Bob Ross Was a Drill Sergeant for 20 Years Before He Became a Beloved Artist and TV Star

Bob Ross is known to many pop culture fans around the world as the subject of a viral meme featuring “Happy Little Tree”. Ross (and his impressive perm hairstyle) is one of the most visible men on the Internet – however, even those who know about his time as a television star and popular painter, His past may not be known. Long before Ross starred in his own PBS TV series, he was serving his country as a member of the United States Air Force.

Bob Ross began his career as a respected military man

Bob Ross | AC Harper/The Life Images Collection via Getty Images/Getty Images

Ross was born in 1942 in Florida. Ross was a sensitive child and had developed attachments to several injured animals, which enabled him to return to health.

Ross dropped out of high school in the 9th grade and began training with his father as a carpenter. When he was 18 years old, Ross decided to enlist in the United States Air Force. According to, Ross was initially stationed in Alaska, which was a far cry from what he knew until now. He worked as a medical records technician before rising up the ranks to become a master sergeant.

Ross served in the military for 20 years, during which time he held a variety of positions and was often referred to as a tough guy. Speaking later about his experience as a drill sergeant, Ross said, “I was the guy who got you cleaning the toilet, the guy who made you your bed, the guy who got to work late. For shouts at you.” It was also during his time in the army that he developed his love for painting. Inspired by the beautiful landscapes he saw in Alaska, Ross took a few painting classes, finding solace and peace when he brushed the canvas.

When did Bob Ross become a TV star?

Ross began selling his signature weight-on-weight paintings when he was still a master sergeant in the Air Force. Eventually, he started making serious money as a painter, and he decided to retire from service and focus on his budding painting career.

Using sharp techniques he learned while painting over his lunch break, Ross became very successful. As a traveling tutor, Ross was content to do business with other people—until he was convinced by a former student named Annette Kowalski that he could be successful on his own. Ross, together with his wife and Kowalski, founded Bob Ross Inc.

In 1983, Ross launched his own PBS show, the joy of painting. Filmed in a small studio in Muncie, Indiana, the show ran until 1994, earning Ross fans worldwide who appreciated his simple, laid-back style. Reruns of the series continue to this day, and the joy of painting One of the contributing factors that led to the recent revival of Bob Ross.

When did Bob Ross die?

During his lifetime, Ross created literally thousands of paintings. He is considered one of the most prolific artists of all time. However, Ross aficionados are very unlikely to locate any of those pictures, even with a lot of searching.

According to, Bob Ross Inc. K actually has several paintings in storage, but prefers to have them on hand rather than listing them for sale. Paintings that have been on sale for years are paintings that first hit the market decades ago, and even those that sell for upwards of $10k.

As far as Bob Ross is concerned, he died in 1995 at the peak of his fame. At only 52 years old, Ross had a net worth of around $10 million. These days, fans love Ross for his legacy of positivity and calmness.

Where can you see Bob Ross’s lovely painting?

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