The season of dueling Basquiats is upon us, with two major paintings up for sale next month—one at Christie’s, the other at Sotheby’s. Together, they may bring in $100 million.

Christie’s will offer In This Case (1983), a large skull on a red background, in its New York evening sale of 21st century art on May 11. The canvas has an unpublished estimate of about $50 million. The following day, Versus Medici (1982) will be part of Sotheby’s contemporary art evening auction, where it is estimated to bring in between $35 million to $50 million.

“It’s going to be Basquiat versus Basquiat,” said Alberto Mugrabi, a private art dealer and collector. “They are both great paintings.”

The works come to market as demand for Basquiat is surging, according to dealers and auction executives. Just last month, Basquiat’s Warrior (1982) fetched $41.8 million at Christie’s Hong Kong, a new record for a Western artist in Asia. Last year, hedge-fund manager Ken Griffin paid more than $100 million for a major 1982 Basquiat owned by newsprint magnate Peter Brant during the pandemic lockdown.

The seller of the skull at Christie’s is Italian businessman Giancarlo Giammetti, a co-founder of the Valentino fashion house, according to a person familiar with the work. It used to hang in Giammetti’s Manhattan apartment, where it was photographed above his dining table in a 2013 Architectural Digest spread. Christie’s declined to comment on the identity of the seller. Giammetti could not be immediately reached for comment.

Installation view of Basquiat’s retrospective at the Fondation Louis Vuitton in Paris. Photo: Christie’s.

Skulls are among Basquiat’s most sought-after works. The symbol is part momento mori, an icon of death; part self-portrait; and part memorable logo, harkening back to Basquiat’s origins as a street artist.

Giammetti purchased the painting, which last sold publicly for $999,500 at Sotheby’s in 2002, from Gagosian in 2007. It is the last of three large skull canvases Basquiat made in successive years, according to Christie’s.

In This Case was included in the late artist’s blockbuster retrospective in 2018 at the Fondation Louis Vuitton, where the three skulls hung together. The other two are an untitled blue skull from 1982 that Japanese billionaire Yusaku Maezawa bought for $110.5 million in 2017, and a blue-and-peach one from 1981 in the collection of the Broad museum in Los Angeles. Maezawa’s work holds Basquiat’s auction record.

Christie’s rival Sotheby’s is hoping to strike gold with the seven-foot-tall Versus Medici, which Basquiat painted soon after an influential trip to Italy in 1981. The painting is among the artist’s “most forceful visual challenges to the Western art establishment, in which the young artist boldly crowns himself—the son of immigrants from Haiti and Puerto Rico—as successor to the artistic throne as established by the masters of the Italian Renaissance,” according to the house.

Art handlers with Basquiat’s Versus Medici (1982). Courtesy of Sotheby’s.

Only two other works by the artist have sold for more than $50 million at auction.

“Everything that relates to the new generation of Black artists, he was the beginning of all this,” said Alex Rotter, Christie’s chairman of 20th and 21st century art. “Without Basquiat, art history of the past 40 years would have been very different. He’s the most desirable artist at the moment.”

UPDATE, April 30: A previous version of this article stated that Giammetti purchased In This Case at Sotheby’s in 2002; in fact, he bought it from Gagosian in 2007.