Director Lewis Milestone could count a few Academy Award firsts during his lengthy career.
Milestone won the first ever Oscar for directing, in 1928, for "Two Arabian Knights". He beat out some guy named Charlie Chaplin. There were actually two directing winners that year (and only that year), for the Oscars gave out two trophies: one for comedy and one for drama. So Milestone is the only one to ever win Best Director (Comedy).
In 1930, Milestone became the first person ever to win two directing Oscars. His second came for "All Quiet on the Western Front".
Together with Ben Hecht and Benjamin Glazer, who both won Best Writing awards (Original and Adaptation) in 1928, Milestone was the first ever Jew to win an Oscar.
Quite important milestones!