This theoretical stuff is funny but I think I've been inspired to go and create Charlie Sheen for Fallout: New Vegas.
High luck/endurance/charisma low endurance/strength/perception and average intelligence.
Lady Killer Perk, Chem Resistant Perk, (Mysterious Stranger?)
Companion = Rose Sharon of Cassidy
Consume bottle of alcohol after each load screen, three after resting.
Consume every stim I find, buy more from Dixon when getting the shakes.
Brief stint of rehab working with Followers, make friends with Arcade.
Alienate Arcade with foolish decisions, go back to Cass, hit Cass, travel with Veronica/Rex.
Ending... either independent by mistake (too drunk to complete either sides tasks) or Mr. House since he provides a place to get loaded and lots of caps.
Lose all money in a casino every few game days.
What I can't decide is the weapons, Charlie Sheen seems like he'd be a punch you kind of guy but with low strength he won't do well unless I can get tons of buffout/psycho. Maybe a pistols kind of guy? I guess he carried some heavier weapons in Hot Shots part Deux... hmmm.