Innovative jazz singer and bandleader William Clarence Eckstein (1914–1993) was born on this day in Pittsburgh, Pennsylvania. With a passion for both football and music, he entered his first singing contest at age seven.

“If you want to be a doctor, a lawyer, you must go to college. But if you want to be a musician or such, study your craft. Study music,” he once said.

In 1939, Eckstine—known as “Mr. B”—sang and played trumpet with the Earl “Fatha” Hines band, collaborating with legends like Dizzy Gillespie, Sarah Vaughan, and Charlie Parker. He delivered the unforgettable Jelly, Jelly and honed his skills by continually learning new licks.

By 1944, he formed his own groundbreaking bebop band—a celebration of jazz and swing. “I like a song that tells a story and has some meat to it, you know, that means something,” he said.

His velvety bass-baritone voice rivaled Frank Sinatra with hits like That Old Black Magic, I Apologize, and I Wanna Be Loved. He created mainstream success with elegance and depth.

Biographer Will Friedwald called Billy’s voice a “blue dream... so unendingly beautiful, rich and full, that one has a hard time believing that something so perfect can exist in the natural world.”

His vibrato touched the heart, and his fashion—loose collars, narrow ties, flowing jackets—dazzled the fashion world. “You can't sing about love unless you know about it,” he said.

A man of deep convictions and elegance, Eckstine broke barriers not just musically, but culturally.