Bob Ross

Served in: U.S. Air Force
Rank: Master Sergeant
Best Known For: Painting, The Joy of Painting
Est. Net Worth: $6 million

Before Bob Ross was teaching us all to paint, he was in the military. In 1961, when he was eighteen years old, Ross enlisted in the Air Force. He worked as a medical records technician. After he served, he starred on the show The Joy of Painting, which has remained a cult favorite even to this day.

Ross achieved the rank of Master Sergeant after spending twenty years in the military. He spent time in Alaska while in the USAF, and he later said that some of his landscape choices were inspired by the natural beauty of the Alaskan wilderness.