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When Jack Met Marilyn

Bizarre encounters between presidents and entertainers. EW counts down the 20 most memorable political milestones in the last 61 years

Nancy Reagan, Ronald Reagan, ... | NO. 18: JACKSON WITH THE REAGANS
Image credit: The Reagans and Jackson: Photofest
NO. 18: JACKSON WITH THE REAGANS

If Washington, D.C., isn't the most political town in America, then Hollywood is: The Weinsteins' machinations put most political operatives to shame. And if Hollywood isn't the most showbizzy town, then Washington is: It takes consummate actors to utter lines like ''I'm not a crook.'' Sometimes, the worlds actually collide. The meeting between Abe Lincoln and John Wilkes Booth may have been less than auspicious, but more recent encounters have proven to be, if not cultural milestones, then at least moments of odd illumination.

20 Sammy Embraces Tricky Dick August 23, 1972
Though stiffed by Kennedy, Sammy Davis Jr. was wooed by Nixon, who requested that Davis sing ''Candy Man'' at the GOP convention. Later, when Richard Nixon thanked Davis, the crooner grasped him in what was -- until Monica greeted Bill on the rope line -- perhaps the sincerest, most exuberant hug that anyone ever gave a president in public.

19 The Big Rubdown October 5, 1965
Scene: night at the White House. Lady Bird Johnson, just out of the pool, towels off. She walks into the bedroom, where she finds her husband, naked, getting a massage and talking about Vietnam, as Gregory Peck, Hugh ''Wyatt Earp'' O'Brian, and Hubert Humphrey, along with several aides, look on. ''I shrieked and backed out,'' Mrs. Johnson wrote in her diary. ''What a household! And what a moral to always have your hair combed...''

18 The Gipper Welcomes the Gloved One May 14, 1984
When the Transportation Department wanted to use ''Beat It'' in an anti-drunk-driving ad, Jackson wheedled a White House invitation in return. ''Well, isn't this a thriller,'' quipped President Reagan, before awarding Jackson -- who was decked out in a sequined dress uniform and sunglasses -- a plaque for his efforts. But afterward, when Jackson thought there were too many people at the reception, he locked himself in a bathroom until they went away.

17 Gerry Flirts With Zsa Zsa March 17, 1976
Who knew that Gerald Ford could be so playful? In her 1991 memoir, Zsa Zsa Gabor wrote that while she was dancing with him at a White House dinner, Ford whispered, ''If I weren't married, the two women I'd want to go to bed with are you and Ann-Margret.'' Gabor wondered if Ford was just flattering her, ''although by including Ann-Margret, he didn't really display a dazzling grasp of diplomacy.''

16 Bob Hope Meets His First President February 12, 1943
After endearing himself to GIs by venturing deep into combat zones to entertain the troops, Bob Hope won over their commander in chief, FDR, at the White House Correspondents' dinner, with gibes about Republicans, the vice president, and FDR's peripatetic wife. ''I heard you just had a conference with Winston Churchill...about war strategy,'' Hope joked, ''meaning where will we attack the enemy and how are we going to keep Eleanor out of the crossfire.'' Roosevelt roared. ''He was the best audience,'' said Hope.

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