Frank Sinatra Photography

Frank Sinatra

No one interpreted the “Great American Songbook” like Frank Sinatra, which is probably why his 150 million album-selling career is still being celebrated. Originally a swing singer with Harry James and Tommy Dorsey, “Ol’ Blue Eyes” went solo in 1946 and rode the roller coaster of musical strides and personal setbacks well into the ’90s.

Though it is impossible to succinctly condense Sinatra’s greatest works, some of his countless crests include the standards “The Way You Look Tonight,” “Fly Me to the Moon,” and “My Way.” Along the way, the “Chairman of the Board” and leader of the “Rat Pack” became staples of both Las Vegas showrooms and the Hollywood screen, logging classics like From Here to Eternity, Guys and Dolls, and Ocean’s 11.

In his elder years, Sinatra attracted the ears of an entirely new generation thanks to two Duets projects that found him singing alongside everyone from Bono to Tony Bennett. And though the world lost this legend in 1998 at 82, the reissues, documentaries and tribute shows continue at such a rapid rate that it barely seems like he’s gone.

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