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In 1993, De Niro made his directorial debut with A Bronx Tale. The film, written by Chazz Palminteri, was about Palminteri's turbulent childhood in the Bronx. De Niro agreed to direct the film after seeing Palminteri's one-man off-Broadway play. De Niro also played Lorenzo, the bus driver who struggles to keep his son away from local mobster Sonny, played by Palminteri.

De Niro hadn't directed another film until 2006's The Good Shepherd, which starred Matt Damon and Angelina Jolie. The Good Shepherd depicts the origins of the CIA, with Damon portraying one of the top counter-intelligence agents during World War II and the Cold War. De Niro has a small role as General Bill Donovan, who recruits Damon's character into the world of counter-intelligence.

A major plotpoint in each De Niro-helmed film invloves a contentious interracial relationship: between Italian Calogero and African-American Jane in A Bronx Tale, and WASP Edward Jr and Congolese Miriam in The Good Shepherd. De Niro himself has been romantically linked to several women of African descent.
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