Anjelica Huston is truly Hollywood royalty. Born into one of the most prestigious families in cinema history, Huston's life is full of immense privilege, heartbreaking tragedy, and lasting scandal. Huston may be on top now—but it was one heck of a twisted journey for her to get there.

Lee Marvin turned a film career of playing heavies on horseback into an eventual Best Actor Oscar win. And he seemed to do it one bottle at a time.

Lou Reed is one of the most influential musicians of all time. Known for his transgressive lyrics and experimental songwriting, Reed’s artistic reputation propped up a life of darkness, debauchery, and depression.

No matter how many try to take the mantle, Marilyn Monroe remains the ultimate classic Hollywood story, equal parts glamorous and tragic. Born Norma Jeane Mortenson in 1926, she had a heartbreaking childhood before bursting into the world of pin-up modelling and eventually, Hollywood. Although she only acted for about a decade, Monroe became incredibly famous—only to suddenly pass at just 36 years old.

Dennis Hopper didn’t just play a counterculture rebel in the iconic 1960s flick Easy Rider—he lived a shockingly rough and risky life.

Sophie Tucker was a legendary entertainer who left audiences tickled and titillated. Sadly, she was the last of her kind and led a secretly lonely life.