Kehinde Wiley - 20th Century & Contemporary Art Day Sale, Afternoon Session New York Thursday, May 19, 2022 | Phillips

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  • Kehinde Wiley has carved a place in the canon of American portraiture for his paintings of contemporary Black sitters in compositions drawn from the traditions of Western portraiture. Inserting Black figures into a visual tradition that has been historically exclusionary, Wiley subverts these narratives while drawing attention to the relationship of painting to representation, power and status. With Big Daddy Kane, Wiley celebrates a key figure in the golden age of hip hop with a monumental portrait.

    "My job as an artist is simply to ask: who deserves to be on the great museum walls?"
    —Kehinde Wiley

    Wiley's portrait Big Daddy Kane is part of a 2005 series for VH1’s Hip-Hop Honors in which he was commissioned to paint each of the recognized artists, including LL Cool J, Ice T, and Grandmaster Flash and the Furious Five. The iconography of hip-hop is a prevailing interest in Wiley’s practice, though it is rarer that he has painted these famous hip-hop artists themselves. Big Daddy Kane (aka Antonio Hardy) is an American rapper who launched his career in 1986 with the Queens-based collective Juice Crew and further gained fame with hits including “Ain’t No Half-Steppin'" and “Smooth Operator.” As a lyricist, MC and entertainer, he revolutionized hip-hop fashion and introduced theatrics, choreography and costumes into performances, becoming hugely influential to a generation of MCs. Wiley’s VH1 commission later coalesced at the Smithsonian National Portrait Gallery in the exhibition RECOGNIZE! Hip-Hop and Contemporary Portraiture in 2008 and set the tone for some of his later work painting music giants, such as his 2009 portrait of Michael Jackson.


    In this eight-foot-tall, larger-than-life portrait, Wiley pays tribute to Big Daddy Kane by depicting the musician with lavish accoutrement typical of old masters portraits of nobles or aristocrats. Holding a commanding pose while exuding grace and nonchalance, Kane is surrounded with floral motifs, signature for the artist, rendered in opulent gold leaf. Big Daddy Kane merges hip-hop and classical iconographies by pairing Kane’s 2005 fashion with traditional white columns and by setting a microphone within a formal coat of arms. As Connie H. Choi describes, “by conflating the consumerism of hip-hop with the opulence of Old Master painting, Wiley brings the high-art world into the realm of popular culture at the same time that he deliberately moves away from the overt identity politics of the previous generation of African American artists.”i Big Daddy Kane celebrates the triumph of success within a nuanced and distinctly contemporary cultural interpretation.


    Big Daddy Kane, "Ain't No-Half Steppin'" (1998)



    i Connie H. Choi, “The Artist and Interpretation,” in Eugenie Tsai, ed. Kehinde Wiley: A New Republic (Brooklyn: Brooklyn Museum, 2015), pp. 23-24.

    • Provenance

      Roberts & Tilton, Los Angeles
      Acquired from the above by the present owner

    • Exhibited

      Washington, D.C., Smithsonian National Portrait Gallery, RECOGNIZE! Hip Hop and Contemporary Portraiture, February 8–October 26, 2008, p. 12 (illustrated)
      Boca Raton Museum of Art, January 7, 2013–January 7, 2018

    • Literature

      Sareet E. Yoseph, “Where Swagger Meets Stoicism,” The Root, May 16, 2008, online

    • Artist Biography

      Kehinde Wiley

      Applying the language and devices of royal portraiture to unnamed archetypes of the Black American experience, Kehinde Wiley bestows the pride and prestige of history painting to groups that it has too often overlooked. Rather than depicting the European aristocracy, Wiley’s portraits d’apparats place African Americans against florid backdrops and atop rearing horses, retaining the pomp and opulence of his historical antecedents and situating Black men and women dressed in everyday clothing as the subjects of art historical aggrandization. Often the accoutrements of urban life lend themselves quite readily to historical genres of portraiture; Air Jordans and Timberland boots can be as appropriate to monarchist might as emerald and ermine. Wiley’s goal is twofold: by subverting outmoded forms of expression through the substitution of the sitter, the artist criticizes the historical neglect of adequate Black representation and glorifies undeservingly maligned representatives of modern American life, what he calls “the ability to create painting and destroy painting at once.”

      Wiley’s work has been the subject of universal acclaim. His work can be found in the collections of major institutions across the world, including the Los Angeles County Museum of Art and the Wadsworth Atheneum, Hartford. Wiley was also selected in 2017 to paint the official portrait of President Barack Obama, the first Black artist to be given such an honor. Recently, Wiley founded Black Rock, an artist residency in Dakar, Senegal, bringing an important artistic resource to the African continent.

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Big Daddy Kane

oil on canvas, in artist's frame
106 x 82 1/8 in. (269.2 x 208.6 cm)
Painted in 2005.

Full Cataloguing

$150,000 - 200,000 

Sold for $189,000

Contact Specialist

Patrizia Koenig
Specialist, Head of Day Sale, Afternoon Session
+1 212 940 1279
[email protected]

20th Century & Contemporary Art Day Sale, Afternoon Session

New York Auction 19 May 2022