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|Patricia Arquette||Valerie Veran|
|Tommy 'Tiny' Lister||Cassius|
|Robert Smigel||Mr. Beefy|
|Michael McKean||Chief of Police|
|Frank Sivero||Alumni Hall Announcer|
|Henry Winkler||Henry Winkler|
"He's Never Been To Earth. He's Never Even Slept Over Some Other Dude's House."
"If Your Father Was The Devil And Your Mother Was An Angel, You'd Be Messed Up Too."
"Be Unafraid. Be Very Unafraid."
"You know his number. You know his name. And now, you will meet... his son."
"He Walks Among Us November 2000"
"Being Evil Ain't Easy"
The story revolves around a struggle to determine which of Satan's (Harvey Keitel) three sons will succeed their father as ruler of Hell. Adrian (Rhys Ifans) is the most devious, Cassius (Tom Lister Jr.) is the cruelest and Tassadar (Adam Sandler), also known as Little Nicky, is their father's favourite. Adrian and Cassius claim that Nicky's mother is a goat and torment him by controlling his body with their minds. Nicky has had a speech impediment and a disfigured jaw since Cassius hit him in the face with a shovel when he was a child.
Having been the "Prince of Darkness" for ten thousand years, Satan assembles his sons to decide which of them will succeed him, but instead he keeps the throne for himself because his sons are not yet ready to be his successor and he tells them that they need to learn to keep the balance between good and evil. Angered by this decision, Adrian and Cassius go to Earth to create a new Hell by possessing religious and political leaders in New York City. As they leave, they freeze the entrance to Hell, preventing more souls from entering and causing Satan's body to begin decomposing. To stop Adrian and Cassius, Satan sends Nicky to Earth with a silver flask that traps whoever drinks from it inside.
At first, Nicky has trouble staying alive on Earth. He is killed several times, landing in Hell and returning to New York each time. While learning how to eat and sleep, he meets a talking bulldog named Mr. Beefy (voice of Robert Smigel), rents an apartment with an actor named Todd (Allen Covert) and falls in love with a design student named Valerie (Patricia Arquette).
Nicky's first encounter with his brothers occurs when Adrian sees him with Valerie, takes mental control of his body and makes him scare her away. Then Nicky sees Cassius on television, possessing the referee of a Harlem Globetrotters game. When he goes to the court and tricks Cassius into the flask, Satanist metalheads John (Jonathan Loughran) and Peter (Peter Dante) are so thrilled with his performance that they become his devoted fans. That evening, Nicky tries to apologize to Valerie. The meeting goes badly at first, but she accepts him after he explains who he is and why he is on Earth.
The next day, Adrian possesses the Chief of the NYPD (Michael McKean) and accuses Nicky of mass murder using an edited scene from Scarface. Not knowing what to do, Nicky has Todd kill him so he can go back to Hell and ask his father for advice, but his father has trouble hearing because his ears have fallen off and his assistants are in a panic because the midnight deadline to capture Adrian and Cassius is only hours away. Back on Earth again, Nicky and his friends devise a plan to capture Adrian in a subway station, but Adrian discovers their trick. In the ensuing fight, Adrian grabs Valerie and dives onto the track as a train approaches, but Nicky throws her out of the way, leaving himself and Adrian to be killed by the train.
Arriving in Hell just minutes before midnight, Adrian begins the process of taking over Hell by pushing what remains of his father aside and sitting on the throne, rising to Central Park and starting a riotous party. Meanwhile, Nicky wakes up in Heaven as a reward for sacrificing himself and meets his mother (Reese Witherspoon), an angel who tells him he can defeat Adrian with the "Inner Light" he inherited from her. After she gives him a mysterious orb, he goes to Central Park. Adrian appears to win a pitched battle by locking Nicky in the flask and turning himself into a bat, but Nicky escapes from the flask. When he shatters the orb, Ozzy Osbourne appears, bites Adrian's head off and spits it into the flask.
With his brothers captured, Nicky is ready to save his father. After he sins to make sure he goes to Hell, he and Valerie express their love for each other and she kills him. In Hell, Satan regains his body and recommends that Nicky go back to Earth. The film ends a year later, when Nicky and Valerie live in New York with their infant son Zachariah. It is mentioned that John and Peter have died in a plane crash and are now happily living in Hell in Nicky's old room.
Theatrical : 2000-11-10 : United States of America
DVD : 2001-04-24