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 [...]

Major Oscar Comebacks

Henry Fonda in The Grapes of Wrath (top); Fonda and Katharine Hepburn in On Golden Pond (bottom)

Below are the performers and directors who had a 20-year or longer gap between Academy Award nominations.
Unless otherwise noted, the nominations are for leading roles; years in bold means Oscar wins.

41 years between nominations
Henry Fonda (1940, The Grapes of Wrath — 1981, On Golden Pond)

38
Helen Hayes (1931-32, The Sin of Madelon Claudet — 1970, supporting, Airport)
Jack Palance (1953, supporting, Shane — 1991, supporting, City Slickers)
Alan Arkin (1968, The Heart Is a Lonely Hunter — 2006, supporting, Little Miss Sunshine)

35
Ralph Richardson (1949, supporting, The Heiress — 1984, supporting, Greystoke: The Legend of Tarzan, Lord of the Apes)

33
John [...]