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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 " and " A Hunka Hunka Burns in Love ".

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.