Strokes star was passing through Edmonton and came by to say hello to the team when a beer-chugging, barely-dressed Messier—who went on to become a hockey legend—posed for this legendarily odd photo op.

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Rue McLanahan + Dustin Hoffman: What a hot piece Dusty was! This snap was taken backstage at Jimmy Shine (McClanahan's Broadway debut) when she was 35 and he was 32, yet they look like mother and son due to the wardrobe/lack of wardrobe. McClanahan had the good sense to include this one in her book My First Five Husbands...And the Ones That Got Away (2007).

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More after the jump...

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Woody Allen + Ginger Rogers: The neurotic Manhattanite and the arch-conservative Hollywood grande dame came together when testifying before Congress against colorizing black-and-white films.

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Mae West + Wayland Flowers: Maybe it should read "Mae West + Madame!" The cartoonish superstar was around 80 when she shared air with the most famous, campiest puppet of the '70s and the dude who fisted her every day.

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Carol Channing + Supreme Court Chief Justice John Roberts: At George Washington University in 2006, Roberts was presiding over a competition and Channing was singing in honor of the school's 185th birthday when they ran into each other. Roberts had anticipated the encounter, bringing a vintage photo of Channing for her to sign. Wait, didn't he adopt his kids?

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Elvis Presley + Fred Astaire: Yes, this one has an Old Blue Eyes bonus. The King of Rock 'n' Roll and the Emperor of the Dance Floor pointing at each other look like they're accusing each other of mischief or are acting out the passage of pop cultural time.

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Jane Fonda + The Village People: I wonder if Jane was torn between finding this group a hoot or worrying that she was posing with a cynical capitalist endeavor (which is what she reportedly felt about The Exorcist, a movie she haughtily turned down).

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Sam Trammell + Jane Withers: I shot this one myself! True Blood hottie Trammell and one-time child star Withers met up at a recent autograph show in Burbank. He was definitely more excited to be presented with Withers than he was to be presented with the unflattering shirtless photo I brought for him to sign.

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Mamie van Doren + Gloria Allred: The ambulance-chasing feminist attorney and one of the 20th Century's (heck, she looks pretty good in the 21st, too!) biggest sex symbols came together in the Batmobile at an event honoring George Barris's lifetime achievements.

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John McEnroe + Meat Loaf: The bad boy of tennis and the guy who uses a dashboard as his primary light source look like they should not have been left unsupervised.

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First Lady Rosalynn Carter + John Wayne Gacy: One of the creepiest photo ops ever is this palm-crossing between President Jimmy Carter's wife and one of the worst, most diabolical mass murderers in history. Gacy had ingratiated himself into the Chicago Democratic Party even while he was luring teenage boys to their deaths. Morbid multi-tasker.

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Mikhail Gorbachev + Lucy Liu: This unlikely pair met up at the 2006 Women's World Awards. As cool as this photo is, a version also exists with Pakistan's martyred Benazir Bhutto.

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Huey Lewis + Madonna: Sure, they're both singers, but what a quirky duo they made even back in 1985, when they got together to present a trophy at the American Music Awards. The Square and the Queen of Cool. Neat!

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Matt Dillon + Tony Sirico: Flamboyant "Paulie" from The Sopranos crossed paths with '70s/'80s heartthrob Dillon at an NYC event. No real connection, and yet they look like they called each other before dressing!

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Jaleel White + Charlie Sheen: Something about seeing "Urkel" mixing it up with The Notorious S.H.E.E.N. really makes me uncomfortable. And sure enough, White really did wind up being as terrible an influence on Charlie as I'd feared.

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Pat Boone + Dave Grohl: The meanest thing my mom ever said about my dad—and they're divorced—is that he liked Pat Boone when they were teenagers. Here, the uncoolest singer alive (for now) makes like a rockstar with Nirvana/Foo Fighters member Grohl.

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Hugh Jackman + Rupert Murdoch: Australia's "Mr. Burns" is cozier with the man who brought Peter Allen alive on Broadway than you might think. In fact, Jackman is the godfather of one of Murdoch's young children. (Nicole Kidman is the godmother.) I realize the dude is more powerful than polonium, but I'd avoid him like I avoid polonium, too. I guess being Australian, getting asked to be a godparent to his kid is an offer Hugh can't refuse.

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Xuxa + Michael Jackson: The Brazilian children's TV show host/recording artist meeting up with the King of Pop was like pouring sugar on a hot fudge sundae. This looks more like something Jeff Koons would paint that an actual occurrence that was photographed.