Regina King — One Night in Miami

King won an Oscar for Best Supporting Actress (If Beale Street Could Talk, 2018), then immediately pivoted to directing One Night in Miami (2020) — a fictional meeting between Malcolm X, Muhammad Ali, Sam Cooke, and Jim Brown. It earned a 98% on Rotten Tomatoes and three Oscar nominations. She was the second Black woman to direct a live-action feature selected for the Venice Film Festival. King proved that the Oscar-winning actress could command a film about four of the most iconic Black men in American history, and every frame held up to that weight.