Indecent Proposal (1993) paired him with Robert Redford and Demi Moore in a high-concept drama about a wealthy man who offers a million dollars to sleep with a married woman. Harrelson played the husband — the man who agrees to the arrangement and then has to live with what it does to his marriage. The role placed him in the specific emotional territory of masculine uncertainty and shame that would become a recurring strand of his film work.
Natural Born Killers (1994) was the defining film of his early film career — the one that most completely demonstrated what he was capable of when the material was genuinely ambitious. Oliver Stone’s deliberately stylized portrait of media-created celebrity killers starred Harrelson as Mickey Knox, alongside Juliette Lewis as his partner Mallory. The film is a provocation: noisy, formally inventive, politically engaged, and deeply uncomfortable. Harrelson’s performance is the film’s center of gravity, a portrayal of charismatic violence that managed to be simultaneously repellent and compelling — which was exactly what the film required.
The personal resonance of playing a murderer who achieves celebrity, for a man whose father was a convicted murderer of considerable public notoriety, is available to be noted. Harrelson has not drawn this parallel publicly in any sustained way, and speculating about the unconscious connections between an actor’s biography and his professional choices falls quickly into the territory of amateur psychological diagnosis that the prompt for this article explicitly warns against. What can be noted is simply that he made the choice — that playing Mickey Knox was a professional decision he made, and that the decision was consistent with a pattern of choosing characters who exist at the moral margins.