10. MR. BEEFY THE BULLDOG IN LITTLE NICKY (2000)
Looking back on Adam Sandler’s filmography, there’s a bevy of underwhelming comedies, yet none maintains as much of an air of flat-out stupidity as Little Nicky. Nearly everything about the high-concept mess is off, namely Sandler’s irritating turn as a mousy Devil’s son cast upon Earth to fight his evil brothers. He mumbles dialogue like there’s a pound of Skippy in his gums, rarely makes eye contact with his co-stars, and doesn’t say a single funny thing. Other than that, though, he’s money.
It’s up to a foul-mouthed bulldog named Mr. Beefy (we dare you to call one of your male friends that) to rescue its few scenes from total embarrassment; thankfully, Sir Beef (that’s not much better) received the few moments of cleverness that appear in Little Nicky. Hearing a demonically possessed canine emit creepy kid chants instead of snores doesn’t exactly qualify as comedic brilliance, yet it’s an appreciated distraction from watching Sandler’s worst character of all time.