That's the question Washington Post film critic Stephen Hunter asks about Martin Scorsese in this article. He writes,
"That's the question for the great director Martin Scorsese, who has been five times nominated for a Best Directing Oscar and has never won. Now, his film "The Departed" will almost certainly be nominated Jan. 23 in a number of categories, directing among them, and the question is: Will he at last get to make the speech with the golden statuette in his hand, signifying whatever it is that an Oscar signifies?"
Hunter argues that Scorsese should be receiving not his first, but his third Oscar. Hunter says he should have won in 1980 for "Raging Bull" (other nominees included winner Robert Redford, "Ordinary People," David Lynch, "The Elephant Man," Richard Bush, "The Stunt Man," and Roman Polanski, "Tess") and again in 1990 when Scorsese lost for his film "Goodfellas" to Kevin Coster for his "Dances with Wolves" (other nominees were Francis Ford Coppola, "The Godfather Part III," Stephen Frears, "The Grifters," and Barbet Schroeder, "Reversal of Fortune").
It's hard to disagree with either, and I'm still mystified that the Academy snubbed him for a Best Director nomination in 1976 for "Taxi Driver." In 1988, Scorsese was nominated for "The Last Temptation of Christ" and lost to Barry Levinson who directed "Rain Main." Hard to argue with that one. In 2002, Scorsese was nominated for "Gangs of New York," and lost to Roman Polaski for "The Pianist." Again, hard to argue. And in 2004, Scorsese, nominated for the 5th time for "The Aviator" (I film I thought sucked) lost to Clint Eastwood for "Million Dollar Baby."
What I think is interesting is all the films for which Scorsese missed a nomination. I mentioned "Taxi Driver," but what about perhaps his best film "Mean Streets" in 1973 (nominees were Ingmar Bergman, "Cries and Whispers," George Roy Hill, "The Sting," Bernardo Bertolluci, "Last Tango in Paris," William Friedken, "The Exorcist," and George Lucas, "American Graffiti") or "The Color of Money," in 1986 (nominees were David Lynch, "Blue Velvet," Woody Allen, "Hannah and Her Sisters," Roland Joffe, "The Mission," Oliver Stone, "Platoon," and James Ivory, "A Room with a View") or "The Age of Innocence" in 1993 (nominees were Jim Sheridan, "In the Name of the Father," Jane Campion "The Piano," James Ivory, "The Remains of the Day," Steven Spielberg, "Schindler's List" and Robert Altman, "Short Cuts") or "Casino" in 1995 (nominees were Chris Noonan, "Babe," Mel Gibson, "Braveheart," Tim Robbins, "Dead Man Walking," Mike Figgis, "Leaving Los Vegas," and Michael Radford, "Il Postino").
Scorsese has his 6th nomination in hand for "The Departed." My money says he wins.