38. James Dean (Life insurance) - $100,000

James Dean is such an icon that people forget that he wasn't a star for that long before he passed away. They say the brightest stars burn out the fastest, and his star was certainly bright. He was the bad boy heart throb that America needed. Now the closest thing we have to James Dean is James Franco. It doesn't feel like an even trade, does it?

I think James Dean knew something that we all didn't, because he took out a life insurance policy, and then some time later he crashed his Porsche and died. It's a chicken or the egg type of situation. Did he get the life insurance because he drove recklessly, or did he drive recklessly because he got the health insurance? There's only one way to know. We go to Heaven and ask him ourselves!

NEXT


Copyright © 2026 CultureHook