40. Little Nicky (2000)
A star-studded religious satire that makes a convincing argument for atheism, Little Nicky stars Adam Sandler as the “kindest” son of Satan (Harvey Keitel) who is sent to Earth to keep his brothers from wreaking havoc on a biblical scale. Nothing in Little Nicky, not even a giggling Reese Witherspoon in angel wings, can redeem the movie’s damned soul. A lethally annoying performance by Sandler is arguably the movie’s deadliest sin.