Choosing out of the 5 nominated films I think the departed deserved the best picture win.
2006:
Babel
The Departed (Deserved to win) (Won)
Letters From Iwo Jima
Little Miss Sunshine
The Queen
2005:
Brokeback Mountain
Capote
Crash (Won)
Good Night, and Good Luck (Deserved to win)
Munich
2004:
The Aviator (Deserved to win)
Finding Neverland
Million Dollar Baby (Won)
Ray
Sideways
2003:
The Lord of the Rings: The Return of the King (Won)
Lost in Translation (Deserved to win)
Master and Commander: The Far Side of the World
Mystic River
Sea Biscuit
2002:
Chicago (Won)
Gangs of New York
The Hours
The Lord of the Rings: The Two Towers (Barely deserved to win, bad oscar year)
The Pianist
2001:
A Beautiful Mind (Won)
Gosford Park
In the Bedroom
The Lord of the Rings: The Fellowship of the Ring (Deserved to win)
Moulin Rouge!
2000:
Gladiator (Deserved to win) (Won)
Chocolat
Crouching Tiger, Hidden Dragon
Erin Brockovich
Traffic
Only 2/7 I felt deserved the win