Willie Nelson (26/30)

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After leaving high school in 1950, Willie Nelson joined the Air Force. However, he was discharged nine months later due to suffering back problems. And while he worked a string of odd jobs and moved frequently, he started his music career at the same time. It only took 20 years to achieve success, but he still credits his time in the military for giving him the structure and perseverance needed to make it as an American Country icon.