Born Dino Paul Crocetti in Steubenville, Ohio to an Italian immigrant father and Italian-American mother, Dean Martin went from high school dropout to one of the entertainment industry’s most popular, versatile, and award-winning singers and actors, earning the nickname, “The King of Cool.”

Martin left school at 15 and donned boxing gloves, fighting as a welterweight. He recalled his boxing “career” with his trademark wit, saying that out of his 12 matches, he “won all but 11.” After hanging up the gloves, he earned money dealing poker and blackjack at local speakeasies. After hours, he hit the club scene, singing in the style of the great crooner, Bing Crosby, until eventually finding his own distinct “voice.”

In 1946 Martin was singing at a New York hotel, where a young comic named Jerry Lewis was also performing. The two became fast friends. When they combined their respective acts, Martin playing the debonair singer to Lewis’ goofball clown, their popularity soared and led them straight to Hollywood. Lewis and Martin made 16 movies together including My Friend Irma, The Stooge, and Hollywood or Bust, their final film before the duo split.

After a rough start, Martin’s solo career as an actor and a singer took off. His hits included the gold records, That’s Amore, Return to Me, Volare, and Everybody Loves Somebody, the iconic theme song of his multi-award-winning variety show, The Dean Martin Show. In 1964, at the height of Beatlemania, the song knocked the Fab Four’s A Hard Day’s Night off the top of the Billboard Hot 100 chart.

Martin was best known for his comedy films with Jerry Lewis but, after going out on his own, he branched out to more dramatic roles, including the Westerns Rio Bravo (1959), in which he sang a duet with Ricky Nelson, and The Sons of Katie Elder (1965)—both with John Wayne—plus Rough Night in Jericho (1967) with Jean Simmons, George Peppard, John McIntire, and Slim Pickens, and Bandolero (1968) with Jimmy Stewart and Raquel Welch.

He started hanging out, golfing, and performing in Las Vegas with Hollywood’s legendary Rat Pack—made up of Frank Sinatra, Sammy Davis, Jr., Joey Bishop, Peter Lawford, Sammy Cahn, and sometimes, Ruta Lee, and Shirley MacLaine—among the few women who could hold their own trading bawdy barbs with the boys! Martin became known as the Chief Deputy to the Chairman of the Board—Frank Sinatra. In all, Martin made more than 50 films during his four-decade career. One of the most popular, the iconic heist film, Ocean’s Eleven, starring Martin, and all his Rat Pack compadres, along with Angie Dickinson, herself one of the rare Rat Pack gals. Other notable films on Martin’s lengthy résumé include Some Came Running (1958), Robin and the Seven Hoods (1964), Airport(1970), and Cannonball Run (1981).

In 1987, Martin’s son—former actor and singer, Dino Martin, Jr., member of the 1960s pop band, Dino, Desi (Desi Arnaz, Jr.) and Billy—died in a plane crash while serving as a pilot in the California Air National Guard. Dean Martin never recovered from the loss and retreated from the limelight. Dean Martin died from lung cancer at age 78 on Christmas Day, 1995.

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