3. Little Nicky (2000)
With Little Nicky, almost as though he was fighting against the criticism that he always plays himself, Sandler seemed to attempt something completely out of his comfort zone. Essentially his character here is a hell-spawn demon with a speech impediment. Admittedly, you cant really get further from Happy Gilmore than that. However, the main problem with Little Nicky is that, as a character and as a turned in performance, hes probably the most grating and gimmicky in the entire Sandler canon. Hes clearly not all that comfortable putting on Nickys silly rasping voice, or holding that sideways grimace the whole time; you could probably argue that Little Nicky would have been infinitely more watchable if hed just scrapped the whole gimmick and gone full on Happy Gilmore with it. But not, he stays the course, which I suppose you should give him
some credit for. However, performance wise, Sandler is far from on fire here, which is ironic considering hes supposed to be from Hell.