12. Butterfield 8 (1960)
Award won: Best Actress (Elizabeth Taylor)
Fans of Denzel Washington and Martin Scorsese understand that their respective Oscar victories (for Training Day and The Departed, respectively) were well-deserved from a career perspective, but, unfortunately, awarded for the wrong movies. It's reassuring to know that both of them finally took home statues, but it's also frustrating to think that their numerous earlier works weren't the benefactors.
The same thing happened with Elizabeth Taylor decades prior, when the acclaimed actress snagged the Best Actress honor after there previous nominations that yielded no golden hardware. Taylor's victory lap came from Butterfield 8, a tawdry drama in which she played a model who moonlights as a prostitute. As they say, sex sells, even when it comes to getting the Academy to reward one of cinema's all-time greatest actresses.
How did Taylor herself feel about Butterfield 8? She was once famously quoted as remembering the picture with, "I still say it stinks."