Petty thief Rocky Valentine breaks into a loan shop, knocks out the owner, and steals the contents of the safe. The police come down the street and Rocky runs out into the nearby alleyway. As he tries to climb the fence, the policeman shoots and kills him. A white-dressed man steps out of the shadows and suggests that Rocky get up, addressing him by name. A very surprised Rocky looks up and asks who he is, and the man says that his name is Pip. He's there to act as Rocky's guide, and explains that he knows everything about him. Pip takes out a notebook with Rocky's life written down, and explains that his job is to make sure that Rocky gets everything that he wants. He assures Rocky that there's no cost, and the thief pulls out a gun and tries to hold him up. Pip cheerfully hands Rocky $700 and says that there's much more if Rocky will come with him.
Pip escorts Rocky to an expensive apartment and explains that it belongs to Rocky. A suspicious Rocky confirms that everything is just like Pip says, and demands to know what he has to do in return. Pip says that he can't explain any further, and says that he works for someone else. When Rocky demands to see Pip's boss, Pip says that he'll have to wait. As Rocky sits down to wait, Pip starts picking out clothing for him. He knows Rocky's personal preferences, but Rocky soon starts picking out better clothing for himself. Once he finishes, he discovers an expensive meal waiting for him. Rocky suspects that it's poisoned and orders Pip to try it, but the man says that he hasn't had to eat in three centuries and has forgotten how. Rocky figures that it's a set up and shoots Pip in the chest, but the bullets have no effect. Surprised, Rocky shoots at a lamp and confirms that his gun works.
Rocky sits down and picks up a drink, and then wonders how the drink has suddenly appeared out of nowhere. Realizing something is wrong, the thief demands answers. Pip explains that Rocky is dead, and the thief assumes that since he's getting everything he wants, he must be in Heaven and Pip is his guardian angel. Rocky asks for a million dollars and a stacked blonde. Pip directs him to a drawer filled with the million dollars, and a woman appears out of nowhere to dance for Rocky. Laughing, Rocky tells Pip that he'll want more, but right now he wants to enjoy what he has.
Next, Pip and Rocky go to a casino. Rocky plays roulette and keeps winning. He then goes to a slot machine and wins on the first pull. As he goes outside with his three women and Pip, a policeman walks by. The short Rocky complains that the policeman thinks that he's tough just because he's taller, and Pip apologizes for the oversight. He snaps his fingers and the policeman shrinks down to dwarf size.
Rocky and Pip go back to Rocky's apartment, and the thief talks to Pip privately. He wants to look up some of his old friends, but Pip explains that the entire world is tailored to Rocky. Rocky realizes that the women and everyone else are just props to do what he wants. He wonders how he got into Heaven, and figures that he must have done something incredibly good to make up for all the evil things he's done. However, Rocky can't think of anything. He asks if they can find out what, and Pip offers to take him to the Hall of Records. They get there and Rocky goes through his file, but he can't find anything that would get him into Heaven. The thief figures that he's better off not questioning God if God wants him in Heaven. Pip wishes him well and tells Rocky to call him if he needs everything.
Rocky goes back to playing at the casino, and keeps winning over and over again. He takes the women back to his bedroom to play poker, but he still wins with a royal flush even when they draw a straight flush. Rocky yells at them to get out and finds a pool table in his living room. He makes a single shot and every ball lands in a pocket.
Disgusted, Rocky calls Pip, who appears in the apartment. Pip asks what's wrong and Rocky explains that he's bored with winning all the time. The guide suggests that he arrange for Rocky to lose, and Rocky says that it wouldn't be the same if he knew it was going to happen. Pip then suggests that Rocky go back to his old profession, and Rocky eagerly agrees. However, he quickly realizes that he can't fail at that either, unless Pip arranges for him to be captured. Desperate, Rocky tries to explain to Pip about the fact that life is deadly dull if there's no chance of losing. He admits that he doesn't belong in Heaven, and figures that he'd be better off in the "other place." Laughing, Pip tells him that Rocky is in the Other Place. Realizing what his Hell will be, Rocky tries to leave without success as Pip's maniacal laughter echoes in his ears.