‘The Fairest of the Not So Fair’ (2008) is a portrait of remarkable intensity. Striking in scale and standing over six and a half feet tall, this transfixing work is a testament to the superlative power of Amy Sherald’s preoccupation with single-figure portraiture that sits at the heart of her celebrated oeuvre. Dating from the pioneering years of the artist’s practice, the painting’s formal qualities directly foreshadow the artist’s mature visual vocabulary and distinct style.
‘The tradition of portraiture has become a way to reclaim time and space within an art historical narrative that is mostly starkly European... Artists of color are using portraiture to author a narrative of people that art history was written without. It speaks to the human condition and holds up a mirror to life.’—Amy Sherald
Reflecting upon Snow White, in title and content, the work depicts a woman in a yellow ballgown, holding a reflectionless mirror in her right hand. The woman’s gaze is obscured by a feathered mask, which was inspired by a watercolor illustration Sherald encountered in a book on traditional Brazilian dance costumes.  Accordingly, this painting illustrates Sherald’s early exploration of the gaze in portraiture as well as the relationship between subject and viewer, which is now a powerful characteristic of her practice.
Sherald renders the woman’s skin tone in her signature grisaille—here, a mixture of black and Naples Yellow—which sits in stark contrast to the bold and fluid colors that define the flat, highly saturated background. Typical of her practice, this choice diverts the viewer’s focus away from a subject’s individuality towards their whole humanity, which Sherald further describes through distinctive clothing and accessories. Through this technique, Sherald seeks to present an expansive vision of Black identity.
Sherald’s practice engages traditions of portraiture and American realism, genres that have historically unrepresented Black subjects whose lives are inextricable from the narrative of American art history. Sherald typically paints black Americans she encounters in everyday situations and asks to costume and photograph them. These photographs become the source material for her paintings, which she uses to directly address the history of representation, crafting narratives that restore a broader, fuller picture of American life.
‘The Fairest of The Not So Fair’ is thus a touchpoint of Sherald’s challenge to the dominant historical narrative of art, largely written by painters who were male and white, presaging her illustrious contribution to the evolution of portraiture. Speaking of her early work, Sherald reflects: ‘I stage specific scenes of social ascent, and racial descent that chart the psychology and performance of identity with a particular attention to notions of social exclusion and assimilation.’  Fittingly, the title seamlessly weaves fairly tale nostalgia with a self-assured demand to be seen.
Born in 1973 in Columbus, GA, and now based in Baltimore MD, Amy Sherald documents contemporary African-American experience in the United States through arresting, otherworldly portraits. Sherald subverts the medium of portraiture to tease out unexpected narratives, inviting viewers to engage in a more complex debate about accepted notions of race and representation, and to situate black heritage centrally in the story of American art.
Our new gallery space at 542 West 22nd Street is currently displaying solo exhibitions of work by Roni Horn and Paul McCarthy. The gallery is now open for timed viewing appointments. To book, please make a reservation and review viewing guidelines prior to your visit.
All Images: Amy Sherald, The Fairest of The Not So Fair, 2008 © Amy Sherald. Photo: Thomas Barratt; Amy Sherald in her studio alongside ‘The Fairest of The Not So Fair’, 2008 © Amy Sherald; Installation view ‘The Fairest of The Not So Fair’; Amy Sherald in her studio, 2019. Photo: Melanie Dunea; Hauser & Wirth New York, 542 West 22nd Street. Courtesy of Selldorf Architects. Photo: Nicholas Venezia
 Amy Sherald in Tyler Green’s ‘Amy Sherald, Lucio Fontana’, Modern Art Notes Podcast, podcast audio, 7 February 2019, https://manpodcast.com/portfolio/no-379-amy-sherald-lucio-fontana (accessed 23 February 2021).  Amy Sherald in ‘A conversation between Amy Sherald and Marc Payot,’ Ursula, 2019, online.  Amy Sherald, ‘Artist’s Statement,’ in ‘The Magical Real-ism of Amy Sherald,’ The Sonja Haynes Stone Center for Black Culture and History, Chapel Hill NC, 2011, p. 5.