8. Gran Torino (2008)
This is the biggest omission by the Academy on this list, and possibly ever. Two years prior, "Letters From Iwo Jima" was nominated for Best Picture and Directing (lost both to "The Departed" and Martin Scorsese). And two years prior to that, Mr. Eastwood received Oscar nods for Best Picture, Directing, and Actor in a Leading Role for "Million Dollar Baby." He won Best Picture and Director, the second time in his career. He was also nominated for Best Picture and Director for "Mystic River." So of the movies that received nominations, they win big if Clint Eastwood is in the leading role. Or any role for that matter. He had the lead role in "Gran Torino." He was also the only big name actor in the movie. The 2009 ceremony was highly contested and memorable. I would've swapped "Gran Torino" for "The Reader" in the Best Picture category and Clint Eastwood for Stephen Daldry ("The Reader") in the Directing category. I also would've nominated Tom Stern in the Cinematography category in place of himself for "Changeling." I would even take Michael Shannon for "Revolutionary Road" out of the Best Supporting Actor category in favor of Bee Vang for his performance as Thao. And Nick Schenk would get a nod for Best Original Screenplay instead of Martin McDonagh for "In Bruges." It was originally written to take place in Minneapolis, MN and set to be filmed in the Northeast area. But aside from changing the location and references in the film from Minneapolis to Detroit, MI for financial reasons, Clint Eastwood and his production crew decided to leave the script as it was.