1. Jordan Belfort in The Wolf of Wall Street

No Scorsese criminal has been simultaneously as irresistibly charismatic and as undeniably problematic as degenerate playboy and Wall Street trader Jordan Belfort in The Wolf of Wall Street. Besides casting Leonardo DiCaprio, one of the most charismatic movie stars of all time, to play Belfort, Scorsese seems dead set on making his criminal exploits as reprehensible and thrilling as possible. We all know driving under the influence is reckless and can kill innocent people. That didn’t stop any of us from nearly projectile vomiting from laughter watching Belfort crawl to his car to drive home under the influence of 15-year-old Quaaludes. There’s Belfort’s famous “I’m not leaving” speech that could hype up a corpse, Belfort casually explaining how his firm committed market manipulation through backdoor IPO deals, and of course, there’s Belfort’s sales psychology lesson on display in getting someone to sell him a pen.

Eventually, the same arrogance and charisma that Scorsese inundates us with is what begets Belfort’s fall. His feeling of being untouchable leads him to disregard FBI investigations which leads to him taking incriminating phone calls which leads to his arrest. He nearly dies when his yacht capsizes after he wanted to ride in a storm in order to smuggle money out of Switzerland. The man who was worshipped as a god by employees like Donnie Azoff (Jonah Hill) eventually turned on those people to save himself. In the end, Scorsese paints a cautionary tale of how charisma and criminality only mix for so long before the former makes the latter a kind of death sentence.