Year: 1960
Nominees: "The 400 Blows" (Francois Truffaut and Marcel Moussy), "North by Northwest" (Ernest Lehman), "Operation Petticoat" (Paul King, Joseph Stone, Stanley Shapiro and Maurice Richlin), "Pillow Talk" (Russell Rouse, Clarence Greene, Stanley Shapiro and Maurice Richlin), "Wild Strawberries" (Ingmar Bergman)
What won: "Pillow Talk"
What should have: "The 400 Blows"... or "North by Northwest"... or "Wild Strawberries"
Why: I know, I know... we tend to rag on the Academy for not recognizing comedy often enough, and here I go picking on them for a relatively unusual comic choice. Risque for the time, this amiable Doris Day-Rock Hudson romcom looks distinctly tame, and more than a little creaky, these days -- but even in 1960, it must have seemed a slight choice given the competition, which just happens to include three of the greatest films of all time. It's not surprising that voters weren't ready to reward the New Wave jazz of Truffaut's "The 400 Blows" or the stark emotional austerity of Bergman's "Wild Strawberries," but how could they resist the pure Hollywood joy of "North by Northwest," one of the tightest and spryest scripts Hitchcock was ever given to work with?

-Guy Lodge