Rich Uncle Pennybags
Rich Uncle Pennybags is the round old man with a mustachio in a top hat who serves as the mascot of the game Monopoly. In large parts of the world he is also, or even exclusively, known as Mr. Monopoly. He also appears in the related games Advance to Boardwalk, Free Parking, Don't Go to Jail, Monopoly City, Monopoly Junior, and Monopoly Deal.
The character first appeared on Chance and Community Chest cards in U.S. editions of Monopoly in 1936. The identity of the artist who designed the character has remained a mystery. 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 project manager for a carpet company. Orbanes later wrote, in 2006, that the character was also partially influenced by the stature and dress of financier and banker J. P. Morgan.
The unnamed character made his first appearance outside of Monopoly within the Parker Brothers' game Dig, released in 1940, before the U.S. entered World War II. The character did not receive a name until 1946 when the game Rich Uncle was published by Parker Brothers. His likeness appeared on that game's box lid, game instructions, and currency.
Between 1985 and 2008, the character appeared in the second "O" in the word Monopoly as part of the game's logo. More recently, the character is depicted over the word "Monopoly", drawn in a 3-D style, and extending his right hand. The character, however, no longer appears uniformly on every Monopoly game box.
In 1988, Orbanes published the first edition of his book The Monopoly Companion. In the book, all of the characters that appear on the Monopoly board or within the decks of cards received a name. Uncle Pennybags' full name was given as Milburn Pennybags, the character "In Jail" is named "Jake the Jailbird", and the police officer on Go to Jail is named "Officer Edgar Mallory".
In 1999, Rich Uncle Pennybags was renamed Mr. Monopoly. During the same year, a Monopoly Jr. CD-ROM game was released within cereal boxes as part of a General Mills promotion. This game introduced Mr. Monopoly's niece and nephew, Sandy and Andy.
According to the book, Monopoly: The World's Most Famous Game & How It Got That Way and The Monopoly Companion, Mr. Monopoly has a second nephew named Randy, although the Monopoly Companion mistakenly refers to Sandy as a boy. Monopoly: The World's Most Famous Game & How It Got That Way also states that Mr. Monopoly has a wife named Madge. He is named as the sixth richest fictional character in the 2006 Forbes Fictional 15 list on its website and the ninth richest in 2011.
Rich Uncle Pennybags has influenced or been parodied in popular culture. 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". An animated character resembling Rich Uncle Pennybags has appeared numerous times in The Simpsons, often alongside fellow plutocrat Montgomery Burns. These episodes include "Thirty Minutes over Tokyo," "A Hunka Hunka Burns in Love," and "The Seemingly Never-Ending Story." A 1986 Saturday Night Live sketch featured Jon Lovitz portraying Uncle Pennybags as a criminal lawyer who used his Get Out of Jail Free cards to constantly frustrate the police. Mr. Monopoly also appeared on two seasons of Family Game Night where he hands out Community Chest combination cards to the teams after each game. He also served as an inspiration for Vault Boy, the mascot of the Fallout series. 
- Hasbro Toy Shop page for Monopoly. The mascot character appears only on the Standard Edition set.
- USAopoly page for Monopoly. The mascot character appears on only about half of the editions shown.
- Orbanes, Philip (September 1999). The Monopoly Companion: The Player's Guide : The Game from A to Z, Winning Tips, Trivia. Adams Media Corporation. p. [page needed]. ISBN 978-1-58062-175-5. Retrieved 2009-06-26.
- Vanderkam, Laura (March 21, 2007). "Just Visiting". American.com. Retrieved 2009-06-26.
- "The Forbes Fictional 15 - #6 Mr. Monopoly". Forbes. 2006-11-20. Archived from the original on 2012-09-16. Retrieved 2009-06-26.
- "Tim Cain talk on FO3". 2002-03-09.
- "On Vault Boy and Pip Boy".
- Orbanes, Philip E. (2006). Monopoly: The World's Most Famous Game & How it Got that Way. Da Capo Press. ISBN 0-306-81489-7.
- Orbanes, Philip E. (2004). The Game Makers: The Story of Parker Brothers (First Edition ed.). Harvard Business School Press. ISBN 1-59139-269-1.
- Orbanes, Philip (1988). The Monopoly Companion (First edition ed.). Bob Adams, Inc. ISBN 1-55850-950-X.