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The auction house said the painting, titled D Head XLVI, is part of a series the singer created between 1994 and 1997.
"The sitters ranged from band members, friends, and acquaintances and there were also some self-portraits," Cowley Abbott spokeswoman Andrea McLoughlin said. "It has been suggested that, for some of these important paintings, Bowie drew inspiration from the Ziggy Stardust era. With long hair and a pronounced profile, this energetic and enigmatic portrait is truly a rare representation from a celebrated artist."
The painting is being sold as part of Cowley Abbott's International Art Online Auction and is expected to fetch a high bid of $9,000-$12,000.