Francis Albert Sinatra (1915–1998) was born on this day in Hoboken, New Jersey. Regarded by friends as generous and loyal, he carried a unique blend of power and talent that shaped twentieth-century music.

“Whatever else has been said about me personally is unimportant. When I sing, I believe I am honest,” Sinatra once said. That belief in emotional truth stayed at the center of his work.

Inspired by his hero Bing Crosby, Ol’ Blue Eyes cut his first record in 1939. A year later the skinny kid was singing romantic ballads with the Tommy Dorsey Band and sending bobby-soxers into a frenzy. His phrasing felt conversational and close, a voice that carried both vulnerability and confidence.

“By infusing lyrics with a personal, intimate point of view,” eulogized the New York Times, “he conveyed a steady current of eroticism.” In 1999, Time magazine described Sinatra as “a jazz-influenced singer” whose performances held “the sheer force of conviction, feeling, the weight of personal history in his voice.”

His recordings were many and cherished: Witchcraft, Young at Heart, Strangers in the Night, and That’s Life. He is most closely linked with My Way, written for him by Paul Anka, a song that reflects his honesty and fierce passion for living on his own terms. “It’s Frank’s world,” said fellow Rat Packer Dean Martin, “We’re just lucky to be living in it.”

U2 frontman Bono presented Sinatra with a 1994 Lifetime Achievement Grammy and saluted him as “a man heavier than the Empire State, more connected than the Twin Towers, as recognizable as the Statue of Liberty, and living proof that God is a Catholic.”

A humanitarian and an icon with “swagger and attitude,” Sinatra acted in more than fifty films and won a Best Supporting Actor Oscar for his role in From Here to Eternity alongside Burt Lancaster. To many, he remains the most influential entertainer of the twentieth century.

Singer Tony Bennett remembered, “One of Sinatra’s favorite toasts to make with a glass in hand was, ‘May you live to be 100 and may the last voice you hear be mine.’” The master is gone, yet his voice still fills rooms, reminding listeners of what a single song can hold.