Dean Martin's classic croon projected the kind of warm confidence that you'd expect from a founder of the Rat Pack. In the '50s, the Ohio-born Italian-American became a huge star thanks to the tunes he chose to record—classically poignant and witty gems of regret, romance, and yearning. He was, among many other things, a master interpreter of songs. His influences ranged from big band swing to opera to country music, and in 1964 he was still the ultimate king of martini cool, knocking The Beatles off the top of the singles chart. His star ascended into TV, stage, and film, and he died in 1995 a cultural legend.