This is a creepy question, but I can go with it. Garry Shandling. I get the sense he has lots of cool celebrity friends, and I remember seeing him on 2 shows on HBO where he was making side comments to fellow guests that no one else could hear that was cracking them up, so guessing his humor extends to stuff like personal emails.
I'd go with Sheen. That dude is into some really fucked up shit. It'd be like a male version of "50 Shades"
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