The Custom Tokens
The first tokens for Hugh Hefner's Monopoly set were generalized representations of Playboy Bunnies. That changed in 1972, when Karen Christy, Playboy Playmate and Hefner’s girlfriend at the time, commissioned artist Tom Joris to create a more personalized set. Joris sculpted miniature likenesses of key figures in Hefner’s inner circle, including Shel Silverstein and film critic Gene Siskel. The results impressed Hefner so much that he expanded the project to include friends, associates, and his children. Over the next three years, he continued to commission additional tokens, gradually building a fully customized cast of Monopoly pieces. Each figure was individually crafted, making the set both intimate and distinctive. This transformation reflected not just Hefner’s lifestyle but also his desire to personalize the game with the people who surrounded him.
Tom Joris created three copies of each custom figure he sculpted for Hugh Hefner—one for the Chicago mansion, one for the Los Angeles mansion, and one for the Playboy Bunny Jet. Today, the whereabouts of many of these tokens remain unknown. The surviving set includes only one or two copies of certain figures, while others are missing entirely. This incomplete collection suggests that a more complete set may still exist, possibly in the possession of a family member or someone closely connected to the mansion.
Coming Soon: An Inteview with Jom Joris
Tokens Held – Identified
Hugh Hefner
As the founder and editor-in-chief of Playboy magazine, Hef was a cultural icon who redefined entertainment and lifestyle media in the 20th century. With a vision that blended sophisticated journalism, sexual liberation, and high style, Hefner built the Playboy brand into a global phenomenon and made the Playboy Mansion a legendary hub of celebrity, creativity, and conversation.
John Dante
Hugh Hefner’s close friend and considered by many the second in command of the Playboy empire, where he played a pivotal role in managing the behind-the-scenes operations of its famously lively social life. Often referred to as Hefner’s right-hand man during the Mansion’s heyday, Dante helped shape the atmosphere of elegance and excitement that defined Playboy’s golden era.
Victor Lownes
A key executive at Playboy and one of Hugh Hefner’s closest collaborators, instrumental in expanding the brand's reach during its early years. As the driving force behind the creation of the Playboy Club empire and Playboy’s UK operations, Lownes blended sharp business acumen with a flair for showmanship, helping to cement Playboy's international allure.
Shel Silverstein
A prolific writer, illustrator, and songwriter who contributed some of the most original and irreverent content to Playboy magazine during its formative years. A close friend of Hugh Hefner, Silverstein traveled the world on assignment for the magazine, producing witty, offbeat pieces that captured his singular voice — later echoed in his beloved children’s books like The Giving Tree and Where the Sidewalk Ends.
Gene Siskel
A renowned film critic who began his career as a writer for the Chicago Tribune and contributed film reviews to Playboy magazine during the 1970s. Best known for his long-running television partnership with Roger Ebert, Siskel brought sharp insight and a deep passion for cinema to his work, helping to elevate film criticism into mainstream cultural conversation.
David Hefner
Eldest son of Playboy founder Hugh Hefner with his first wife, Mildred Williams. Unlike his father, David has maintained a private life and pursued a career in film and media outside the spotlight of the Playboy enterprise.
Larry DuBois
A prolific Playboy interviewer and writer, best known for his in‑depth feature pieces during the 1970s. He authored a notable 1971 interview with director Roman Polanski, exploring the trauma of the Manson family murders. His work also included investigative reporting, such as the 1976 two‑part series “The Puppet and the Puppetmasters”, co‑authored with Lawrence Gonzales.
Shelley Carsten - Hugh's friend and personal accountant.
Lance Rentzel – Wide receiver for the Dallas Cowboys and Los Angeles Rams.
Played nine seasons in the NFL, notably for the Minnesota Vikings, Dallas Cowboys, and Los Angeles Rams. A standout at the University of Oklahoma, he led the Dallas Cowboys in receptions in 1967 and 1968, was selected to two Pro Bowls, and in 1969 topped the NFL in both receiving touchdowns and yards per catch.
Playboy Bunny – The most iconic symbol of the brand represented as a token.
Tokens Held – Unidentified
An unidentified token.
An unidentified token.
An unidentified token.
Missing Tokens
These tokens are known to have existed, but if any copies survive, their location is unknown.
Karen Christie - The originator of the token collection.
Bobbie Arnstein - Hugh Hefner's personal secretary
Barbi Benton - Singer and Entertainer. Hugh Hefner's long time girlfriend. (Photo provided by Tom Joris from his personal portfolio.)
Bill Cosby - Although no picture of the figure is available, a shipping receipt with a handwritten note from 1978 inbdicates that a Bill Cosby figure was sent from the Chicago Mansion to the Los Angeles Mansion.