5. Marilyn Monroe and the Kennedys
She struggled with drug and alcohol abuse for most of her career, as well as chronic lateness and unprofessional behavior that made many directors refuse to work with her.
Many have speculated she might have suffered from bipolar disorder and depression as well.
All of this unstable behavior, coupled with her immense beauty, made for some extremely sordid affairs with some extremely powerful people.
She was married to Pulitzer Prize winner Arthur Miller and baseball Hall of Famer Joe DiMaggio, but her most infamous liaisons were with the Kennedy brothers, John and Robert.
The Kennedy family has never confirmed the affairs took place, but it’s been widely speculated for nearly half a century that John and Robert Kennedy were both infatuated with Monroe. Her famously seductive rendition of “Happy Birthday, Mr. President” at the President’s 45th birthday only fueled the flames of speculation.
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Hollywood private eye Fred Otash even claimed he had FBI wiretap recordings of the pair having sex. Whatever the truth, both were powerful people and known to be promiscuous, and their untimely deaths will likely keep conspiracy theorists guessing for years to come.