On This Day in 1998, Entertainment Royalty Gathered To Say Goodbye to Music’s Greatest Crooner

Frank Sinatra was a once-in-a-generation star. He was the epitome of cool in his day, balancing era-defining songs, movie stardom, and unmatched cultural cachet. There was no one like him before, and no one has come around to challenge his singular popularity since his death in 1998. On this day of that year, entertainment royalty gathered to bid “Ol’ Blue Eyes” goodbye in Beverly Hills.

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Frank Sinatra: The Singer

Before his death, Sinatra built one of the most illustrious careers of all time. From local singing groups in New Jersey to the silver screen, Sinatra’s star shot up in a straight line.

He was officially discovered in 1939 while working as a waiter at the Rustin Cabin in New Jersey. Harry James, of the Benny Goodman orchestra, found this unmatched talent and added him to his new solo venture. He was later released from his contract with James to join the Tommy Dorsey band, earning his first major breakthrough.

Soon thereafter, Sinatra’s talent was undeniable, leading him to venture out on his own. A bitter fight with Dorsey ensued, but the crooner broke free. His solo success was almost immediate. The “bobby-soxers” of the world were in frenzy when Sinatra came around, earning a type of fame that few of his peers could boast.

Sinatra’s seemingly unstoppable star only hit a snag when his connection to organized crime members came out in the late 40s. He experienced a career decline that no one could’ve seen coming. But that decline was quickly turned on its head with the release of Come Fly With Me. This album, as well as his other late 50s work, is considered his best. Sinatra managed to turn a bad situation around, becoming one of the most beloved crooners of all time.

Frank Sinatra: The Movie Star

Another pivotal vehicle in getting Sinatra back on top was his many films. Seldom has a singer been just as well known for acting as Sinatra was. His turn into acting is what first helped him get back on top after his period of decline.

His most famous film appearances include the musical comedy, On The Town, From Here to Eternity, The Manchurian Candidate, and the original version of Ocean’s 11. Sinatra proved the diversity of his talent through these films, helping him get back to the top of the music world as well.

The Crooner’s Funeral

Given how pivotal Sinatra was to the entertainment industry, it should come as no surprise that his funeral was a list of “who’s who.” Held at the Church of the Good Shepherd in Beverly Hills, the service drew mourners including Tony Bennett, Jack Nicholson, Sophia Loren, and Kirk Douglas.

One of the more peculiar aspects of the service was what was placed in the casket with the crooner. The list included Tootsie Rolls, cherry Life Savers, Camel cigarettes, a Zippo lighter, Jack Daniel’s whiskey, and a roll of 10 dimes.

The 10 dimes come from a comfort thing Sinatra upheld throughout much of his life. After the kidnapping of his son in the 1960s, Sinatra had to communicate with the perpetrator through payphones. On one phone call, Sinatra ran out of change. From that point on, the musician always carried coins with him wherever he went. Natrually, his children saw to it that he be buried with change as well.

Sinatra’s funeral wasn’t just about mourning a singular man, but about an icon who represented a bygone era in entertainment history. His fellow musicians and actors came out in support both as friends and as peers. The death of Sinatra marked much more than the end of his life. It was the end of crooner history as we knew it.

(Photo by Graphic House/Archive Photos/Getty Images)