1. Marilyn Monroe
Cheater: President John F. Kennedy
Date Of Affair: 3/24/1962
Nearly half a century after her death, Hollywood legend Marilyn Monroe remains one of the world's most recognized sex symbols. The pin-up model and actress is also famous for being The Other Woman. Yet this was no typical Tinseltown fling. Her alleged relationship was with none other than President of the United States John F. Kennedy. Even today, however, getting to the truth of what actually happened has been sketchy at best (declassified FBI files are heavily censored). But, supposedly the story is that in February 1962, the President's sister introduced her brother to Marilyn at a dinner party.
A notorious ladies man, Kennedy invited Monroe to meet him in Palm Springs, California on March 24 where they engaged in hanky panky-apparently, the only time they did the deed. (Rumors abound that Monroe simultaneously carried on an affair with JFK's brother Attorney General Robert Kennedy, too.) The always classy First Lady Jackie Kennedy allegedly knew about the fling but let things slide until the obsessed Marilyn famously flirted with JFK as she sung "Happy Birthday" to him during a televised Madison Square Garden concert in May. Her threats of divorce would have derailed the President's chances of re-election, so he cut off all contact with the star.
Three months later, Marilyn Monroe, severely depressed (she had a history of suicide attempts and problems with pills and alcohol), died of an apparent overdose on August 5, 1962, causing conspiracy nuts to wonder if the blonde bombshell had been assassinated to avoid a political scandal of epic proportions.