Lewis Milestone won the only Oscar ever given for Comedy Direction in 1927/28, for Two Arabian Knights which was not included among the Best Picture nominations (the only other director in competition for the award was Ted Wilde for Speedy after original nominee Charlie Chaplin was removed in the final voting when he was instead given a special award for The Circus). Milestone won a second Best Director Oscar two years later for the first true masterpiece of the sound era, All Quiet on the Western Front, which did win the Best Picture Oscar. His only other nomination was for directing The Front Page (1931) despite a long career which included such Best Picture nominees as Of Mice and Men (1939) and Mutiny on the Bounty (1962).

Frank Lloyd won the Best Director Oscar in 1928/29 for his work on The Divine Lady, which was not nominated for Best Picture (he was also nominated that year for Weary River and Drag, neither of which was nominated for Best Picture, which was won by MGM's The Broadway Melody). He won a second Best Director for 1933's Best Picture winner Cavalcade and his Oscar tally evened out in 1935 when his film Mutiny On the Bounty won Best Picture, and he lost the Best Director award to John Ford for The Informer.The Academy virtually turned its back on his films after that (he had directed one previous Best Picture nominee, East Lynne in 1931; one of the few films to be nominated in that category and no others), although he did direct Basil Rathbone to a Best Supporting Actor nomination in If I Were King in 1938.

Milestone is a bit of a cheat since the Academy (in a characteristic move) considers his win for Comedy Direction not to be on the same level as the winner for Best Director in that first year (it is telling that they didn't make the distinction between "Comedy Direction" and "Dramatic Direction," but simply "Comedy Direction" and "Direction"), so any hardcore Oscar trivialists who didn't include him in the answer get full credit.