The Custom Tokens
The game tokens in Hefner's Monopoly set were mini sculptures—custom cast and hand-finished to represent people, objects, and symbols important to Hefner’s world. Each piece was a detailed work of art.
Notable tokens included a typewriter, a Playboy Bunny logo, a smoking jacket on a hanger, and even a mini cocktail glass. These tokens were designed and produced by professional model makers in the early 1970s, likely through Hefner’s connections in the entertainment and publishing industries. Each was unique and tailored to reflect his lifestyle and brand.
Tokens – Included – Identified
John Dante – Longtime friend and associate known for his work with Hefner in club operations.
David – Identity under research, but likely a staff member or close friend of Hefner.
Larry DuBois – A close friend and associate, captured in a miniature likeness.
Victor Lownes – Playboy executive in the UK; depicted in this detailed figure.
Shel Silverstein – The beloved poet and Playboy contributor represented here.
Shelly – A friend or staffer token, identity confirmed through 1970s imagery.
Gene Siskel – Film critic and regular Mansion guest; captured in miniature.
Playboy Bunny – The most iconic symbol of the brand represented as a token.
Hugh Hefner – The man himself, rendered in token form as a tribute within the game.
Tokens – Included – Unidentified
Unlabeled object resembling an abstract sculpture.
Tokens – Missing
Original pipe token — last seen in 1974 photographs but not present in surviving sets.
