Woolley was nominated twice for an Academy Award, as Best Actor in 1943 for The Pied Piper and as Best Supporting Actor in 1945 for Since You Went Away.
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To English-speaking audiences, he is known for playing tragic hero characters, such as General Tadamichi Kuribayashi in Letters from Iwo Jima and Lord Katsumoto Moritsugu in The Last Samurai, for which he was nominated for the Academy Award for Best Supporting Actor.
Dean Stockwell was nominated for the Academy Award for Best Supporting Actor, and won awards in the same category from the National Society of Film Critics and the New York Film Critics Circle, both of which were also in honour of his work in Tucker: The Man and His Dream (1988).
Notable guest stars who went on to find success in entertainment included Vera Miles, costar of Alfred Hitchcock's thriller Psycho, Bob Fosse, later a noted choreographer and director who won multiple Tonys and an Academy Award for his work, and even a child-age Christopher Walken, who became an Oscar-winning actor and screen star, appeared alongside Jerry Lewis in a sketch (albeit under his given name, Ronald).
He was nominated for an Academy Award for best supporting actor in (1973) for his role as Phil Green in Save the Tiger (his co-star Jack Lemmon won for Best Actor).