Willie Nelson – U.S. Air Force

Who doesn’t know Willie Nelson, one of the most recognized country music singers with his signature hippie look? In his youth, Willie did all sorts of jobs to support himself, including being a pawn shop employee or a tree trimmer. Nelson left school and joined the United States Air Force in 1950. He served between eight and nine months. Nelson later became one of the leading figures of outlaw country and gained huge success. However, he had his fair share of troubles in 1990 when the IRS seized his assets and he was in dire need of a debt relief. He released two studio albums in 2018: Last Man Standing and My Way.