#5: Willie Nelson
Rank: Airman Basic, United States Air Force
Duration: 9 Months
Upon graduating high school in 1950, country music legend Willie Nelson ventured into the Air Force, embarking on a journey that would unexpectedly shape his path. However, after just nine months of service, Nelson faced a setback when he was medically discharged due to back issues.

The juxtaposition of Nelson’s serene demeanor with the rigors of military life may seem surreal. Yet, this brief stint in the Air Force marked a pivotal chapter in his remarkable life story, laying the groundwork for his future as an enduring musical icon.