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Brewster’s Millions (1985)

After losing his position as a minor-league pitcher, Montgomery Brewster (Richard Pryor) learns his great-uncle has left him $300 million. To inherit it, Brewster must spend $30 million in 30 days under a complicated set of rules that forbid him from donating too much to charity or retaining any new assets when the period is up. Unable to share details about the will’s odd conditions with anyone, Brewster sets out to spend his money under the stern eye of paralegal Angela Drake (Lonette McKee).

Clueless (1995)

Shallow, rich and socially successful Cher (Alicia Silverstone) is at the top of her Beverly Hills high school’s pecking scale. Seeing herself as a matchmaker, Cher first coaxes two teachers into dating each other. Emboldened by her success, she decides to give hopelessly klutzy new student Tai (Brittany Murphy) a makeover. When Tai becomes more popular than she is, Cher realizes that her disapproving ex-stepbrother (Paul Rudd) was right about how misguided she was — and falls for him.