The problematic John Wayne became a fierce force in American cinema as the designated leading man in a series of big budget films. In an era full of trauma and sadness, Wayne as an American symbol, represents a significant contribution to the world during the time of uncertainty and panic.

As his career elevated in the midst of WWII, he rose through the ranks as the single most popular actor in Hollywood’s history. The reason that Wayne had become increasingly famous was associated with his no-nonsense characters that male viewers related to and women gravitated towards prior to the cultural changes of the 1960s. He brought to light this persona of elevated masculinity that was culturally striking to watch. From Academy Awards to a rich career that very few have been able to achieve, the praise associated with his on-screen portrayals will live on through generations.

In a successful career spanning over 50 years and 169 movies, Wayne has had his highs, in addition to his fair share of criticism, which is ultimately impossible to ignore. During a 1971 Playboy Magazine interview, Wayne made comments speaking negatively against the African-American community and making a series of homophobic slurs, while directly addressing his belief in white supremacy. Some have marked this up to be a time sensitive issue, with societal problems and norms being completely different from what it is now (or is it?). The truth is, this stuff was said, and it hasn’t gone over well since the interview resurfaced, with John Wayne’s legacy denounced by many.

Taking a moment to separate the man from his artistry is quite a difficult task, and directly addressing the controversies of his past comments creates difficult decisions that can often lead to either supporting art and ignoring prejudice, or completely erasing history. What people can all agree on is that his work ultimately changed the scope of Hollywood cinema, and how masculinity and machismo are portrayed through verbal and physical modes of storytelling. Thus, instead of calling these films his ‘best performances,’ perhaps we should consider these movies to have the most macho roles from John Wayne, a problematic actor who presents culture with a fascinating way to dissect American masculinity.

6 The Barbarian and the Geisha

The Barbarian and the Geisha is based on the true story of Townsend Harris, an American diplomat who was sent to the country of Japan in order to serve as a U.S. consul member. Wayne plays Harris as he is met by residents in the small village of Shimoda who rejects his diplomatic status, prompting a cultural split in Japan’s mistrust in the influence of the west. Through all the social and political clashes, Harris meets a 17-year-old geisha by the name of Okichi, falling in love with her while she aides him in softening the division. Wayne was 51 at the time.

5 Tycoon

Hired by a South American tycoon Frederick Alexander (Cedric Hardwicke) to construct a tunnel through the Andes Mountains, American engineer Johnny Munroe (John Wayne) falls in love with Alexander’s daughter, Maura (Laraine Day). As Munroe faces challenges in making progress in the job he was assigned to complete, he also faces opposition in convincing the overprotective father of Maura (and his boss) that he is a worthy suitor for the man’s (20 years younger) daughter. Tycoon, like The Barbarian and the Geisha, feeds the male ego and fantasy of viewers, presenting Wayne (and the all-American male) as a sex symbol for much younger women.

4 Island in the Sky

Island in the Sky incorporates pieces of experiences from pilot Ernest Gann (later related in his 1961 autobiographical book Fate is the Hunter) emphasizing his flying career. In this World War II movie, Gann and the pilots he traveled with search for a lost pilot of the team in northern Canada. In the film, Capt. Dooley (John Wayne) has to crash-land his plane in the icy landscape of Canada. While setting out to fly supplies in England during World War II, Dooley and his crew fight to survive in the unfamiliar territory. Though it’s an ensemble film, Wayne continues his white-knight heroic approach to narrative form.

3 The Three Musketeers

The Three Musketeers, a modernized version of the classic tale, finds American fighter pilot Lt. Tom Wayne (John Wayne) traveling to visit his romantic love interest, Elaine Corday (Ruth Hall). Along the way, he gets involved in the war taking place in the Sahara Desert (between the French Legion and a group of Arabic arms smugglers) to rescue a group of legionnaires who were besieged by the opposition fighters. Tom’s new friends recruit him in order to help them efficiently identify the mole secretly working for the Arabic group, so long as they can survive the desert in an almost ‘characters against nature’ way. Again, the film glorifies and romanticizes the heroics of American militarism and the white-knight trope.

2 Allegheny Uprising

Jim Smith (John Wayne) leads a militant group throughout colonial America, setting out to discover who is supplying the area of Native American tribes with various key weapons. Smith suspects Ralph Callendar (Brian Donlevy) to be the traitor among the group, but there has not yet been any proof to support this theory. He strives to pinpoint the corruption among him and his team, as the British commander Capt. Swanson (George Sanders) disregards his concerns. Allegheny Uprising taps into the American fantasy and paranoia of fighting the British and colonizing Natives, and Wayne fits in perfectly.

1 Rio Lobo

The American Western Rio Lobo is set in a post-Civil War environment, and was the last film directed by the legendary Howard Hawks, concluding his American trilogy of Westerns preceded by Rio Bravo and El Dorado, which all uses the West to explore identity. As Cord McNally (John Wayne), a local Union leader, protects an incoming gold shipment, his fellow troops are suddenly attacked by an influx of Confederate forces. In this encounter, McNally looses the gold he was supposed to protect as well as his friend and officer who was killed in the raid. As McNally travels to the town of Rio Lobo, he learns the Confederate forces had direct help from the inside of his team. In his visit, McNally sets out to learn the identity of the traitors. Released in 1970, Wayne was playing to a wholly different American culture that had passed him by, and the film was a box office failure. He would make his Playboy comments the next year.