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 Darwell in The Grapes of Wrath
Answer No. 2
Henry Fonda, from The Grapes of Wrath (1940) to On Golden Pond (1981, right), a total of 41 years.
Fonda lost the 1940 Oscar to James Stewart for The Philadelphia Story, but he won the statuette the second time around.
Helen Hayes, Jack Palance, and Alan Arkin tie for second place, with a 38-year nomination gap. Hayes from The Sin of Madelon Claudet (1931-32*) to Airport (supporting, 1970); Palance, both supporting, from Shane (1953) to City Slickers (1991); and Arkin from The Heart Is a Lonely Hunter (1968) to Little Miss Sunshine (supporting, 2006).
Ralph Richardson comes in fifth, both in the supporting category, from The Heiress (1949) to Greystoke: The Legend of Tarzan, Lord of the Apes (1984), 35 years; and Lynn Redgrave in sixth, from Georgy Girl (1966) to Gods and Monsters (1998), 32 years.
* The Oscars only began covering films released during a calendar year in 1934.