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Well remember that copyright/trademark infringement only happens when the goal is misleading or a "reasonable person" could get confused.
eg Howard Stern's book Miss America was declared not to be a copyright infringement because any reasonable person would not think the book was about the Miss America Pagent.
So you could make a site with the word Playboy in it so long as a reasonable person wouldn't think it was from THE Playboy. You'd probably still get sued, but you might win.
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