The movies Ace Ventura: When Nature Calls and Mr. Deeds featured characters who resemble Rich Uncle Pennybags, prompting the main characters to refer to each of them as "The Monopoly Guy".
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Orbanes later wrote, in 2006, that the character was also partially influenced by the stature and dress of financier and banker J. P. Morgan.
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Historian and author Philip Orbanes wrote in 2004 that it is believed that the character is based on either the calling cards of Albert Edward Richardson (Parker Brothers' first traveling salesman), the character of "Little Esky" from Esquire magazine, or a combination of the two.
Uncle Tom's Cabin | Buddy Rich | Uncle Sam | The Rich Pay Late | Uncle Vanya | Uncle Tupelo | Charlie Rich | Uncle Remus | Frank Rich | Robert Rich | Robert Rich (musician) | Get Rich or Die Tryin' | Big & Rich | Uncle Dave Macon | Rich Mullins | Rich Man, Poor Man | Rich Little | Rich Fulcher | Get Rich or Die Tryin' (film) | Charles C. Rich | Sharon Rich | Rich Porter | Rich McKay | Rich Franklin | Lifestyles of the Rich and Famous | Uncle Tom | Uncle Scrooge | Uncle Fester | Rich Lowry | Rich in Love |