Auction season is again upon us, and the collection of Emily Fisher Landau, a longtime member of the board of the Whitney Museum of American Art who also had a private museum, is taking center stage.

Sotheby’s won the honor of handling the estate, art from which comprises the most anticipated single-collector sales of the fall.

The auction is led by a painting by Pablo Picasso that is estimated at “in excess of $120 million.” The painting, Femme à la montre (1932), will be sold alongside works by Ed Ruscha, Jasper Johns, Cy Twombly, and Mark Rothko that are each expected to garner tens of millions of dollars.

Fisher Landau bought the Picasso in 1968, shortly after she began collecting (she famously brought her first purchase, a three-foot Alexander Calder sculpture, home on a city bus that same year).The Picasso was among her first major art purchases after receiving an insurance settlement from a jewel heist at her apartment. In the decades since, she amassed a distinguished collection of around 1,200 works displayed at her private museum, the Fisher Landau Center for Art, from 1991 to 2017.

The avid collector later donated a large number of her works to the Whitney—417 in 2010 alone—and served as a committee or board member at several other institutions including the Museum of Modern Art, Metropolitan Opera, SITE Sante Fe museum, and the Georgia O’Keeffe Museum.

Fisher Landau died in March at her home in Palm Beach, Fla., at the age of 102. The Sotheby’s sales include about 120 works from her collection.

Ed Ruscha 
Plenty Big Hotel Room (1985)

Ed Ruscha, Plenty Big Hotel Room (1985). Photo courtesy of Sotheby’s.

Estimate: $5 million–$7 million

There are multiple works by Ed Ruscha in the sale—no surprise considering his friendship with Landau, who held the largest collection of his work in private hands. But this one stands out. Ruscha is best known for his clamp paintings, such as the work Boss (1964), also included in the evening sale, that feature bold letters spelling out words on plain backgrounds. But with Plenty Big Hotel Room, he does something different and includes large black bars redacting the words he would have included that contrast with the American flag blowing in the wind. It is among the first paintings Ruscha made in which he begins to omit text rather than including it, which Sotheby’s called a “suggestive breakthrough.” It was also made in the first year Ruscha began including the American flag in his work.

Andy Warhol
The Shadow (1981)

Andy Warhol, The Shadow (1981). Photo courtesy of Sotheby’s.

Estimate: $2 million–$3 million

This is one of several Warhols offered between the day and evening auctions of the collection. Others include a pricier 1986 self-portrait with an estimate of “at least $15 million” in the evening sale, a portrait of Landau herself, and multiple lesser-valued works in the day sale. However, The Shadow—made with acrylic and silkscreen ink—is among Warhol’s most visually interesting works and returns to a motif from earlier in his career. It features the front profile of the artist outlined in black in front of a gray silhouette of his shadow. According to Sotheby’s, the work “reflects Warhol’s lifelong concerns with the transience of life.”

Glenn Ligon
Untitled (I Lost My Voice I Found My Voice) (1991)

Glenn Ligon, Untitled (I Lost My Voice I Found My Voice) (1991). Photo courtesy of Sotheby’s.

Estimate: $2.5 million–$3.5 million

This oil stick, gesso and graphite on wood panel work is not only visually striking, it carries “literal and metaphorical gravity” with the text layered on its surface, according to the Sotheby’s catalog. It’s one of the rarer works in a limited series Ligon made, known as his “Door Paintings.” Other examples from this series are held by museums including the Whitney and MoMA. “The present work stands as a fervent monument to the Black American fight for visibility, a poignant visual metaphor for the fragmented experience and representation of both the Black individual and artist in the United States,” the catalog reads.

Georgia O’Keeffe
Pink Tulip (Abstraction – #77 Tulip) (1925)

Georgia O’Keeffe, Pink Tulip (Abstraction – #77 Tulip) (1925). Photo courtesy of Sotheby’s.

Estimate: $3 million–$5 million

There are two works by O’Keeffe in the sale, including this oil painting acquired by Landau directly from O’Keeffe in 1985, a year before the artist’s death. O’Keeffe made the work a few years before a trip to Bermuda that may have set her on her course to New Mexico. The painting has been exhibited at the Brooklyn Museum, the National Gallery of Art in Washington, and the Georgia O’Keeffe Museum in Santa Fe. It’s also among more than 200 floral subjects O’Keeffe painted between 1918 and 1932 and an example of the careful experiments with abstraction that would carry on through her career. “O’Keeffe’s flowers remain her most highly sought after and influential paintings more than a century later, further underscoring her ingenuity and impact on the trajectory of 20th century art,” according to the catalog for the auction.

Nan Goldin
Couple In Bed, Chicago (1977)

Nan Goldin, Couple In Bed, Chicago (1977). Photo courtesy of Sotheby’s.

Estimate: $8,000–$12,000

This work was purchased by Landau from the Matthew Marks Gallery in New York in 1998. It is a rare Cibachrome print, and number 22 from an edition of 25. It is one of the few photographic works in the collection and was included in Goldin’s celebrated book, The Ballad of Sexual Dependency. Though not as well known as her Nan and Brian in Bed (1983), it is almost a precursor to it with similar subject matter and composition.

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