The Best Villain Ever Written: Douglas Fairbanks, Jr. as Rupert of Hentzau in ‘The Prisoner of Zenda’

The Prisoner of Zenda had a great impact on the film career of Douglas Fairbanks, Jr. For one, it kicked off a swashbuckling trend in his career that continued into the 1940s. Whether swashing was a learned or an inherent skill, it came naturally for Fairbanks and he made it look effortless in all of his films. He possessed the same grace, agility, and athleticism that his father had in his famous swashbuckling roles. But Zenda proved more than his knack for swashbuckling. It also showed that Fairbanks had what it took to inhabit the dark side. He played a villain with a unique style that made him both charming and menacing at the same time. Many would argue that our fascination with villains in film comes from our own intrigue and curiosity about the darkness that lurks within us all. Fairbanks as Rupert of Hentzau is the perfect example of this as he lures us in with his charm while still sending a cold shiver down our spine.

Throughout the 1920s and 30s, Fairbanks avoided swashbuckler roles so as not to be compared to his father. Douglas Fairbanks, Sr. found great success as Hollywood’s first swashbuckler and did not want his only son to follow in his acting footsteps. Fairbanks, Jr.’s entrance into the film industry was a source of frustration between he and his father in the 1920s and Fairbanks, Jr. wanted to prove to film audiences (and his father) that he was his own man. In doing so, he made up his mind to reject any offers that were of the swashbuckling genre.


(Source: x)

But in 1937, Fairbanks received an offer from David O. Selznick that was hard to refuse. It was for the role of Count Rupert of Hentzau, the villain in the The Prisoner of Zenda. As appealing as the offer was, there were two major issues. First of all, Fairbanks would not be receiving top billing which he believed he deserved at this point in his career. Fairbanks had moved abroad in the early 1930s to create his own film company called Criterion. Ever since he had become his own boss, he felt that he shouldn’t accept anything less than top billing. Ronald Colman was set to be the leading man of Zenda which left Fairbanks in a supporting role. He wrote, “…I was set back on my heels at being asked to be a supporting or featured player to anyone – even so fine an actor as Ronald Colman. I quickly reviewed the years I had taken to become a star and recalled the long struggle to be my own boss – made possibly only by going abroad.”1 Furthermore, he was still determined to not be a carbon copy of his father by accepting a swashbuckler role. Selznick begged him to consider the role and assured him that he would not cast anyone else until Fairbanks had made up his mind.

The offer troubled Fairbanks enough for him to ask his father for advice on the issue. Asking his father for career advice was not common for Fairbanks and he was surprised by his father’s reaction. “When I finished, he burst out with the conviction that I had to accept.”2 Skeptical of his father’s insistence, Fairbanks inquired as to why he had to accept the role. His father responded with his signature enthusiasm:

‘Because not only is The Prisoner of Zenda one of the best romances written in a hundred years and always a success, but Rupert of Hentzau is probably one of the best villains ever written. He is witty, irresistable, and as sly as Iago…Whoever plays Rupert, in any stage production in any country, will always be a big hit, even though the leading part is a double role. If you play this part of Rupert, people will forget any slump you’ve had. You’ll be on top again right away!…That part is known to be actor-proof! Nobody has ever played Rupert and failed to steal the show, on either stage or screen! It is so actor-proof, in fact, that Rin-Tin-Tin could play the part and walk away with it!’3

Needless to say, Fairbanks was convinced! He knew that he must accept the role and immediately called Selznick to say yes to the offer. There was just one thing he still needed to fix. He was still unhappy with the fact that he would not be receiving top billing so he asked Selznick for special billing. He suggested that “With Douglas Fairbanks, Jr., as Rupert of Hentzau” be placed at the bottom of the billing in big letters. Selznick agreed and Fairbanks began work on Zenda in Hollywood.

Douglas Fairbanks, Sr. and Douglas Fairbanks, Jr.

It wasn’t often that Fairbanks sought film career advice from his father but we’re mighty glad he did for “Zenda”. Above: Fairbanks, Sr. and Jr. on set of “Jump For Glory,” 1936. (Source: x)

The Prisoner of Zenda is a story by Anthony Hope that includes deception, adventure, and romance. In Ruritania, King Rudolf V (Ronald Colman) meets a distant English cousin, Major Rudolf Rassendyll (Ronald Colman), who happens to be his look-a-like. The King’s brother, Black Michael (Raymond Massey), drugs the king the night before coronation in an attempt to steal the crown. Instead, Major Rudolf Rassendyll poses as the king for coronation day while King Rudolf V lays unconscious in the cellar. Things continue to get twisted as Rassendyll, posing as the king, falls in love with Princess Flavia (Madeleine Carroll), the intended Queen of Ruritania. Rupert of Hentzau (Douglas Fairbanks, Jr.) enters as the villain who is seemingly on the side of Black Michael but is really after Lady Antoniette (Mary Astor), King Rudolf V’s mistress. The chaos reaches a climax when Lady Antoinette agrees to help Rasendyll save the king and Rupert turns his back on Black Michael by killing him. Once Rupert is aware that Lady Antoinette has agreed to save the king, violence ensues and an epic sword fight takes place between Rupert and Rassendyll. In the end, King Rudolf V is saved and becomes a kinder leader as a result. The only remaining problem is that Princess Flavia is still in love with Rassendyll, not King Rudolf V. But staying true to her country and her new role as Queen of Ruritania, she agrees to leave Rassendyll and fulfill her marriage to King Rudolf V.

Fairbanks took creative control over the look of Rupert of Hentzau. He made an important decision based on the advice of his father that one should never wear anything too distracting around the neck and should dress simple and in contrast to the other actors. Since Ronald Colman would be dressed in Balkan uniforms that were elaborate and showy, Fairbanks decided he would wear black basic uniforms that were simple. He later wrote, “After a few camera tests, I convinced both producer and director that the relative simplicity of my dark costumes would be more menacing and also more conspicuous.”4 He also made the decision to wear his hair curly. Both decisions were crucial to Fairbanks’ characterization of Rupert. He stands out throughout the film by exuding a darkness that makes him without doubt the villain of the movie.


Fairbanks in all black and looking menacing as Rupert of Hentzau. (Source: x)

The Prisoner of Zenda also broke Fairbanks’ no swashbuckling rule that he had long adhered to by featuring his first sword fight on the big screen. Fairbanks wrote, “The circumstances of the story in which I played a villain and the fact that it had been ten years since my father had last swashed a silent movie sword, eased my apprehensions.”5 Selznick hired one of the best sword fighting instructors in Hollywood named Ralph Faulkner to help Fairbanks and Colman with the scene. For Fairbanks, sword fighting came naturally because he had spent years fencing when he was younger. Colman, on the other hand, had little experience and Faulkner doubled for him in medium and long shots. The sword fight scene is crucial to the film and Selznick slaved over the sequence by rewriting it over and over to ensure that it was exhilarating. The hard work put forward by Fairbanks, Colman, Selznick, and Faulkner proved to be worthwhile. As Fairbanks wrote, “It turned out to be one of the screen’s classic sword-fight sequences.”6 (The clip below features the great sword fight)


Fairbanks and Colman sword fighting. (Source: Personal Collection)

In the end, Fairbanks’ decision to play Rupert of Hentzau proved to be a smart move. The film received stellar reviews and Fairbanks himself received all good reviews. He later wrote, “For the first and only time in my memory I didn’t get one bad or even indifferent review – nor, indeed, did Ronnie.”7 Also true to his father’s word, Fairbanks received a substantial amount of film offers due to the success of The Prisoner of Zenda. In addition to rave reviews, the film was nominated for two Academy Awards in the Best Art Direction and Best Music, Score categories. The fantastic cast consists of several great actors that make every role worthy of mention including David Niven, C. Aubrey Smith, Raymond Massey, Mary Astor, and Madeleine Carroll in addition to Colman and Fairbanks. But it is Fairbanks that truly stands out in this film. So much so that Selznick even considered following it up with a sequel based on the novel Rupert of Hentzau, also by Anthony Hope. Unfortunately, the sequel never came to be but the offer emphasized just how impressive Fairbanks was as Rupert.

It is hard to imagine what The Prisoner of Zenda would have been like if Fairbanks had not taken the advice of his father. In my humble opinion, his portrayal of Rupert of Hentzau is the best of all the other screen portrayals. And that’s saying a lot considering the other two brilliant actors, Ramon Novarro and James Mason, who portrayed him. Fairbanks gives Rupert a rare quality that makes him all at once both likeable and frightening. It is this quality that I believe makes the greatest villains of all time and Fairbanks deserves to be remembered and celebrated for his role as one of the best villains ever written, Count Rupert of Hentzau.


(Source: x)


***This piece was written for The Great Villain Blogathon hosted by Speakeasy, Silver Screenings, and Shadows and Satin (click below to go to the blogathon!)

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  1. Douglas Fairbanks, Jr., The Salad Days (New York: Doubleday, 1988), 271.
  2. Ibid, 271.
  3. Ibid, 271-272.
  4. Ibid, 274.
  5. Ibid, 276.
  6. Ibid, 276.
  7. Ibid, 276.

Additional Sources:

11 thoughts on “The Best Villain Ever Written: Douglas Fairbanks, Jr. as Rupert of Hentzau in ‘The Prisoner of Zenda’

  1. Agreed! Rupert of Hentzau is a terrific villain and, like you said, playing this character was a very smart move by Fairbanks Jr.

    Thanks for sharing all your research with us – and thanks for bringing the handsome Rupert to the Villain Blogathon!

    Liked by 1 person

  2. Great to read all the history and behind-the-scenes of this film. Your research and knowledge is amazing! It was especially interesting to read about the interest he took in his own costuming and his decision to wear relatively simple uniforms for contrast.

    I actually saw the remake with James Mason first, but the ’37, as you say, is superior in so many ways, especially with Fairbanks, Jr. I am very curious to see the silent film sometime.

    Liked by 1 person

    • Thank you for reading and for the compliments! I really appreciate it. I’m so glad he made the choice in his costuming because I think it definitely did have the desired effect. It’s a great story and fun to watch in all of its versions but this one is definitely the best of the three. Thanks again!

      Liked by 1 person

  3. So I haven’t seen all of Fairbanks’ roles but I think this is one of my favourite – I completely agree that he manages to be both charming and chilling. Was great to read all your other research too – such an interesting insight about the costume!

    Liked by 1 person

  4. Wonderful post on one of my favorite actors’ most delicious movies! Fairbanks’ Rupert is irresistible. I don’t know how he felt doing it but he *looks* like he’s having a grand time, as he should be—he walks off with it, and that’s not a small thing with Colman giving one of his most winning performances and the rest of the fabulous cast.

    Liked by 1 person

    • I absolutely agree! I think he definitely enjoyed the role. I understand why he avoided swashbuckling roles but he plays them so naturally. He’s absolutely beautiful as Rupert. Thank you so much for reading!


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