23. Nicky, Little Nicky (2000)
Played by: Adam Sandler
When coming up with the most annoying characters in movies, we have the veritable pick of the litter in Adam Sandler's consistently grating roles, but nothing even comes close to his turn in Little Nicky. Complete with a bad haircut and a torturous speech impediment, Sandler’s performance made every moment of the movie pure agony.
It seemed like the success of the film was predicated on Sandler’s bizarre accent for Nicky, the devil's son, but that character choice proved to be unbearable after a few minutes. Unfortunately, the movie then dragged on for an hour and a half. Sandler absolutely ruled the ‘90s, but his first movie of the new millennium seemingly set the tone for what was his eventual fall from grace.