1927-28 Oscar Winner Emil Jannings was a bit Strange.

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The first person ever presented with an Academy Award was Emil Jannings, a silent-film actor who took the Best Actor award for two films.
The first, 1928’s “The Last Command,” told the tale of a brave Russian Czarist commander reduced to squeaking by as a Hollywood extra.
The second, 1927’s “The Way of All Flesh,” starred Jannings as a happy bank clerk who gets bamboozled by a femme fatale and ends up a tramp. (Sensing a theme?)
Jannings’ Oscar win is chock-full of weirdness.
He won in the only year that awards were given for multiple performances; there are no surviving copies of “The Way of All Flesh,” so the film is entirely lost; and according to legend, the famous German Shepherd Rin Tin Tin actually got more votes for the prize than Jannings.
(The rumor is hard to substantiate outside of modern news reports poking fun at the Academy.)
Perhaps most surprising to modern eyes, though, is what Jannings did after he won his Award.
A native German, Jannings returned to his home country and starred in several Nazi propaganda films.
via 5 Weird Facts About the Oscars : Discovery News.

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