When Jack Met Marilyn

5 JFK Dumps Sinatra March 23, 1962
Frank Sinatra liked Jack Kennedy, calling him ''Chicky Baby'' and introducing him to socialite Judith Campbell, who became the president's mistress. Sinatra also set Campbell up with mobster Sam Giancana, who allegedly gave Sinatra cash to help JFK in the primaries. But postelection, the Rat Pack got the cold shoulder from the White House. First, Sammy Davis Jr. was frozen out of the inauguration festivities after marrying white actress May Britt. Then Sinatra, planning to host Kennedy in Palm Springs, built a helipad and made other costly renovations to render his home suitably presidential. But when Bobby Kennedy found out that Sinatra had also hosted Giancana, JFK decided to stay with Bing Crosby instead. Sinatra is said to have smashed the helipad with a sledgehammer.

4 Rock Hudson Opens Reagan's Eyes May 15, 1984
At a White House dinner, Nancy Reagan noticed that Rock Hudson had lost weight. ''I caught some flu bug when I was filming in Israel,'' explained the lifelong Republican. But he had AIDS. In July 1985, amid rumors about the cause of his illness, Hudson sought treatment in Paris. There he received a sympathetic phone call from President Reagan, who also asked his own doctor, John Hutton, about AIDS -- the first time on record that Reagan expressed curiosity about the epidemic. But the information made little impact on the president. ''He accepted it like it was measles and it would go away,'' Hutton said. Hudson died that October 2.

3 Bubba Plays Sax for Arsenio June 3, 1992
''We had just won the California primary, but we trailed President Bush and Ross Perot in the polls,'' recalls ''Crossfire'''s Paul Begala, then one of Bill Clinton's campaign managers. ''We had to do something. Hillary remembered the good programs Arsenio Hall had put on during the L.A. riots, and suggested that we go there.'' The question wasn't if he should appear on the show or even if he should play the sax, but should he wear shades? ''The governor asked James Carville, who said, 'Guhv'nuh, Ah'm pre-Beatles and Paul is post-Beatles, and this is definitely a post-Beatles decision,''' Begala explains. ''So I gave him my sunglasses.'' The appearance showed Clinton as loose and likable and well versed on the issues, which boosted his popularity over the next six weeks, pushing him into the lead and on to the presidency.

2 The King Goes Souvenir Hunting December 21, 1970
Royal visits usually require planning, but at 8:45 a.m. Elvis Presley pulled up to the White House with a note requesting a meeting with President Nixon. The note said Presley (who happened to be stoned at the time) wanted to fight drug use, be named a federal agent at large, and be given ''credentials.'' Excited White House aides secured approval, and at 12:30 Presley entered the Oval Office, sans gift -- an automatic pistol, which had been confiscated by the Secret Service. When Presley got what he was really after -- a narcotics bureau badge for his collection of police paraphernalia -- he hugged Nixon, acting more like a thrilled tourist than the King.

1 An Icon Wishes an Icon Happy Birthday May 19, 1962
John F. Kennedy celebrated his 45th birthday 10 days early, at a fund-raiser in New York's Madison Square Garden that featured Jack Benny, Harry Belafonte, Henry Fonda, Nichols and May, and, immortally, Marilyn Monroe. And to think she almost didn't make it: Twentieth Century Fox refused to give her two days off from shooting her final film, ''Something's Got to Give,'' even when Bobby Kennedy intervened. But the world's most famous sex symbol went AWOL, determined to achieve her masterpiece. Monroe hired designer Jean Louis to make a flesh-toned gown of silk soufflé gauze studded with rhinestones and sequins, with such a snug fit that it had to be sewn onto her the night of the performance. She took the stage in a white fur wrap, which she dropped upon reaching the microphone, revealing herself in all her shimmering opulence. The crowd whooped, Kennedy clenched a cigar, and Monroe, running her hands along her body, delivered a breathy version of ''Happy Birthday'' that aired on network newscasts. She was ''making love to the president in the direct view of 40 million Americans,'' wrote one columnist. JFK didn't seem to mind. ''If I ever saw an appreciation of feminine beauty in the eyes of a man,'' said Time's Hugh Sidey to biographer Seymour Hersh, ''it was in John F. Kennedy's eyes at that moment.'' Kennedy's comment: ''I can now retire from politics after having had 'Happy Birthday' sung to me in such a sweet, wholesome way.''