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In the early- to mid-1960s, Dean Martin emerged as one of the most popular entertainers on the planet, starring in major films, knocking the Beatles off the top of the charts with what would become his trademark tune, “Everybody Loves Somebody,” defining an entire new genre of cool with Sinatra and the rest of the Rat Pack, starring in his own long-running TV variety show — achieving all of this with the air of a man who had just woken from a nap and was still charmingly groggy.
In 1958, meanwhile, when the pictures in this gallery were made, Dino — while famous as one-half of the Martin & Lewis comedy duo — had not yet crossed over into genuine superstardom. But he was certainly enough of a draw that LIFE magazine devoted a photo-filled seven-page feature to the man they dubbed “Make-a-Million Martin.”
On what would have been his 97th birthday (b. June 7, 1917, in Steubenville, Ohio) LIFE pays tribute to one of show business’ enduring — and most laid-back — legends.