Gordon Gekko

Michael Douglas won the Academy Award for Best Actor playing Gordon Gekko, and then something unexpected happened: Gekko, the villain of Oliver Stone's anti-corporate morality tale, became an aspirational figure. Wall Street traders adopted his mannerisms, his slicked-back hair, and his philosophy. 'Greed, for lack of a better word, is good' was supposed to be an indictment. Instead, it became a motto. The disconnect between Stone's intention and the audience's reception is one of the most fascinating cultural phenomena in cinema.

Douglas plays Gekko with a predatory charisma that makes his villainy seductive. Gekko is not a thug or a maniac. He is the smartest person in every room, he sees opportunities that others miss, and he has the courage to act on them. His monologue to the stockholders of Teldar Paper — the 'greed is good' speech — is a masterclass in persuasion: it is logical, it is passionate, and it is deeply, fundamentally wrong. But in the moment, delivered with Douglas' electric conviction, it sounds right. That is what makes Gekko dangerous.

Gekko predicted the financial culture that would produce the 2008 crisis two decades later. His philosophy — that corporate raiders create value by stripping assets and that greed drives economic progress — became the operating system of Wall Street in the 1990s and 2000s. Stone created a cautionary tale. The people he was cautioning took notes.