1. "Red River" (1948): Wayne portrayed Thomas Dunson, a headstrong and ruthless cattle rancher who leads his crew on a perilous cattle drive. While he is not an outlaw, Dunson's methods are often questionable, and he conflicts with his foster son regarding leadership and morality.
2. "The Searchers" (1956): Wayne played Ethan Edwards, a Civil War veteran who embarks on a relentless pursuit to rescue his niece from Native American captors. While Edwards's determination and courage are admirable, his obsessive quest and questionable actions make him a complex and morally conflicted character.
3. "The Shootist" (1976): In one of Wayne's final roles, he portrayed John Bernard Books, an aging gunfighter who returns to his hometown to confront his mortality. Books is a tragic figure, haunted by his past and facing his impending demise. While not a traditional outlaw, Books represents a dying breed and the consequences of a violent life.
These instances demonstrate that while John Wayne primarily portrayed heroic characters, he also ventured into morally complex roles that showcased his versatility as an actor.