Kirk Cameron.
I win.
Depending on what this response means, perhaps “you’re going to hell” isn’t a completely hypothetical premise.
In the movie “Little Nicky”, Hitler is shown being forced to wear a french maid outfit and is brought into Satan’s Office once a day to have a pineapple shoved up his ass.
But do really want them after he’s done with them?
I want to bunk with Adriana Lima. Oh yes, mmm…
I’ll settle for Laurie Dhue, thank you. 
If Marilyn Monroe is not available, I’ll take Thomas Jefferson. Either way, there will be lots to pass the hours with.
Oscar Wilde!
Hunter Thompson in his prime. 
(Meaning, I want to bunk with someone I can still screw. haha.)
Oh, and Johnny Knoxville. I have an unholy crush on the Jackass.
Sean Young.
I wouldn’t mind living next door to Hunter S Thompson or maybe across the street from him. But for a roommate, I’m an old fashioned type of guy so I would like to have the second season Charlie’s Angels.
I think it’s funny we assume that these people are going to or are in hell, providing there actually is a hell. Very few of them are guilty of more than a little indulgence.
Well, according to Homer Simpson, Abraham Lincoln sold poisoned milk to schoolchildren.
But out of at least two President that can be confirmed from the Simpsons, I’m going to have to go with JFK.
Waitaminnit, I thought an indulgence got you off the hook! I’m so confused…
The Devil is known (by those who profess to both know him and yet not be bound to him :rolleyes: ) to be a tricky SOB. I fear that if I picked, say, Naomi Watts I’d get her as a roomie and would have to endure being in her presence for an eternity without ever getting a piece. No good.
But since Hell is all about suffering, I think I’d rather rely on my own skills at making others suffer, that way The Devil gets good use of me, and I make a proactive use of my time. Therefore I’d select someone who is demonstrated to be thoughtful, intelligent, witty and well-published–whose better thoughts are easily perused over the internet. Someone who received at least some respect for who and what he was in life but, by virtue of his non-belief in redemption, is hell-bound.
I pick…Lobsang.
<gulp> Are you sure that’s me, and not some other ‘Lobsang’ you’re talking about?
A lotta compliment for one heart. You tryin to hasten my journey deepwards?
My problem is that I’m mildly paranoid, so I’m sure that if I got a cool roommate for eternity I’d worry that I was their personal hell.
Also, as a wise man once said, “Somewhere out there is a guy who is sick of Cindy Crawford’s shit”.
I want two roommates:
Antonio Banderas, to make Hell seem like Heaven.
Fred Phelps, to make sure he gets the Hell he deserves.
Since he’d probably go to Hell for all the nude scenes and racey films he’s done, Ewan McGregor, without a doubt.
Colette
Cleopatra, or maybe Bodacea.
…Which, y’know, knowing my luck, would mean that their eternal punishment would be to messily disembowel their roomate with their teeth for eternity. :smack:
Teller, from Penn and Teller. He seems like the quiet type.
Marcel Marceau might be quieter, but I don’t want to make hell any worse than it has to be.
Of course my real choice would be some hot female sinner, but I’m not sure which hot women are definitely going to hell.