Director Nicholas Ray saw no problem mixing business with pleasure. After all, he had two affairs while making his iconic film Rebel Without a Cause. While James Dean was not one of his conquests, the two did share an intense bond that went beyond an intimate affair. And when Dean tragically lost his life, a wounded Ray descended into a chaotic, debauched lifestyle that seemed to be chasing one thing: the elusive youthful rebel that was James Dean.

Many believe that the oddly-named artist Captain Beefheart was the father of punk and new wave music. But it was behind the scenes where Beefheart became a true visionary. Unfortunately, it came at the expense of his bandmates.

After discovering his true passion, Bob Ross made possibly the biggest career change imaginable to gamble on a job in television, and the TV world was all the better for it. Not knowing just how iconic he would become, Bob’s only goal in life was to make the world a better place by teaching people art, something he was lucky enough to do until the end of his days—but that was when the trouble began.