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Remember those lazy, hazy, crazy days of summer with the top down—or at least the windows open — and Top 40 blasting from the radio.

Frank Sinatra would have turned 100 on Dec. 12 of this year, but even if you played three of his recordings every day from now till then, you wouldn’t come close to exhausting his songbook: The best estimates suggest the Chairman of the Board recorded about 1,000 different songs in the studio.