Ross was born in Daytona Beach, Florida, and was raised in Orlando, Florida. At the age of 18, Ross enlisted in the U.S. Air Force. Snow and mountains became a recurring theme in his artwork when the Air Force transferred him to Eielson AFB (in Alaska) and he first saw them. He developed his quick-painting technique in order to be able to create art for sale in short daily work breaks. He discovered that he was able to earn more from selling his work than from his Air Force position and later left the Air Force. After that, he began studying with Bill Alexander before Ross became famous worldwide with his television program, The Joy of Painting.