It happpened like this:
Because they didnīt behave very well at the end of their lives; Leonardo DiCaprio, Brad Pitt and Tom Green were sent to Hell.
Awaiting for their punishments, a voice spoke "Leonardo DiCaprio. Present at door 666". DiCaprio does so and enters the door, only to find the fattest woman ever (The fattest person on Earth wouldn't even compete against her). Then the voice was heard again: "Leonardo DiCaprio; you've been all your life in companion with beautiful women. Now you will be with this monstrosity for all eternity"
And the door closes, not to be open ever again.
Now it's Brad's turn.
"Brad Pitt. Present at door 667" Brad does as he's told and enters the door. He finds the thinnest woman ever (An anorexic person was nothing compared to her)
And the voice spoke again:"Bradd Pitt; you've been all your life in companion with beautiful women. Now you will be with this monstrosity for all eternity"
And the door closes as well, not to be open ever again.
Now it's only Tom
"Tom Green. Present at door 668" Tom goes to said door and enters. And what does he find? Demi Moore herself! Tom can't even believe it. And the voice speaks surprisingly: "Demi Moore, you've been all your life in companion with handsome men..."