Guess which item brought in the most dough....
The Underwood Standard Portable typewriter is the one he used to write articles for the first issue of the magazine in 1953. It was purhased for $162,500! Hefner's copy of that issue, which featured nude pics of Marilyn Monroe, sold for $31,250.
One of Hefners trademark red silk smoking jackets sold for $41,600. And a gold and onyx ring with a compartment in which he kept a Viagra pill was purchased for $22,400.