Amy Sherald - 20th Century & Contemporary Art Evening Sale New York Tuesday, November 15, 2022 | Phillips

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  • In Amy Sherald’s Pilgrimage of the Chameleon, 2016, a young Black man stands tall, smiling gently at the viewer. Rendered in the artist’s signature grisaille palette, her figure wears a navy peacoat with a fur collar, a neat white button-down shirt, and khaki trousers, and he holds a rainbow bunch of balloons in his right hand. The balloons against a sky blue background serve as a natural symbol of uplift, implying the upward direction of the protagonist’s pilgrimage. 

    Pilgrimage of the Chameleon challenges stereotypical ideas surrounding young Black men. The professional costume of Sherald’s protagonist reminds one of respectability, the phenomenon of the late 19th and early 20th centuries wherein Black Americans felt pressure to conform to, as journalist Aysa Gray calls it, “the systemic, institutionalized centering of whiteness,” which still impacts Black Americans today.i


    The Stevens family outside of their home in Linn Creek, Missouri, c. 1905.

    This process of assimilation via respectability involves more than just physical appearance; as social justice writer Odochi Ibe notes, a Black person may feel obligated to change the way they speak or behave to blend in, or even to protect themselves from racist violence, and this can have a negative effect on one’s mental health.ii This process, called code-switching, is an exhausting performance of multiple identities based on one’s social, racial, and class context.iii Amy Sherald remembers her mother telling her to “speak a certain way and act a certain way” on her first day at a predominantly white private school.iv By young adulthood, Sherald had difficulty knowing who she was, “because I’d been performing my whole life.”v This lifetime of performing drew her towards painting portraits of other Black performers. While earlier works, such as Madame Noire, 2011, present more theatrical subjects, others, such as Pilgrimage of the Chameleon, show everyday performers: performers of whiteness, of respectability.

    Like Sherald, the young man in Pilgrimage of the Chameleon is a performer. He is ready to adapt his persona, like a chameleon, to whatever social situation he finds himself in. His button down and khakis are reminiscent of a private school uniform, or everyday office attire. His hairstyle is short and unremarkable, his face fresh. By means of his style and dress, the young man in Pilgrimage of the Chameleon fashions a calm, non-confrontational, upwardly-mobile persona. His rainbow balloons express a sense of optimism, a hope that these measures will reap social rewards.


    Bo Bartlett, Object Permanence, 1986. Sherald cites this work directly as the one that inspired her most as a Image: Columbus State University, Bo Bartlett Center, Artwork: © 2022 Bo Bartlett / Artists Rights Society (ARS), New York

    As a child, Sherald took a pilgrimage of her own, on a school field trip to an exhibition of Bo Bartlett’s work at The Columbus Museum in her hometown of Columbus, Georgia. This childhood experience had a significant impact on the artist, which she recalls often in interviews. Seeing Bartlett’s work was the first time Sherald saw a Black person in a painting of monumental scale, and this early moment of representation had a lasting effect on her desire to paint people who looked like her.

    Inspired obliquely by Bartlett’s realism, in combination with the lack of Black representation by other painters, Sherald learned to draw the human figure by copying photographs. Drawing from photography remains a fundamental aspect of her portraiture process. Once Sherald has chosen the model for a portrait, she takes hundreds of photos of them over the course of several hours. These photos are Sherald’s version of sketching, and she builds her painted portrait from this source material.vii
    "[I love] the stillness of daguerreotypes, the beauty of black skin in black and white pictures, how everything came down to what the eyes were saying. And in those photographs they are all telling stories, from the youngest child to the oldest person. When I look at images from that period, in my mind, I stand simultaneously with them in their deliberate gaze, and I understand and know that I am their future self, and dream."
    —Amy Sherald 
    Pilgrimage of the Chameleon shows the influence of early photography on Sherald’s artistic practice. With his greyscaled skin and timeless, simple costume, it is easy to imagine the young man in a black and white photograph, back in time.


    Tintype photograph of an unknown young man, 1870s.

    Sherald cites Frederick Douglass’s passion for photographs of Black people as a source of thematic inspiration for works such as Pilgrimage of the Chameleon. Douglass, as a public figure in the late 1800s, had his photograph taken often; sitting for over 160 portraits, he was the most photographed man in the 19th century.viii


    Sherald explains Douglass’ motivations, saying that he sat for so many portraits “to ensure the accurate portrayal of Black Americans.” She continues: “he discovered that the photograph had the ability to redefine the often stereotypical image and narrative of Black Americans.”ix Sherald, like Douglass, believes in the power of representation to challenge racist assumptions about Black people. Her painted portraits and Douglass’ photographs both present self-assured Black subjects, whose identities are products of their own creation. With Pilgrimage of the Chameleon, Sherald builds the legacy of representation that she wants to see in the world.



    i Aysa Gray, “The Bias of ‘Professionalism’ Standards,” Stanford Social Innovation Review, June 4, 2019, online.
    ii Ibe, “Playing the Game of Respectability Politics, But at What Cost?”
    iii Priscilla Frank, “’Fairytale’ Paintings Show a Side Of Black Lives History Overlooks,” The Huffington Post, July 7, 2016, online.
    iv Ibid.
    v Amy Sherald, in conversation with Russell Tovey and Robert Diament, Talk Art [podcast], September 27, 2022, 15:24.
    vi Amy Sherald, “Amy Sherald Speaks at The Columbus Museum” [video recording of lecture], September 29, 2017, online.
    vii Amy Sherald, Talk Art.
    viii “Frederick Douglass: Agitator,” American Writers Museum, accessed October 13, 2022, online
    ix Amy Sherald, quoted in Elaine Sexton, “Making Mirrors: A Micro-Interview with Amy Sherald,” Tulepo Quarterly, October 14, 2016, online.

    • Provenance

      Monique Meloche Gallery, Chicago
      Acquired from the above by the present owner in 2016

    • Exhibited

      Chicago, Monique Meloche Gallery, Amy Sherald: A Wonderful Dream, June 11–August 27, 2016, n.p. (illustrated; detail illustrated; installation view illustrated)

    • Literature

      Priscilla Frank, "'Fairytale' Paintings Show A Side of Black Lives History Overlooks," Huffpost, July 7, 2016, online (illustrated)
      Elaine Sexton, "Making Mirrors: A Micro-Interview with Amy Sherald," Tupelo Quarterly, October 14, 2016, online (illustrated)
      David Morgan, "Portraitist Amy Sherald," CBS News, February 18, 2018, online (illustrated)
      Public Art, no. 181, October 2021 (illustrated, n.p. and on the cover)

    • Artist Biography

      Amy Sherald

      Amy Sherald reflects on the contemporary African American experiences through her arresting and unearthly paintings. Her grisaille portraits call to the surface unexpected narratives and unfamiliar experiences of the every day, encouraging viewers to reconsider contemporary portrayals and accepted notions of race, representation, and the Black American experience.

      Sherald’s paintings are at once vivid and unassuming, offering silent, unflinching meditations on contemporary lived experience. She renders her sitters in a grisaille tone to disarm preconceived notions and misconceptions of Black identity. Vibrant, mute, and surreal in the ordinariness they portray, her work offers the viewer silence for placid and direct reflection. Sherald’s work has been widely acclaimed as the artist was the first woman and the first African American to win the prestigious Outwin Boochever Portrait Competition from the National Gallery of Art in Washington, D.C., and in 2019, the museum unveiled her official portrait of First Lady Michele Obama. Sherald’s work has been shown in solo exhibitions at the Contemporary Art Museum Saint Louis; the Crystal Bridges Museum of American Art in Bentonville, AR; and the Spelman College Museum of Fine Art in Atlanta, GA.

      View More Works

Property of a Private North American Collector


Pilgrimage of the Chameleon

signed and dated "Amy Sherald ♥ 2016" on the reverse
oil on canvas
72 x 51 1/8 in. (183 x 129.8 cm)
Painted in 2016.

Full Cataloguing

$1,800,000 - 2,500,000 

Sold for $2,087,000

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Amanda Lo Iacono
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20th Century & Contemporary Art Evening Sale

New York Auction 15 November 2022