20. Dane Cook as Mr. Smith
Mr. Brooks (2007)
Kevin Costner's serial killer thriller, Mr. Brooks, is a criminally underrated, highly enjoyable B-movie, and while Costner and William Hurt unsurprisingly steal the show, it's Dane Cook of all people who surprises with a complete left-field portrayal as a truly sick deviant eager for Costner's Brooks to school him in homicide.
There is truly no trace of the wise-cracking foul mouth from Retaliation, and Cook's shitty film selection since then has been a real letdown. Chill with the rom-coms and get another script like this, bro.