Marilyn Monroe
Such is the wattage of both Monroe and John F. Kennedy that rumors of their affair have kept tongues wagging more than 40 years later. Though there has never been official confirmation of any of Kennedy's dalliances, there are indications he was unwilling to cede his playboy lifestyle to the conventions of marriage. Of his supposed conquests, Monroe tops the list. A sultry version of "Happy Birthday" sung by Monroe to Kennedy at Madison Square Garden in 1962 was supposedly the impetus for their affair:
Post-affair: Monroe died later in 1962 of a drug overdose, but tales about her alleged fling with the President grew increasingly tall. FBI Director J. Edgar Hoover tried to prove that the man on a secret FBI sex tape of Monroe was Kennedy, but he lacked definitive proof. Others claim Kennedy was involved in her death. Needless to say, the rumors are even less substantiated than the affair itself.