#10: Hugh Hefner

Rank: Private First Class, United States Army

Duration: 2 Years

In 1944, fresh out of high school, Hugh Hefner embarked on a unique journey by enlisting in the Army as an infantry clerk. Despite the demands of military life, Hefner’s keen eye for print media didn’t dim; he found an outlet for his creativity by contributing cartoons to Army newspapers.

This experience shaped his early years and planted the seeds for a more illustrious path that would later see him become an iconic figure in Hollywood and beyond. After being honorably discharged in 1946, Hefner’s time in the Army would become a formative chapter in his journey toward becoming the iconic founder of Playboy magazine and a cultural trailblazer.