Oscar Answer #6

Oscar Answer No. 6
That’s Barry Fitzgerald (right, with Bing Crosby and Rise Stevens), who received best actor and best supporting actor nominations for his role as the cranky but golden-hearted elderly priest in Leo McCarey’s syrupy Going My Way (1944). Fitzgerald lost the best actor Oscar to Bing Crosby, the official star of Going My Way, but won the best supporting actor award.
Academy rules were then changed to prevent any more double nominations for the same role.
Other performers who have been nominated in the same year, but for different films, are:

Fay Bainter in 1938 (lead in White Banners, supporting in Jezebel);
Teresa Wright in 1942 (lead in The Pride of the Yankees, supporting in Mrs. [...]

Oscar Answers #3, 4, 5

Oscar Answer No. 3
John Huston (right), from Moulin Rouge (1952) to Prizzi’s Honor (1985), a total of 33 years.
In 1952, Huston lost the Oscar to John Ford for The Quiet Man, and in 1985 to Sydney Pollack for Out of Africa. Huston, however, did win for The Treasure of the Sierra Madre (1948).
Roman Polanski comes in second, from Tess (1980) to The Pianist (2002), 22 years; and Joseph L. Mankiewicz in third, from 5 Fingers (1952) to Sleuth (1972), 20 years.
In fourth place, with a 19-year gap between nominations, it’s a tie: Otto Preminger, from Laura in 1944 to The Cardinal in 1963; and David Lean, from Doctor Zhivago in 1965 to A Passage to [...]

Oscar Answers #1 & 2

Before looking at the answers, you may want to test your Oscar knowledge — or lack thereof — by checking out the Oscar Quiz first.
 
Oscar Answer No. 1
William Wyler (right). From Walter Brennan* to Barbra Streisand, Wyler directed 36 Oscar-nominated performances.
Elia Kazan comes in second place, with 24 nominations; George Cukor in third, with 21; and both Fred Zinnemann and Martin Scorsese in fourth, with 20.
* Following some serious "creative differences" with producer Samuel Goldwyn, Howard Hawks was replaced by William Wyler during the making of the 1936 family saga Come and Get It, for which Walter Brennan won the first ever best supporting actor Oscar. Both Wyler and Hawks shared directorial credit for the film.
 

Henry Fonda, Jane [...]