In October, Christie’s will auction works by Jean-Michel Basquiat, Joan Mitchell, Helen Frankenthaler and other Abstract-Expressionist and Neo-Expressionist artists from a private collection under the title “A New York State of Mind: An Important Private Collection.” Alongside a $25 million Cézanne watercolor, the works will go up for sale on October 6 at Christie’s New York headquarters.

Among the highest-priced lots in the newly merged category auction is a 1984 portrait by Jean-Michel Basquiat titled MP. Estimated to sell for between $4 million–$6 million, the painting depicts Basquiat’s friend Michael Patterson standing against a stark neutral background flanked by Xeroxed text listing blues songs. The seller bought the work at Christie’s nearly three decades ago, in 1993, for just $77,300. Prior to that it was shown only once, in 1985 at Akira Ikeda Gallery in Tokyo, before going to a Japanese collector.

Figurative portraits of real-life sitters are rare in Basquiat’s oeuvre and only one other has ever been sold on the secondary market. The other 1984 comparable, also titled MP, which features a similar composition, last sold in 2011 during a Sotheby’s contemporary sale in Paris for $1.7 million. The Basquiat works that command the highest prices are from 1982 to 1984 and include the artist’s most recognizable emblems, such as skulls, crowns, and graffiti-like scrawled text. As the Basquiat market matures, auction houses are introducing works with less familiar imagery on the secondary market to potential buyers.

Another highlight from “A New York State of Mind” is Joan Mitchell’s Untitled painting from 1958–59. The work is representative of the artist’s painterly style developed in the mid-’50s as she became a formative member of the New York School. It is estimated at $3.5 million–$5.5 million.