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The film opens as we see Jon Lovitz being sent to hell for being a peeping Tom. There we meet Kevin Nealon as the gatekeeper and Harvey Keitel as Satan. Satan has three sons, Cassius played by the huge Tommy Lister Jr, Rhys Ifans, playing the handsome yet evil Adrian, and Little Nicky played by Adam Sandler. Nicky is a little slow and has speech impediment caused by a shovel to the head from one of his brothers. Keitel is thinking about giving up his thrown after 10,000 years and placing one of his sons in charge.
He calls his sons together to announce which one will take over hell. He announces that none of the three are capable so he will stay on for another 10,000 years.
Sandler's two brothers are outraged and leave hell, causing the fiery gates to freeze, not allowing any more souls to enter. This lack of souls causes Keitel to slowly die. (well actually, pieces of his body keep falling off) Keitel is furious at Kevin Nealon for allowing the two to leave so he has two big breasts appear on Nealon's head. This gag provides quite a bit of humor as every time we see Nealon throughout the rest of the film he is either having his breasts caressed by other demons or his bra for his new breasts becomes increasingly fancier.
Keitel sends Adam to earth to capture his brothers. They must drink elixir from a fancy flask which will capture the two inside the flask. Once he returns the two, the gates will be opened again and Keitel will be healthy again.
Nicky appears on earth and is instantly hit by a subway and sent back to Hell. After a few trips back and forth (he keeps getting killed) he finally meets a dog that Keitel sets up to show Nicky the ropes.
Nicky meets Valerie (Patricia Arquette) and the two hit it off. Unfortunately, Adrian discovers Nicky on earth and forces Nicky to say mean and rude things to Valerie and she leaves.
Adrian and Cassius are posing as the Mayor and a bishop in New York. Together, they are causing all kinds of havoc on earth. They do things like change the city's motto to "I love Hookers" and lowering the drinking age to 10.
While at home, Nicky sees a Harlem Globetrotter game and realizes that the referee is Cassius. He goes to the game and gets into a confrontation with the ref. Finally, after outplaying him in a one on one type game, the ref asks Nicky how he did it. Nicky tells him it's from his magic elixir and the ref (Cassius) takes a drink and disappears into the flask. One down!
Nicky gets back together with Valerie and explains everything to her. They launch a plan to capture Adrian. Together, Nicky, Valerie and 3 other friends he has picked up along the way, meet Adrian in a subway waiting area. Adrian almost drinks the elixir but figures it out and grabs Valerie and jumps in front of a moving subway.
Nicky jumps down and throws Valerie out of the way but Nicky and Adrian are killed by the train.
This time however, since he did a good deed, Nicky goes to heaven and meets his mother. He had always been told that his mother was a goat but his brothers lied. She is actually an Angel (Reese Witherspoon) and looks beautiful. Angels never age so Reese is still a teenager and acts like one with her friends as she introduces her son to everyone.
They look down on earth to see what's happening and discover that Adrian has taken over Hell and is bringing Hell to New York. A massive rally is taking place and Adrian is the leader performing nasty deeds everywhere including placing thousands of bees on Henry Winkler playing... Henry Winkler.
Reese gives Nicky a glowing ball and sends him back down to earth to capture Adrian.
A fight breaks out and Adrian wins and he forces Nicky to drink the elixir. As Nicky is being sucked into the flask, he grabs Adrian and both of them get sucked in. Now all three brothers are inside the flask and a fight breaks out inside. The crowd gathers around the flask cheering on NIcky as the flasks flips around on the ground. "You can do it NIcky..." shouts Rob Schnieder in his "Waterboy 'outfit.
Finally, Nicky crawls out of the flask and everyone cheers. Turns out however that it is actually Adrian and he taunts everyone as he transforms himself into a bat. The top of the flask is left off and Nicky crawls out. He takes the glowing ball and drops it on the ground and the ball turns into Ozzy Osborne.
Any Ozzy fan knows what going to happen next, right...
Ozzy grabs Adrian the flying bat and bites off his head, spitting it back into the flask.
Now that the two brothers are in the flask, Nicky can return to hell.To do so, someone must kill him, but first he must do an evil deed so he accidentally doesn't go to heaven. He looks at a swollen Henry Winkler and apologizes. Another swarm of bees attack Winkler. Valerie smacks Nicky on the head with a rock, killing him and sending him back to hell.
He saves his father and all is right with Hell again. Keitel takes the flask with Adrian and Cassius in it and shoves it up Hitler's butt.
Nicky returns to earth, marries Valerie and they have a son, Lucifer II.
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