Pinnochio
Roberto Benigni's 2002 adaptation of the classic children's tale was a creepy failure, and for obvious reasons—its producer and director plays an old, balding version of Pinocchio. "What remains is a variant of the nincompoop Benigni persona, here a more annoying, though less angry version of the irresponsible Sandlerian manchild, undercut by the voice of the star of Road Trip," writes Mark Peranson for the Village Voice.
Police Academy 4: Citizens on Patrol (1987)
If there was an award for the least funny movie of all-time, the fourth installment in the Police Academy franchise would surely take home the gold. "What's so amazing about the Police Academy movies is that they keep being made even though they stopped being funny after the hilarious original," writes Kevin Thomas for the Los Angeles Times.