Rich Uncle Pennybags aka Mr. Monopoly is a fictious character from the classic board game Monopoly made by the parker brother.

Rich Uncle Pennybags aka Mr. Monopoly is the funny old guy smoking cigars that represent the game monopoly made by parker brother. Rich Uncle Pennybags is the rotund old man in a top hat who serves as the mascot of the game Monopoly. He also appears in the related games Advance to Boardwalk, Free Parking, Don't Go To Jail, and Monopoly Junior. Rich Uncle Pennybags was rechristened Mr. Monopoly (a nickname he was already known by in popular culture) in a Hasbro marketing effort in 1999.

Monopoly board. The character first appeared on Chance and Community Chest cards in U.S. editions of Monopoly in 1936. The artist who designed the character to appear across several of the cards 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 Richardson (Parker Brothers' first traveling salesman) or the character of "Little Esky" from Esquire magazine or a combination of the two. 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 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.

Since 1985, the character appears in the second "O" in the word Monopoly as part of the game's logo. While this logo has generally been adopted worldwide, the character still only appears on Chance and Community Chest cards on U.S. versions, though not in certain themed releases.

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's full name was given as Milburn Pennybags, the character "In Jail" is named "Jake the Jailbird," and the police officer in the opposite corner to the jail is named "Officer Edgar Mallory."

In 1999, The same year Rich Uncle Pennybags was renamed Mr. Monopoly, a Monopoly Jr. CD-rom game released within cereal boxes as part of a General Mills promotion, Sandy and her brother Andy, Mr. Monopoly's niece and nephew, were introduced.