“I Gotta Be Me”

By Eran Boodnero

Sammy Davis, Jr. was one of America’s greatest entertainers—and one of its most tragic.

At 3 years old, he started performing in his father’s vaudeville show. By 7, he was proficient in tap, trumpet, and comedy.

The group dealt with rampant racism—but Sammy’s father shielded him from its effects.

At 18, Sammy was drafted to fight in World War II. For the first time, he felt the full reality of racism. Fellow soldiers refused to sleep next to him, ordered him to polish their boots, and routinely beat him.

After the war, Sammy’s fame continued to rise—culminating in an invite to open for Frank Sinatra.

Success continued: chart-topping hits, Broadway leads, and Hollywood roles. Yet the same casinos that paid him millions barred him from sleeping in their hotels. Sammy wouldn’t stand for it, and he refused gigs until the casinos desegregated.

Fueled by a desire for justice, Sammy became a staunch supporter of civil rights— raising money for Martin Luther King Jr.’s work.

But his success carried a dark side. Sammy struggled with a lifelong battle of poor self-esteem and an insatiable desire to be liked. He turned to self-destructive behaviors—spending lavishly, infidelity, and eventually losing his marriage. His life spiraled into drugs, alcohol, and debt. By 1990, he owed 15 million dollars.

But he bounced back. After a tough conversation with Sinatra, Sammy quit drugs and returned to the stage.

Sammy’s life is a testament to the human spirit, struggle, failure, and success.

Timothy Sandefur will discuss “The Heartbreak and Heroism of Sammy Davis, Jr.” at LevelUp 2025. If you’d like to learn more about his amazing yet tragic life, then register now.

PS: Listen to Sammy’s song, “I Gotta Be Me”. It encapsulates his view of life beautifully, and it’s one of the most incredible songs I’ve ever heard.