The Elusive Hunt for Bob Ross Originals and What They Can Teach Us

GM GM.

When Dragon Ball Z moved channels and required a more expensive cable package that my parent would not get; I would watch Bob Ross on tv. That is why I went down this rabbit hole. Bob Ross is a cultural icon and one of the first people to introduce me to art and that maybe I too can have a pet squirrel as a friend lol (you can’t).

I recently saw a Bob Ross painting listed for $9.8 million USD, and not just any painting—this is the first painting from the Joy of Painting. Or as we in web3 like to say, his genesis mint haha. When I saw this, I immediately had the urge to understand what happened to all his work, and do most of them really go for this jaw dropping price? So grab some cold milk and buckle up.

Before we jump to how we got a $9.8m listing, lets go back in time how Bob Ross got to be who he is.

At 18, he joined the Air Force, moved to Alaska, and spent the next 20 years there as a drill sergeant, screaming at recruits. He was such a hard-ass that he earned the nickname "Bust 'em up Bobby."

It's kind of crazy; I would not expect Bob Ross to be a drill sergeant to begin with, or in the military. He didn't really get into the Bob Ross show to get paid; what he actually wanted to do is create a brand—that perm, the voice, the likeability — once he had a brand he would use his platform to sell paints, art supplies, workshops, courses, instructional videos, and merchandise.

By 1991, he was making about 15 million dollars a year, so about 29 million in today's prices. A lot of the paintings were really an afterthought.

Bob Ross definitely has a lot of paintings. He has over 30,000—estimated. He filmed 381 episodes of the Joy of Painting. He made about 1,600 during the TV show because he would do three painting: one before the show, one during the show, and one after the show. Then he also was painting beforehand and after for auctions and donating his time. So there's thousands of paintings out there, estimated to be about 30,000, which would put him substantially higher than the next person, which was Picasso.

His cultural impact and memeability (more on this later) has led to the mystique even after he passed away. He has a Netflix documentary, his YouTube channel's really big, he has an immersive Bob Ross experience where his former studio was. That's what's been driving a lot of his hype when thinking about his impact on culture as a whole, I remember vividly watching him in college when I would have a crazy night and having a hard time going to sleep, I would watch some Bob Ross to chill me out and go back to bed. Even 10+ years after my adolescence, Bob Ross continued to remain relevant.

Going back to the jaw dropping listing by the gallery (“Modern Artifact”). What I found interesting was the price; there aren't many paintings from Bob Ross that have gone over the six-figure mark, so this one is very high up. It's an attention-seeking kind of listing.

For context it is extremely hard to get a hold of an original Bob Ross painting. Although he has over 30k works, very few are in circulation. Another interesting thing is Christie's, Sotheby's, and Phillips have not had any Bob Ross sales history. Pricing art is a tough task but even the sales data is low it can be hard to really know what to offer or list at. A lot of Craigslist listings do not mention Bob Ross; there are a couple on eBay. Some look dubious in origin, some are legit, so it seems like there aren't many out there in circulation.

Part of that has to do with Bob Ross Inc., his holding company, which holds a lot of the paintings. They're essentially sitting in an office in Virginia. If they're holding most of it, that makes it pretty hard to get one, which drives up the demand and the price. The owner of Bob Ross Inc., the daughter of the original partner of Bob Ross, funded it from a financial perspective (Bob Ross's wife died; he's dead, so that is how they own this holding company). They're the last owners of this holding company, and they're not interested in selling his art.

"Bob Ross's paintings are like diamonds; they're vast in volume but scarce in the open market."-Ryan Nelson

It kind of goes back into the supply and demand loop. Although he has 30,000 paintings out there, estimated or that he's made, they're not all in circulation. So the demand is very high especially as his cultural relevant continues.

And it appears there aren’t many in this game or willing to put in the level of work required to attain these pieces, authenticate them and sell them. Ryan Nelson, the gallery owner from Minnesota, he says he uses local ads where Bob Ross spent his time or lived and drew. He uses SEO tactics to get the attention of people who may have a Bob Ross painting because some don't even know they have one. He was selling paintings before his show at fairs and other places, so they might not know they have it. He'll buy it off them, right off the bat, for 10k, then list it back well above the 10k he pays. He recently had a listing on his website for $94,000. Of course, the $9.8m USD one is the headliner for sure. When asked why he thinks there's a demand, he says there's more demand than pieces, so he sets the price at that point.

This content was brought to you by all the shitheads that decided to pay for this work. Consider subscribing or sharing with other people who may enjoy this.

Subscribe now

In reading about this listing and Bob Ross as a whole, I could not help see the similarities between the traditional art space and NFT space.

For example, this listing is the first of this collection that made Bob Ross who he is. The “genesis” mint/token some people value. I am not here to say whether it makes a difference or not to get the first in the collection but some collectors value this and this Bob Ross painting fits the bill. Regardless, it does bring headlines and people are talking about. It's a very Larry Gagosian kind of move.

Something interesting also that crossed my mind when doing a deep dive into all this was there are triptychs. It's kind of funny, the same behavior that we see in crypto is very apparent in the traditional art space as a whole or at least for this collection. For example, someone was selling the painting he did for an episode—the before, during the show, and after paints—for like $55,000 recently on eBay. It's kind of funny that someone would go out of the way to get all three. Just getting even one painting is hard, and someone taking the thought to get a triptych going is interesting. Crypto is very similar in that regard as well. Examples of this are in Pindar’s collections with bytegans people going after triptychs or Lucrece’s collection with his triptychs.

Going back to the cultural relevance or memeability from earlier. It's interesting reading about an art collector with tons of pieces, all worth multi-million dollars, including a Picasso. This collector, who refused to state her name, said her crown jewel, the piece that gets a lot of comments, is her Bob Ross painting, not her Picasso. It reminds me of crypto, where in your collection, you just buy what you like. If you like something, definitely buy it. It doesn't have to be from big names selling on Sotheby's and Christie's. Sometimes, the piece that gets the most attention is unexpected. For example, you could have a really nice xcopy piece, but the piece that gets the most attention is the meme. Having cultural relevance is important. It's hard to put a price on that, but cultural relevance does have a factor, and we might not see it at the time.

Right now, some of the meta in web3 is that the next bull cycle might see meme and meme coins (which we've already seen) run HARD. Meme NFTs, really solidify themselves in the space, whether they're fake rares or like the 6529 meme pieces or the Meebits meme pieces (NFA). Memes and cultural relevance is hard to attain but once you have it, it can be hard to fade that. Memes live forever and the classics are always worth revisiting. Going back to the collector with the Picasso piece. It's interesting, you know, what people value and what people don't, and art is always in the eye of the beholder, the person that's looking at it.

The National Museum of American History, Eric Jensch, was saying that he struggled choosing a painting that was a good representation for the Smithsonian or just for their cultural history relevance. The Smithsonian as a whole acquired fan letters and a bunch of other pieces to really tie in the impact that Bob Ross had on individuals and communities and how to help them better express themselves and feel better about themselves. I believe that is what makes Bob Ross resonate with so many.

He was really uninterested in actual paintings. For him, it was always about the journey, the story, and the feeling that he could convey to people. Basically, that they can do the paintings themselves, that they themselves can be an artist, and also unlocking that inner creativity for people. So I think that's pretty awesome. Like, he wasn't getting into this for the money or anything. Obviously, money is good for him to have financial stability, but for him, it was mostly teaching people, reaching people, and being happy with them.

Another bit of information was Bob Ross Inc., provides a service where they authenticate Bob Ross pieces. This is where blockchain tech can excel. Instead of having a central authority that deems a piece real or not, the blockchain can be our decentralized authority.

Lastly, in the 11 years that Bob Ross was painting during the TV show, there are very few instances where there was a human figure in the landscape. So he really was going for cultural relevance, fine art, emotions, and feelings versus drawing or depicting people. But the pieces that he did have with people in them, I think they should be appreciated as well. It will be interesting to see how those get valued, whether they're devalued or overvalued even more since they are rarer in his collection.

I’ve been doing more and more reading of artist/collectors and anyone that has had an impact on culture and art. Bob Ross is one of those people that was a fine artist ish but also an entertainer. Of course his work was cranked out at a pace and speed that most people would not value his work to a Picasso. But regardless, we can learn from the past and present.

The gap between traditional art and digital art is one I am seeing is smaller than I thought initially. I don’t know if we will see mainstream media crossover to web3 but it seems like a natural progression of where we are and where we go next. What do you think? Is it a fair price? As Larry Gagosion would say, everything has a price and the genesis piece of Bob Ross is worth exploring the price point on that.

Press the heart emoji or share with a friend, it helps with the algos. Want to give me feedback on this newsletter? Please select one of the below:

💸💸💸💸💸 - Super helpful thanks!

💸💸💸 - It was OK!

💸 - Not really!

Drop me a voicemail or note with any wins or fumbles you have had in Web3 recently.