According to 'Barry Levinson', this film came out of a derogatory comment about Dustin Hoffman's character in Sphere (1998). The critic's comment got Levinson thinking about his experiences growing up in Baltimore, and Liberty Heights was born.
Director Barry Levinson wanted someone with a Grace Kelly appeal to play the role of Dubbie the Blonde. Model Carolyn Murphy was cast, although she was ironically dubbed "The Blond Haired Gene Tierney" by Elle. She auditioned for the role after her agent encouraged her to do so, and unlike many other models turned actresses, she was praised for her work.
In the scene where they are teeing off at the 'golf course', they are actually standing on the lawn in front of the Mansion House in Baltimore's Druid Hill Park. The Mansion House is the current day administrative offices for the Baltimore Zoo. There is no real golf course in Druid Hill Park.