Kris Kristofferson – U.S. Army

Kris Kristofferson became a notable name in the music industry in the 1970s. He is well-remembered for his songs like Me and Bobby McGee, Help Me Make It Through the Night, and Sunday Mornin’ Comin’ Down. Because his family really wanted it for him, Kris joined the U.S. Army. He worked hard and eventually took on the role of a captain. During the time that he wasn’t successful in music yet, he struggled to pay for his son’s medical bills and we’re sure he wished he had invested in health insurance.