Richie Rich

Released December 21, 1994, directed by Donald Petrie: Macaulay Culkin starred as Richie Rich, the world's richest boy. The character itself had roots deeper than the film—Richie Rich debuted in Harvey Comics' Little Dot #1, cover-dated September 1953, and went on to star in his own series from 1960 to 1991, running 254 issues. In the film, Richie lived in a mansion of impossible excess: a McDonald's inside the house, Professor Keenbean's gadget laboratory, and a family vault hidden behind "Mount Richmore," a mountainside carved with the family's portraits. John Larroquette played the villain Laurence Van Dough; Jonathan Hyde was the butler Cadbury.

The film's budget was a lavish $40 million, but it returned only $38 million domestically and roughly $76 million worldwide—a soft box-office result that suggested the fantasy of unlimited childhood wealth had limits. Critics were unkind, but the film found its audience among children for whom the premise—a kid with every toy, unlimited resources, zero parental supervision—was the platonic ideal of freedom.

This was Macaulay Culkin's last film before he walked away from acting. Tired of acting and hungry for a normal childhood, he enrolled in a private Manhattan high school, away from sets and scripts. He wouldn't return to acting until around 2000, when he appeared in the London stage production of "Madame Melville"—but by then, Richie Rich had already cemented its place in the mythology of 90s kid culture: everything money could buy, and nobody telling you no.