Awards won: Best Picture, Best Story (the precursor to Best Original Screenplay)

It almost feels like sacrilege to include Cecil B. DeMille on any list tinged with negativity. After all, he's the Hollywood icon and original blockbuster champ behind landmark motion pictures like Cleopatra (1934) and Samson and Delilah (1939). Yet the man slipped up big-time once, and, as painful as it is to acknowledge, it was quite the folly.

Considered one of the worst movies to ever win the Best Picture honor from the Oscar committee, DeMille's The Greatest Show on Earth is an overlong (two-and-a-half hours, to be exact) and virtually plot-less look at shenanigans at a large-scale circus. It's a tedious soap opera disguised as lavish spectacle, one that's led by an overcharged Charlton Heston and might provide some fun for little kids who beg their parents to visit Barnum & Bailey's.

All's well that ends well: DeMille avenged his reputation four years later with the monumental The Ten Commandments, the last movie he made before passing away in 1959.