Oscar Directors: Filmmakers with Biggest Number of Oscar Winning Actors in their Films

Jonathan Demme

Directed 4 Oscar Winners

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Four actors from Jonathan Demme’s films made their way to Oscar gold.

First, Mary Steenburgen for Melvin and Howard in 1981; then, Jodie Foster and Anthony Hopkins for the acclaimed The Silence of the Lambs in 1992; and finally, Tom Hanks for Philadelphia in 1994. Each performance is one of the best of each actor’s career, four powerful tours de force that have remained relevant even decades later.

Victor Fleming

Directed 4 Oscar Winners

Victor Fleming was the mind behind some of the most popular movies of the era, a few of which are still as relevant today as they were nearly a century ago. Capable of making epics as massive as Gone With the Wind and more intimate pictures like Dr. Jekyll and Mr. Hyde, he was an exceptional artist whose influence cannot be overstated.

George Cukor

Directed 5 Oscar Winners

Best known for his profound comedies and elegant adaptations of classic literary works, George Cukor was a particularly versatile director back in the age of Classic Hollywood. From The Philadelphia Story to My Fair Lady, Cukor made a number of iconic classics whose incredible casts have aged like fine wine.

Five performances directed by Cukor made their way to the stage of the Academy Awards. These include Jimmy Stewart in one of his most popular roles, The Philadelphia StoryIngrid Bergman for GaslightRonald Colman for A Double LifeJudy Holiday for Born Yesterday, controversially winning over Bette Davis in All About Eve and Gloria Swanson, and Rex Harrison for My Fair Lady.

Acting in the director’s movies always strikes a perfect balance between humor and poignancy, which helps the stories’ tones wonderfully.

Clint Eastwood

Directed 5 Oscar Winners

Though he’s perhaps best known by general audiences as the star of some of the most famous Western films in history, Clint Eastwood has had just as illustrious and celebrated a career behind the camera.

Eastwood is not a fan of wasting anyone’s time on set, so he doesn’t often do more than one take for each shot or scene. Very often, this results in particularly interesting and potent performances, including the five that have won an Oscar: Gene Hackman for UnforgivenSean Penn and Tim Robbins for Mystic River, and Hilary Swank and Morgan Freeman for Million Dollar Baby.

These triumphant performances prove that actors usually do their best when they’re in a Clint Eastwood film.

John Ford

Directed 5 Oscar Winners

Having won four of the five that he was up for, John Ford is the director with the most Best Director Oscar wins. Considering that he’s one of the most influential and acclaimed directors of American cinema, it’s hardly a surprise. Whether he was making an all-timer Western or an adaptation of a classic literary work, Ford always delivered something fresh and interesting in his movies.

Like other all-time greats, John Ford directed five directors all the way to Oscar gloryVictor Mclagen for The InformerThomas Mitchell for StagecoachJane Darwell in The Grapes of WrathDonald Crisp for How Green Was My Valley, and Jack Lemmon in Mister Roberts. The way Ford loved to have his actors swallowed up by their backgrounds in medium and long shots often resulted in really impactful performances that allowed artists to show off their acting chops beautifully.

Fred Zinnemann

Directed 6 Oscar Winners

Fred Zinnemann films are visually elegant, socially aware, and strongly influenced by his background as a documentary filmmaker.

Just like Zinnemann was able to tell stories that came across as genuine and realistic, so too was he a master of getting earnest, believable performances from his actors. In fact, Zinnerman directed some of the most legendary performances in film history, six of which won Oscars. The first was Gary Cooper for High Noon, followed by Frank Sinatra and Donna Reed for From Here to EternityPaul Scofield for A Man of All Seasons, and Jason Robards and Vanessa Redgrave for Julia.

Woody Allen

Directed 7 Oscar Winners

The controversial and disgraced Woody Allen is best known for being the most nominated and awarded screenwriter in Oscar history, with 16 nominations and 3 wins. However, his work as a director has proved to be just as fruitful, as he has led a whopping seven actors to Academy Award nominations since 1978.

The first actress to win an Oscar for an Allen movie is Diane Keaton for her star-making performance in Annie Hall. From there, it’s Dianne Wiest and Michael Caine for Hannah and Her Sisters, Wiest again for Bullets Over BroadwayMira Sorvino for Mighty AphroditePenélope Cruz for Vicky Cristina Barcelona, and most recently, Cate Blanchett for Blue Jasmine, Allen strikes the perfect balance between making his exquisitely written dialogue shine while also allowing his actors ample room to experiment with their characters.

Elia Kazan

Directed 9 Oscar Winners

An incredible nine actors won Oscars for their performances in Kazan movies, including the iconic Vivien Leigh for A Streetcar Named Desire and Marlon Brando for On the Waterfront.

The other seven are James Dunn and Peggy Ann Garner for A Tree Grows in BrooklynKarl Malden and Kim Hunter for StreetcarAnthony Quinn for Viva Zapata!Eva Marie Saint for Waterfront, and Jo Van Fleet for East of Eden.

Kazan revolutionized cinema—namely, the importance that filmmakers put on directing performances—and his contributions to the craft can still be seen today.

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