The Untold Tragedy of Bob Ross
Bad Money Bad Money
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 Published On Jun 10, 2023

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Toward the end of his TV career, Bob Ross stood atop a $15 million empire of live classes, art supplies, and how-to books.

But if you buy one of the many Bob Ross products out there today, do you know who the money really goes to? You may not like the answer to that.

While to many people Bob Ross symbolizes a life committed to artistic creation and the joy of painting, his life signified something way darker and more frightening: the exploitation of one’s image in the name of profit and greed.

This is the tragic story of Bob Ross that includes deathbed marriages, last-minute estate changes, business and family betrayals, CIA-style tape recordings, and even a former CIA agent.
Robert Norman Ross was born in Daytona, Florida, in 1942. He dropped out of school in 9th grade to work with his father as a carpenter.

At 18, he joined the Air Force and moved to Alaska, where he’d spend the next 20 years as a drill sergeant screaming at recruits. He was such a hard-ass that he earned the nickname “Bust ’em up Bobby.”

But his life changed when he discovered art.

Watching TV one day, he caught Bill Alexander, a German painter who had a PBS show called “The Magic of Oil Painting,”. Bob was instantly hooked.

He became one of Alexander’s traveling instructors and later gained his painting instructor certification. Alexander was using what’s called “wet on wet” technique, which Bob later adopted.

Despite his obvious talent as an artist, Bob’s early years as a painter weren’t all that profitable. Being Alexander’s star student didn’t pay very well, and the few paid lessons that he managed to arrange barely covered the bills.

In an attempt to save money on haircuts, he let his hair grow, he got a perm and decided he would never need a haircut again. Bob actually disliked the hairstyle, but his perm had later become an integral part of his public image and he felt that he was stuck with it. So he decided to keep his curls.

Trying to cope with the loss of her son, Annette Kowalski took one of Bob’s classes, and she was mesmerized.


Annette was the wife of Walt Kowalski, a former CIA agent with cold shark eyes. The pair saw Bob’s potential and were set to make him a TV star. Together with Bob and his wife Jane, they launched Bob Ross, Inc. Or BRI.

In 1983 “The Joy of Painting” premiered and PBS stations across the country quickly picked it up, rocketing Bob to television stardom, airing until 1994 and broadcasting on 277 stations to over 80 million people daily, the brand of Bob Ross was born making him a competitor to his former mentor.

00:00 - Intro
00:52 - Tidio
02:07 - The happy artist
04:47 - We're in business
08:42 - Unhappy accidents
10:07 - The show must go on
14:00 - Life after Bob
17:57 - Bob's legacy

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