George Lindemann Journal by George Lindemann - "Warhol and Basquiat at New York Auctions in May" @wsj by Kelly Crow

George Lindemann Journal by George Lindemann - "Warhol and Basquiat at New York Auctions in May" @wsj by Kelly Crow

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Andy Warhol's 'Six Self-Portraits' © The Andy Warhol Foundation for the Visual Arts/ARS, NY/Sotheby's

Want to bet on a painting? Be ready to hang onto it for a long time. That's a lesson to be gleaned from a group of artworks headed to auction next month in New York.

In late 1981, Maryland collector Anita Reiner stepped into the New York basement of dealer Annina Nosei's gallery and watched a 21-year-old street artist, Jean-Michel Basquiat, paint his self-portrait in the guise of a warrior king standing against a sunset-colored sky. Ms. Reiner bought it on the spot. On May 13, Ms. Reiner's heirs plan to resell the untitled work at Christie's for at least $20 million. Christie's specialist Brett Gorvy said the painting ranks among the artist's largest canvases, and it hasn't been seen publicly until now.

                                  
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Untitled work by Jean-Michel Basquiat The Estate of Jean-Michel Basquiat/ADAGP, Paris/ARS, NY/Christie's Images Ltd.

The Reiner Family Collection is also selling off six other pieces by artists like Robert Gober, Paul McCarthy and Urs Fischer, Mr. Gorvy added.

Over at Sotheby's, London stockbroker Barry Townsley is offering up Andy Warhol's "Six Self-Portraits," that the artist assembled for his last London gallery show in 1986. These so-called "fright wig" silkscreens show the artist wearing his signature wig and staring piercingly at the viewer. Four years ago, designer Tom Ford sold a wall-size, purple "fright wig" Warhol for $32.5 million at Sotheby's. On May 14, the house will ask at least $25 million for Mr. Townsley's group of 22-inch versions, which are silkscreened in differing candy colors.

Mr. Townsley declined to comment, but dealers say he has often told friends about the good-luck day he walked into Anthony D'Offay's gallery on the eve of Warhol's show and paid $57,500 for the six artworks. Sotheby's expert Oliver Barker confirmed the price but said he could not discuss the seller.

Write to Kelly Crow at kelly.crow@wsj.com