13. Around the World in 80 Days (1956)
Awards won: Best Picture, Best Cinematography, Best Film Editing, Best Music, Best Adapted Screenplay
Many critics and Oscar buffs cite Around the World in 80 Days as the worst Best Picture winner of all time. Though we're not immediately inclined to agree (as this list points out, there have been some god-awful Best Picture recipients over the years), that doesn't mean this overcrowded, predictable comedy deserves a pass.
On the contrary, Around the World in 80 Days is a shallow, hokey, and painfully long (141 minutes, to be exact) exercise in excess. As if to only distract viewers from the film's goofiness, a cavalcade of big-name cameos proceeds throughout the picture, including Frank Sinatra and Buster Keaton. None of whom, mind you, serve any purpose other than causing A-list diversions.