Paper Moon (1973)

Directed by the exceptional Peter Bogdanovich, this classic road comedy-drama follows Moses, a charismatic conman played by Ryan O'Neal, and Addie, a clever young girl, as they navigate through America engaging in clever scams to raise money during the Great Depression. Portrayed with exceptional chemistry by the real-life father-daughter duo, this black-and-white masterpiece earned Tatum O'Neal the Academy Award for Best Supporting Actress, making her the youngest winner in the history of the Oscars.