On This Day 28 Years Ago, We Said Goodbye to the “Chairman of the Board”, One of the Most Beloved Entertainers of All Time

More than a decade before Elvis Presley performed for swooning crowds, another artist commanded that same level of adoration. Widely regarded among the best singers of all time, Frank Sinatra elevated pop music to an art. But his impact reached far beyond the music industry, with a resume that included both Grammys and an Academy Award. On this day (May 14) in 1998, Sinatra died from a heart attack at Cedars-Sinai Medical Center in Los Angeles. He was 82 years old.

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The “My Way” crooner’s daughter, singer Nancy Sinatra, took to Instagram to remember “one of the most extraordinary men” she’d ever known.

“Twenty-eight years later, the world still sings along with him,” wrote the “These Boots Are Made For Walking” singer, 85. “Young people continue discovering him for the first time, while those who loved him from the beginning still treasure the man and his music. His music is special because it came from somewhere real, and because he meant every word he sang.”

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Frank Sinatra: One of the All-Time Greats

The only child of Italian immigrants, Francis Albert “Frank” Sinatra was born on December 12, 1915, in Hoboken, New Jersey.

Idolizing artists like Bing Crosby, Gene Austin, Russ Colombo, and Bob Eberly, Sinatra grew up singing for spare change at the tavern his parents owned in town.

“General rowdiness” led to his expulsion from high school, and he began performing at Hoboken social clubs and singing for free on local radio stations.

Never learning to read music, Sinatra’s break nonetheless came in 1935 when his mother persuaded local singing group the 3 Flashes to let him join. As the “Hoboken Four,” they auditioned for the Major Bowes Amateur Hour, landing a six-month contract to perform across the U.S.

Sinatra quickly became the group’s lead singer—and the object of most female admiration, much to his bandmates’ chagrin. Four years later, he cut his first record, “From the Bottom of My Heart”, with trumpeter and bandleader Harry James.

The record sold no more than 8,000 copies, and Sinatra’s following records didn’t fare much better commercially. Frustrated with the lack of traction, he left James’ band in November 1939 to join the Tommy Dorsey Band as lead singer.

[RELATED: 3 Times Frank Sinatra Graced Rock Songs With His Classy Vocals]

Evolving With the Times

With a career spanning five decades, Frank Sinatra became a master of reinvention. He began his time in music as the starry-eyed idol of the “bobby soxers,” scoring hits like “I’ll Never Smile Again” (1940) and “All or Nothing at All”.

Post-World War II, something hardened in the American psyche, and Sinatra’s appeal began to fade. Undaunted, he mounted a comeback as a more rough-and-tumble, jaded crooner.

Earning 11 Grammy Awards, Sinatra is among the world’s most commercially successful musical artists, selling roughly 150 million records. He also embarked on a flourishing acting career, winning the Academy Award for Best Supporting Actor for his role inthe 1953 war drama From Here to Eternity.

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