The National Board of Review have their film awards out today, and they evidently really, really like Clint Eastwood. Both his efforts this year, Changeling and Gran Torino, made their list of top 10 films of the year, and for the latter they also awarded him best actor and screenwriter Nick Schenk best original screenplay. Now, I'm a longtime Eastwood defender, but these were two of the worst films I saw all year. (You can read my Changeling review here; I'll write about Gran Torino when it opens locally, but the Eastwood-sung theme song might give you some sense of what to expect.)
I'd say the likeliest explanation is that no one on the board bothered to see either movie and they just gave the awards as a kind of perennial sinecure: They named Mystic River best picture in 2003, Letters from Iwo Jima best picture in 2006 (Flags of Our Fathers also made their top ten), and gave Clint a "special filmmaking achievement" award for Million Dollar Baby in 2004.
Alternatively, maybe he gave them the .44 magnum speech and they didn't feel lucky: