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Footballguy
Because it's solitary, I gave some serious initial thought to a seasoned porn star's collection. But, I do think that would get old throughout the day and hopefully my memory of a past highlight reel would help there. So, in all seriousness, I do think I'd opt for non-porn.If I was in solitary confinement for a year- I think the emotion of laughter/humor would be very valuable to help cope. Thus, I’d want to pick someone that has a nice volume of hilarious stuff. Off the top of my head- people like Seth Macfarlane and Trey Parker come to mind.
I think the **** Wolf suggestion above as well as Steve Buscemi are really sneaky good selections because they give volume. Similarly, Conan O'Brien would give you his late show, podcasts, and The Simpsons. Some other good suggestions with Tarantino (though he wouldn't provide a series) and Joss Wheedon (series and movies). Tom Hanks provides range.
Gun to my head, though, I think I'd need to pour through IMDB and figure our some cross-sections to try to grab The Wire and some other really good series.
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