The face of Hef's custom Monopoly Money

The face of each bill features the visage of the man himself, with the banner OFFICIAL PLAYBOY CURRENCY above. A medallion bearing the Playboy Bunny logo appears on the left, while the one on the right combines a classic Monopoly house and locomotive - an homage to the original game. Denominations are printed in all four corners and below the central image.

Unlike classic monopoly money, Hef's custom money was also printed on the back. The reverse features two oval vignettes: the Chicago Playboy Mansion on the right and the Los Angeles Mansion on the left, each framed by ornate decorative filigree. Denominations are again positioned in all four corners for consistency and balance.

Monopoly games were played so frequently in the Mansion that the custom money had to be constantly replaced due to normal wear and tear. As a result, a substantial amount of reserve money was printed. Since Hefner's passing, many of these unused notes have entered the hands of collectors.

The face of Hef's custom Monopoly Money