I got a kick out of this post from Gothamist, about an elderly lawyer who kept a notebook labeled “Tax Journal,” in which he dutifully recorded expenses that he later deducted. Good idea, in theory, but not when those supposedly tax-deductible expenses are, for 2002 alone, “$111,364 for ‘therapeutic sex’ and massages ‘to relieve osteoarthritis and enhance erectile function through frequent orgasm.'” The IRS declined to accept his visits to prostitutes, etc., as legitimate deductions, since they were illegal, AND he hadn’t saved the receipts.

The story reminded me of the mobster in the movie Casino who meticulously documented all his business expenses whenever he was sent across the country to help whack somebody, much to the enjoyment of the FBI!