Look, we’ve all had that one wildcard friend from college who you can’t really bring around the spouse and kids because you know they’re still going to bring that craziness to the quaint dinner function. You’ve grown up a little. Maybe you’re a well-respected individual now. Maybe you’re even a distinguished member of the community. So, sadly, you’re gonna have to leave crazy Dave in the past.

Whether you regret those nutty college pals, or remember them fondly, you might want to scroll way back on Facebook and start deleting those pics. Because your current, mature, level-headed friends are definitely going to think, “Wow, I can’t believe you hung out with that lunatic.” These prominent folks are no different. Well, except that some of their old pals were Charles Manson, Saddam Hussein, and Hitler. Yeesh. So here are 15 beloved figures with ties to some of the shadiest, most evil people in history.

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