well, first choice would be the good Dr. of gonzo, H.S. Thompson....though smoking wouldnt be my first choice for hanging with him, but would be included...
alive, would be Johnny Depp, as he was the person to take a friendship with thompson, and then was the person to respect his final wishes, no matter how ludacris they seemed to other people..... and his actor persona has seemed to change a good bit since then.....
After that, would have to be good 'ole "Honest Abe"..... cant really explain why, but I've had an odd connection with him since an early teen acid trip........ I got him then