Bob Ross Paintings Bought on Craigslist Before the Boom Sell at Auction

Bob Ross paintings keep beating expectations at auction, especially when they come with an extra-special provenance.

Wooded Landscape with Stream, Bob Ross, wet-on-wet technique on canvas, signed, framed, inscribed to the canvas verso, 1987, 35 x 29 in., framed, sold for $65,000 at Caza Sikes.

When a Bob Ross painting comes to auction, it’s an event. So when Caza Sikes, a gallery and auction house in Cincinnati, Ohio, acquired two, Wooded Landscape with Stream and Mountain Landscape, they knew they had something special. The results of the Estates + Collections auction on September 15 proved them right when the paintings achieved hammer prices of $65,000 and $100,000, respectively.

“Ross was an important figure during so many people’s formative years,” principal auctioneer Graydon Sikes said in a statement, referring to the artist’s time as host of The Joy of Painting, which ran from 1982 to 1994. “He’s transcended the world of art and television and become a pop culture phenomenon. That, combined with the fact that his paintings just don’t come to auction very often, make these some of the best examples you can ever expect to find.”

Left: Wooded Landscape with Stream sold with two photos from 1987 of Ross with the painting at an event. The lot also included a certificate of authentication from Bob Ross, Inc. Right: The verso of Wooded Landscape with Stream is signed “To Jan / A very special friend / Happy Painting / Bob Ross.” An authentication seal from Bob Ross, Inc., is visible in the top right corner.

These two paintings have an unusual backstory. Will Sikes, a partner at Caza Sikes, told Cincinnati radio station WVXU that the consignor of the paintings “purchased them on Craigslist roughly 10 years ago.” He believes that, at the time of the purchase, the consignor had paid what “was probably a fair price,” but “far less than they are worth now.” Artnet reports that Ross has been in the top 10 auction results on their price database for the past 12 months. Caza Sikes gave each painting a pre-sale estimate of $50,000 to $75,000, which they considered conservative.

Mountain Landscape, painted in Bob Ross wet-on-wet technique on canvas, framed, inscribed to canvas verso, 1987, 35 x 29 in. frame, sold for $100,000 at Caza Sikes.

Going back a bit further shows that the paintings are different from the ones Ross did for his show and instruction books, and they demonstrate how much he meant to his fans. Both are inscribed “To Jan,” whom Ross went on to describe as a “special friend.” Jan is believed to have owned a now-defunct art store in Dayton, Ohio, that sold products from at least one of Ross’s sponsors. Photos accompanying the two paintings show Ross giving a demonstration at the shop, smiling for the camera and showing his progress on the paintings to an attentive crowd of fans.

Caza Sikes had both paintings authenticated by Bob Ross, Inc., and included each painting’s authentication certificate, as well as relevant photos from the demonstration, in the auction lots.

Left: Mountain Landscape was sold with two photographs of Ross, one with the painting in progress and one with a fan in a Bob Ross T-shirt, and a certificate of authentication from Bob Ross, Inc. Right: The verso of Mountain Landscape is signed and dated “To Jan, / Best wishes to a special friend / Happy Painting / Bob Ross / 1987.” An authentication seal from Bob Ross, Inc., is visible at the top right.

In the past year, paintings by Bob Ross have regularly reached six figures, with one passing the million-dollar mark, in auctions to raise funds for American Public Television. While the sales at Caza Sikes have a smaller scale, they carry extra meaning as souvenirs of an in-person meeting with Ross, a reminder that he was as beloved off-camera as he was on TV.

Images courtesy of Caza Sikes.

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Elizabeth Heineman is a contributing editor for Kovels Antique Trader. She previously wrote and edited for Kovels, which may have been the best education she could have had in antiques. Her favorite thing about antiques and collectibles is the sheer variety of topics they cover.