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At the age of 15, he was a boxer who billed himself as "Kid Crochet". His prizefighting years earned him a broken nose (later straightened), a scarred lip, and many sets of broken knuckles (a result of not being able to afford the tape used to wrap boxers' hands). Of his twelve bouts, he would later say "I won all but eleven." For a time, he roomed with Sonny King, who, like Martin, was just starting in show business and had little money. It is said that Dean Martin and King held bare-knuckle matches in their apartment, fighting until one of them was knocked out; people paid to watch.
Eventually, Martin gave up boxing. He worked as a roulette stickman and croupier in an illegal casino behind a tobacco shop where he had started as a stock boy. At the same time, he sang with local bands. Calling himself "Dino Martini" (after the then-famous Metropolitan Opera tenor, Nino Martini), he got his first break working for the Ernie McKay Orchestra. He sang in a crooning style influenced by Harry Mills (of the Mills Brothers), among others. At his EARLY LIFE, he started singing for bandleader Sammy Watkins, who suggested he change his name to Dean Martin.
In October 1941, Martin married Elizabeth Anne McDonald. During their marriage (ended by divorce in 1949), they had four children. Martin worked for various bands throughout the early 1940s, mostly on looks and personality until he developed his own singing style. Martin famously flopped at the Riobamba, a high class nightclub in New York, when he succeeded Frank Sinatra in 1943, but it was the setting for their meeting.
Martin repeatedly sold 10 percent shares of his earnings for up front cash. He apparently did this so often that he found he had sold over 100 percent of his income. Such was his charm that most of his lenders forgave his debts and remained friends.
Drafted into the United States Army in 1944 during World War II, Martin served a year stationed in Akron, Ohio. He was then reclassified as 4-F (possibly due to a double hernia; Jerry Lewis referred to the surgery Martin needed for this in his autobiography) and was discharged.
By 1946, Martin was doing relatively well, but was still little more than an East Coast nightclub singer with a common style, similar to that of Bing Crosby. He drew audiences to the clubs he played, but he inspired none of the fanatic popularity enjoyed by Sinatra.