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Van Dyke left high school in 1944, his senior year, intending to join the United States Army Air Forces for pilot training during World War II. Denied enlistment several times for being underweight, he was eventually accepted for service as a radio announcer before transferring to the Special Services and entertaining troops in the continental United States.[11] He received his high school diploma in 2004 at the age of 78.[12]

In November 1959, Van Dyke made his Broadway debut in The Girls Against the Boys. He then played the lead role of Albert Peterson in Bye Bye Birdie, which ran from April 14, 1960, to October 7, 1961. In a May 2011 interview with Rachael Ray, Van Dyke said that when he auditioned for a smaller part in the show he had no experience as a dancer, and that after he sang his audition song he did an impromptu soft-shoe out of sheer nervousness. Gower Champion, the show's director and choreographer, was watching, and promptly went up on stage to inform Van Dyke he had the lead. An astonished Van Dyke protested that he could not dance, to which Champion replied: "We'll teach you". That musical won four Tony awards including Van Dyke's Best Featured Actor Tony, in 1961.[16] In 1980, Van Dyke appeared as the title role in the first Broadway revival of The Music Man.[17]
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