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Donald Roller Wilson’s paintings starring Cookie the orangutan regularly beat their estimates. This 2005 work, titled ‘Cookie!’, surpassed its $8,000-$12,000 estimate to achieve $28,000 plus the buyer’s premium in March 2023. Image courtesy of Palm Beach Modern Auctions and LiveAuctioneers.

Donald Roller Wilson monkeys with fine art traditions to great effect

NEW YORK – The fine art world tends to take itself seriously, perhaps too seriously. Donald Roller Wilson’s (b. 1938-) Old Master-style paintings of orangutans, chimpanzees, dogs, and cats, showing them in finery befitting royalty and engaged in human activities, invites viewers to reconsider and even poke fun at the seriousness of art.

“Donald Roller Wilson is known for his highly detailed, surrealist paintings of animals dressed in Victorian or other period clothes, engaging in all sorts of strange and hilarious activities. Some people might consider the subject matter kitschy, but that’s not a bad thing,” said Holly Sherratt, director of Modern and Contemporary art at Heritage Auctions, based in Dallas, Texas. “This blend of highbrow style and lowbrow subject makes the work appealing.”

Donald Roller Wilson’s 1980 painting of one of his favorite subjects, Cookie the orangutan, titled ‘It Had Been a Matter of No Sequence Which Found Cookie Being Held by Her Own Self, Serving as Her Own Mother,’ attained $55,000 plus the buyer’s premium in May 2018. Image courtesy of Heritage Auctions and LiveAuctioneers.
Donald Roller Wilson’s 1980 painting of one of his favorite subjects, Cookie the orangutan, titled ‘It Had Been a Matter of No Sequence Which Found Cookie Being Held by Her Own Self, Serving as Her Own Mother,’ attained $55,000 plus the buyer’s premium in May 2018. Image courtesy of Heritage Auctions and LiveAuctioneers.

Born in Houston, Texas, Wilson spent nearly 10 years as a university professor in Arkansas before dedicating himself to painting full time in the 1970s. His body of work showcases a cast of fictional characters that include Cookie the orangutan and Betty the chimpanzee.

Wilson’s paintings are chuckle-inducing at first glance, but also somewhat disquieting. In large works such as It Had Been a Matter of No Sequence Which Found Cookie Being Held by Her Own Self, Serving as Her Own Mother, which sold for $55,000 plus the buyer’s premium at Heritage Auctions in May 2018, he encourages the audience to ponder his artistic choices more deeply.

“The painting features the artist’s most beloved character, Cookie, depicted as both mother and child. Mother Cookie is portrayed as a queen, adorned in elaborate regalia,” Sherratt said. “The title of the piece invites psychological analysis, prompting questions such as why Cookie is depicted being held by herself.”

Exploring a dichotomy of good and bad behavior, this diptych by Donald Roller Wilson, ‘The Point of It’ and ‘The Butt of It’, brought $32,000 plus the buyer’s premium in November 2019. Image courtesy of Heritage Auctions and LiveAuctioneers.
Exploring a dichotomy of good and bad behavior, this diptych by Donald Roller Wilson, ‘The Point of It’ and ‘The Butt of It’, brought $32,000 plus the buyer’s premium in November 2019. Image courtesy of Heritage Auctions and LiveAuctioneers.

Wilson is an extremely skilled painter. He employs traditional painting techniques, but in the service of depicting subjects that are childlike and relatable. “Even if you think he’s silly, you must admit he’s incredibly talented. There’s also a dark side to his work. You might be drawn to the cute little chimp, but then discover that he’s half nude or engaged in some ‘naughty’ activity,” Sherratt explained.

“The characters attract us and then the narratives repel us,” she continued. “I hear clients exclaim, ‘That’s the cutest thing I’ve ever seen’, before they realize it’s something phallic. Viewers’ reactions can be as humorous as the art.”

Donald Roller Wilson’s untitled 1995 painting of Cookie the orangutan wearing a red dress made $32,000 plus the buyer’s premium in November 2019. Image courtesy of Heritage Auctions and LiveAuctioneers.
Donald Roller Wilson’s untitled 1995 painting of Cookie the orangutan wearing a red dress made $32,000 plus the buyer’s premium in November 2019. Image courtesy of Heritage Auctions and LiveAuctioneers.

While Wilson has painted a variety of animal subjects, including dogs and cats, his paintings of apes reign on the auction market. An untitled 1995 painting of Cookie wearing a red dress with a ruffled Victorian-style collar and an elaborate flower headdress made $32,000 plus the buyer’s premium in November 2019 at Heritage Auctions.

“The lace collar and floral crown evoke the Dutch Golden Age, reminiscent of styles you might see in a Rembrandt painting, who famously experimented with lighting and texture. It’s funny to draw such grand comparisons when, in fact, we’re looking at a primate adorned in this fashion,” Sherratt said.

She added, “We have a strong audience for Wilson’s work, and his prices have remained steady. Many paintings we’ve offered have exceeded the estimates, and some have even doubled the estimates.”

Donald Roller Wilson’s monkeys may bring the highest sums at auction, but collectors pounce on his cat-centric paintings such as ‘Judy ... Thinking’. This 1990 work secured $11,000 plus the buyer’s premium in September 2023. Image courtesy of Freeman’s Hindman and LiveAuctioneers.
Donald Roller Wilson’s monkeys may bring the highest sums at auction, but collectors pounce on his cat-centric paintings such as ‘Judy ... Thinking’. This 1990 work secured $11,000 plus the buyer’s premium in September 2023. Image courtesy of Freeman’s Hindman and LiveAuctioneers.

Wilson’s art is immediately recognizable, and he further distinguishes his works by giving them lengthy descriptive titles that are akin to short stories. The titles often appear in abbreviated form because they are too long for most auction catalog listing templates. This is true for Judy … Thinking,  the full title for which is actually Judy … Thinking (Knowing She Could Make Money Just by Seeing Something in Her Mind) … (Thinking She Could Get as Big a Tuna as She Wanted … or Maybe a Large Quantity of Cream … Just by Seeing It in Her Mind). The 1990 oil on panel of a cat in a yellow dress, her head ringed by wispy white dollar signs, brought $11,000 plus the buyer’s premium in September 2023 at Freeman’s Hindman.

Perhaps owing to the meticulous nature of Wilson’s paintings, fewer than 350 have crossed the block in LiveAuctioneers-hosted auctions. Buyers also seem keen to hang onto them, further stoking demand.

“Donald Roller Wilson’s production rate must be slower compared to artists who use quicker, looser styles, and the current owners likely form strong attachments to these works, making them reluctant to sell,” Sherratt said. “These paintings connect deeply with people, making the characters feel almost like friends. If you contact Wilson for details about his paintings, he won’t just provide titles and dates. Instead, he might discuss the characters as if they were family members or friends, even sharing quirky details like what Betty had for breakfast on a particular day.”

Detail of Donald Roller Wilson’s ‘Cookie!’, which is also shown in its elaborate frame. It beat its $8,000-$12,000 estimate to achieve $28,000 plus the buyer’s premium in March 2023. Image courtesy of Palm Beach Modern Auctions and LiveAuctioneers.
Detail of Donald Roller Wilson’s ‘Cookie!’, which is also shown in its elaborate frame. It beat its $8,000-$12,000 estimate to achieve $28,000 plus the buyer’s premium in March 2023. Image courtesy of Palm Beach Modern Auctions and LiveAuctioneers.

Wilson works featuring Cookie the orangutan are prized by collectors and typically sell far above their estimates. An endearing painting of a wide-eyed Cookie, wearing a green dress and a massive headpiece made up of flowers and even a bird, outperformed its $8,000-$12,000 estimate to sell for $28,000 plus the buyer’s premium in March 2023 at Palm Beach Modern Auctions.

In what may be a parody of, or homage to, the traditional still life format, Wilson painted an unusual triangular oil canvas in 6:33 PM NOV. 4th, SATURDAY  NIGHT. The 1978 painting, featuring a simian subject with an open-mouthed smile and wearing an elegant purple dress and a headpiece fashioned from fruit and vegetables, earned $29,000 plus the buyer’s premium in August 2021 at Lewis & Maese Antiques & Auction.

Donald Roller Wilson’s triangular 1978 oil on canvas ‘6:33 PM NOV. 4th, SATURDAY NIGHT’, featuring an ape in an elegant purple dress, went out at $29,000 plus the buyer’s premium in August 2021. Image courtesy of Lewis & Maese Antiques & Auction and LiveAuctioneers.
Donald Roller Wilson’s triangular 1978 oil on canvas ‘6:33 PM NOV. 4th, SATURDAY NIGHT’, featuring an ape in an elegant purple dress, went out at $29,000 plus the buyer’s premium in August 2021. Image courtesy of Lewis & Maese Antiques & Auction and LiveAuctioneers.

Wilson’s paintings frequently reference Old Masters and sometimes religion. A 1990 diptych, The Point of It and And the Butt of It, features Beverly the chimpanzee being both naughty and good, holding either a phallic- or missile-shaped object in her hands. Interestingly, she has a bright-while halo of light around her head in both scenes. The diptych brought $32,000 plus the buyer’s premium in November 2019 at Heritage Auctions. 

“Donald Roller Wilson crafts detailed paintings that blur the conventional boundaries between seriousness and playfulness,” Sherratt said. “His animal characters are so enchanting, you might start flipping through an auction catalog and end up impulsively adopting a naughty chimpanzee.”