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Long story short: Original Bob Ross paintings are so expensive, you could use the money and buy yourself something like this instead..
If you have seen more than five episodes of 'The Joy of Painting' you probably thought about buying an original Bob Ross painting. How hard can it be to get one? There are over 400 episodes of 'The Joy of Painting' and Bob did three copies of every painting on the show. So there should be over 1200 paintings from the TV show alone out there, and some of them just have to be on eBay or some other website.
So you open up your favorite search engine, try your luck with something like "Buy Bob Ross Painting" and are greeted with pages upon pages of Bob Ross replica paintings: