Bob Ross is not a hard man to find.
Though he died in 1995, the late TV painter remains an omnipresent cultural staple. His Chia Pet perm, nap-inducing voice, and meme-worthy sayings — “Happy little trees!” — have transcended time. On YouTube, old episodes of his show, The Joy of Painting, boast ~450m views.
Online, you can acquire Bob Ross paints, Bob Ross brushes, Bob Ross underwear, Bob Ross coffee mugs, Bob Ross energy drinks, Bob Ross watches, and Bob Ross toasters.
But there’s one thing you won’t often see for sale: his artwork.
During his lifetime, Ross produced tens of thousands of paintings. Yet, only a handful of his works have popped up for sale in recent years. When they do appear, they often fetch $10k+ and attract dozens of bids.
Why is the work of one of history’s most prolific and accessible artists so scarce on the open market?
To find out, I spoke with art gallery owners, auctioneers, art collectors, ex-colleagues who worked with Ross, and the president of Bob Ross, Inc. — the company that preserves his legacy.
The man behind the canvas
Born in Daytona, Florida, in 1942, Ross dropped out of school in 9th grade to work with his father, 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.
Enjoying this article?
Get the Hustle’s 5-minute weekday roundup that keeps you hip to happenings in tech, business, and internet… things.
Inspired by the TV painter Bill Alexander, he started painting landscapes on gold mining pans and selling them at local markets in Alaska.
His income from painting soon surpassed what he made in the military. So, in 1981, he migrated back to Florida, trained under Alexander, and became a certified painting instructor.
Bob Ross strikes a happy pose (Photo: Acey Harper/The LIFE Images Collection via Getty Images)
Now, here’s where things took a wild turn for Ross:
- One of his students, Annette Kowalski, was “mesmerized” by the jolly painter and encouraged him to strike out on his own.
- They pooled together their life savings, launched Bob Ross, Inc., and set out to make Ross into a TV star.
- A PBS executive gave them a shot.
- The show — The Joy of Painting, which aired between 1983 and 1994 — was a huge hit and was broadcast on ~300 stations to 80m+ people every day.
In each 27-minute episode, Ross would paint one landscape from start to finish, shepherding viewers through his process with a soothing disposition, entertaining commentary, and an occasional guest appearance by his pet squirrel, Peapod.
Ross didn’t get paid for his shows. But Bob Ross, Inc. — which he partially owned — used the platform to sell paints, art supplies, workshops, instructional videos, and merchandise. By 1991, it was a $15m/year ($29m today) enterprise.
The actual paintings, though, were largely an afterthought.
Over the course of his career, Ross filmed 381 episodes of The Joy of Painting. For each episode, he painted 3 versions of the same artwork — one before, one during, and one after taping.
But his TV career only scratched the surface of his total output.
Pre-fame, in Alaska, he sold thousands of paintings. And even while famous, he painted nearly every day at seminars, events, and charity auctions in between tapings.
All told, Bob Ross churned out ~30k paintings in his lifetime — nearly 3x the output of Picasso, a prolific painter in his own right.
Zachary Crockett / The Hustle (painting © Bob Ross Inc.)
For years, collectors and fans have clamored to own their own piece of Bob Ross lore. Multiple art dealers told The Hustle that demand for his work is extraordinarily robust.
But Ross paintings are a bit like diamonds: vast in volume, scarce on the open market.
Major auction houses — Christie’s, Sotheby’s, Phillips — have no Bob Ross sales history. Craigslist draws a goose egg. A scan of eBay only turns up 3 sales in the last 6 months, 2 of which are of dubious origin.
Where the heck are those 30k paintings?
Bob Ross, Incorporated
As a part of Ross’s agreement with Bob Ross, Inc., the paintings he created for TV were work for hire, meaning the company maintained ownership of his work.
When Ross died in 1995, Bob Ross, Inc. (and thus, the paintings) became the sole property of Annette Kowalski and her husband, Walt.
Today, 1,165 Bob Ross originals — a trove worth millions of dollars — sit in cardboard boxes inside the company’s nondescript office building in Herndon, Virginia.
Joan Kowalski, Annette’s daughter, and the current president of Bob Ross, Inc., tells The Hustle that the company had never really given the paintings much thought.
“The paintings have always just sort of been here,” she says, with a chuckle. “We were sort of behind the times… it never occurred to us that anyone would want them.”
The company, which can be reached by dialing 1-800-BOB-ROSS, gets constant inquiries from folks about buying the paintings.
But they’re not for sale.
“Our only mission,” Kowalski says, “is to preserve the mythological wonderment that was Bob Ross.”
TOP: Joan Kowalski (top left; president of Bob Ross, Inc.) and Sarah Strohl (executive assistant) laugh at a social media post of a fan wearing Bob Ross socks; BOTTOM: Strohl sifts through some of the company’s many original Bob Ross paintings (Bill O’Leary/Getty Images)
Part of the reason Bob Ross, Inc. isn’t interested in selling the paintings is that it has far more lucrative assets on hand — like Bob Ross’s IP.
The company holds 154 copyrights, and numerous trademarks on Ross’s name and likeness, which they use to sell millions of dollars’ worth of Bob Ross-themed merchandise and instructional courses.
On occasion, Bob Ross, Inc. leases out a few paintings to galleries and exhibits around the country:
- 54 paintings can be seen at The Bob Ross Art Workshop & Gallery in New Smyrna, Florida.
- 27 paintings are at Minnetrista’s Bob Ross Experience in Muncie, Indiana.
- 4 paintings are in the possession of the Smithsonian National Museum of American History in Washington, DC.
But this only answers a part of the mystery. What about all the other paintings Ross gave away or sold during his life?
The open market
Jessica Jenkins, a VP at the Minnetrista exhibit, and a Bob Ross scholar, tells The Hustle that many more Ross paintings are actually hanging in living rooms across the US.
“He was always happy to donate his paintings to fundraisers, or sell his work at a reasonable price,” she says. “Many people who own one acquired it decades ago.”
For years, WIPB-TV — the PBS affiliate station in Muncie, Indiana, where Ross filmed most of his episodes — would auction off a Ross painting at its annual fundraising drive.
According to the town’s paper, The Star Press, these paintings were always “the most anticipated item,” overshadowing tickets to Cancun, diamond necklaces, rare Beanie Babies, and basketballs signed by Magic Johnson.
“We still have 4 of his paintings hanging here at the station,” says Lori Georgi, a director at WIPB. “People come from England just to see them.”
An old newspaper clipping advertises an auction for an original Bob Ross painting featuring “majestic snow-covered mountains, a tranquil lake surrounded by towering evergreens, and a beautiful sunset sky.” (The Star Press; Muncie, Indiana, 2000)
Before he became a TV star, Ross also sold thousands of his landscape paintings at flea markets, fairs, and malls, often for small sums of cash.
This is how Larry Walton, 82, of Crosslake, Minnesota, acquired his original Bob Ross.
Back in 1980, while working as a flight instructor in Alaska, he bought a scene with mountains and blue northern lights from the then-unknown “peculiar artist” at an Anchorage fair for $60.
It spent years sitting in the garage until his son — an avid fan of Bob Ross YouTube videos — thought the signature in the corner looked familiar.
When the couple decided to sell it, they turned to Modern Artifact, an art gallery and dealer in Minneapolis, Minnesota.
Ryan Nelson, the gallery’s owner, tells The Hustle that he’s been buying and flipping Bob Ross paintings for 10 years. To find sellers like Walton, he uses SEO tactics and places “wanted” ads in local newspapers near where Ross spent time.
“We buy and sell more of his paintings than any gallery on the planet,” he writes via email. “To retain that position, we offer more money to buy his paintings than most anyone is willing to risk.”
The Waltons sold the painting to the gallery for $10k; Nelson then flipped it on eBay for a small profit.
Unlike traditional art collectors, those who possess Bob Ross paintings tend to be ordinary folks who don’t know what they’re in possession of.
“Most families that have these paintings are not millionaires,” he says, “and the money is very impactful in their lives.”
An original Bob Ross painting up for sale on Modern Artifact’s website for $95k (Modern Artifact)
Modern Artifact has sold at least 34 Bob Ross paintings over the years.
Nelson wouldn’t divulge the sale prices, but said it’s not uncommon for them to go well beyond $10k. On the site, he currently has a rare ocean scene listed for $94k.
It may seem odd that Bob Ross paintings fetch that much at market.
After all, Ross often produced a painting in less than 30 minutes (by contrast, it took da Vinci 4 years to complete the Mona Lisa), and his artwork was, by design, highly replicable.
But Nelson chalks the crazy prices up to a combination of basic economic principles and social capital.
“The bottom line is supply and demand: Bob Ross paintings are extremely tough to find, and more people want them than can have them,” he says. “They’re also the ideal conversation pieces, since they are almost universally recognizable.”
A few Bob Ross classics. TOP: Wilderness Way, The Joy of Painting, S31, E13.; BOTTOM: Northern Lights,The Joy of Painting, S8, E13. (both © Bob Ross Inc.)
Lindsey Bourret, managing director of the art appraisal site Mearto, estimates that the fair market value of a Ross painting — the price it should sell for based on precedent — is $2k to $4k. But the pop culture element to his work boosts demand.
“I would personally categorize Ross’s work as a hybrid between fine art and entertainment memorabilia,” she says.
Some buyers are willing to pay a premium for that.
One collector who didn’t wish to be named out of concern for her privacy, owns an extensive cache of artwork, including several six-figure pieces. But she considers her Bob Ross original her “crown jewel.”“I’ve had more guests comment on my Bob than my Picasso,” she tells The Hustle. “It’s really all about the story.”
It’s all about the process
Ultimately, the real reason there aren’t more Bob Ross paintings up for sale is that the artist never wanted them to be a commodity.
For Ross, the value was in the process, not the finished product.
“He was about as uninterested in the actual paintings as you could possibly be,” says Kowalski. “For him, it was the journey — he wanted to teach people. The paintings were just a means to do that.”
NOTE: Top image of Bob Ross © Bob Ross Inc.; photo illustration by The Hustle
Get the 5-minute roundup you’ll actually read in your inbox
Business and tech news in 5 minutes or less