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Contino studied accordion primarily with San Francisco-based Angelo Cognazzo, and occasionally with Los Angeles-based Guido Deiro. Early on he exhibited great virtuosity on the instrument. Although he graduated from Fresno High School in 1947 and enrolled at Fresno State College, he was unable to concentrate on his studies. Contino explained, "I enjoyed college, but while attending classes I kept thinking that if I was going to be a success, it would be my music that would take me there." 
Contino got his big break on December 7, 1947 when he played Lady of Spain (his signature piece) and won first place in the Horace Heidt/Philip Morris talent contest in Fresno which was broadcast on national radio. Contino also won first place in subsequent competitions in Los Angeles, Omaha, Des Moines, Youngstown, Cleveland, Pittsburgh, Harrisburg, and New York City. He won first place in the final round on December 12, 1948 in Washington, D.C. Eddie Fisher had much better success with the song in 1952. Contino's song "Yours" was his first hit single. The song reached #27 on the U.S. pop charts in 1954. His second and only other hit single was "Pledge My Love." It reached #42 on the U.S. pop charts in 1957.
Contino toured with the Horace Heidt Orchestra and was billed as the "world's greatest accordion player." He appeared on The Ed Sullivan Show a record 48 times.
However, his success was interrupted when Contino was drafted during the Korean War. Contino, at the time earning a reported $4,000 per week, fled from pre-induction barracks at Fort Ord, due to extreme and unpublicized phobias and neuroses.  He was falsely labeled a 'draft dodger' and was jailed for a few months before proudly serving in the United States armed forces and being honorably discharged as a Staff Sergeant and receiving a Presidential Pardon. The resultant scandal dealt Contino's career a serious blow, but he continued performing, including acting in a few movies in the 1950s and 1960s.
Contino's acting became known to a new generation in 1991, when "Daddy-O," a low-budget 1958 movie in which he played the starring role as a faddishly-dressed beat rebel and singer, became the centerpiece of an episode of the third season of "Mystery Science Theatre 3000."
Contino continues to perform regularly throughout the United States. His repertoire is eclectic, ranging from Italian songs such as "Come Back to Sorrento" and "Arrivederci Roma" to standards like "Lady of Spain" and "Swinging on a Star." He possesses a virtuosic technique (often incorporating extremely rapid fingering, glissandos, and bellows shakes) and is also a skilled jazz improvisor.
James Ellroy wrote a novella, Dick Contino's Blues, which is a mini-memoir and crime story based on Contino's experiences as a struggling artist after the war. It is included in the 1994 Ellroy short story collection Hollywood Nocturnes. A version appeared in issue number 46 of Granta magazine (Winter 1994) along with several photographs of Contino and the author. Ellroy also penned a short story entitled Hollywood Shakedown which appeared in his collected work "Crime Wave" and featured Contino as the central character. The story is entirely fictitious as it features numerous incidents of violence and murder which Contino had never been linked with or accused of in reality.