Little Nicky (2000)

Synopsis
The youngest child of the family often has the most problems -- so why should things be different for the Prince of Darkness and his offspring? Satan (Harvey Keitel) is considering retirement, and is pondering which of his sons should take over the family business -- ambitious Adrian (Rhys Ifans), strapping Cassius (Tommy "Tiny" Lister Jr.), or Nicky (Adam Sandler), an accident-prone demon who prefers to stay in his room playing his favorite heavy metal tunes. When Satan decides to stay on for another 10,000 years, Adrian is outraged, and leaves Hell to go to New York, where he and Cassius attempt to round up enough souls to vote Satan out of power. Satan, understandably upset, sends Nicky to bring Adrian and Cassius back home, but Nicky finds life on Earth is more complicated than he expected. Things don't get any easier when he develops a crush on Valerie (Patricia Arquette), a good-hearted mortal woman. Little Nicky also features Michael McKean as a city official trying to put Nicky behind bars, Kevin Nealon as Hell's gatekeeper, Rodney Dangerfield as Satan's father, Robert Smigel as the voice of Beefy -- a talking dog who is Nicky's guide on earth, Allen Covert as Todd -- Nicky's new roommate, and Peter Dante and Jonathan Loughran as a pair of metalheads who dig Satan. Jon Lovitz and Reese Witherspoon play cameo roles, and Regis Philbin and Ozzy Osbourne appear as themselves. ~ Mark Deming, All Movie Guide