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Born in 1977 in Los Angeles, California, artist Kehinde Wiley grew up in the city's South Central neighborhood, which exerted a profound influence on his practice. Encouraged by his mother, Wiley started taking art classes at the California State University conservatory when he was eleven years old. The following year he enrolled in a six-week art program through the Center for US/USSR Initiatives near Leningrad (today St. Petersburg). Wiley graduated from the LA County High School for the Arts and then went on to earn a BFA degree from the San Francisco Art Institute in 1999 and an MFA from Yale University's School of Art in 2001.

During a 2001 residency at the Studio Museum in Harlem, Wiley came across a starkly presented mug shot of a Black man from the New York Police Department. This led to Wiley's Conspicuous Fraud series of works and then his Passing/Posing compositions, which used Old Master paintings as models but transposed young Black men as heroic subjects wearing contemporary hip-hop clothing. The 2005 series Rumors of War extended this conceit to figures on horseback originally painted by Diego Velázquez and Peter Paul Rubens. Again, Wiley replaced the riders with Black men in athletic jerseys and Timberland boots. With Down in 2008, Wiley sought to reinterpret prostrate subjects like those in works by pre-1800 European artists such as Hans Holbein the Younger and Auguste Clésinger, here also inserting Black figures into the frame. For these different series, Wiley usually found his models by street casting, that is, looking for untrained naturals in New York City. Not only did Wiley use historic precedents for his work, but he also painted with a division of labor comparable to that of famous ateliers. Wiley would always render his figures personally, but he hired assistants to paint highly detailed backgrounds with rich patterning.

From 2008 to 2014, Wiley shifted his focus internationally, creating works in China, Nigeria, Senegal, Brazil, India, Sri Lanka, Israel, France, Jamaica, and Haiti. With the 2012 series An Economy of Grace, Wiley began painting female figures adorned in costumes designed by Riccardo Tisci, creative director of Givenchy. Perhaps the early peak of his still ascendant career, 2015 was a banner year for Wiley that included having a solo exhibition at the Brooklyn Museum of Art, winning the 2014 National Medal of Arts award, and being selected by former President Barack Obama to paint his official portrait for the Smithsonian's National Portrait Gallery. This already iconic painting shows Obama seated in a mahogany chair wearing a dark suit with a look of determination set amid a lush pattern of greenery and flowers, which is representative of Obama's ancestral, childhood, and adult homes of Kenya, Hawaii, and Chicago respectively.

After being widely celebrated for his Obama portrait, Wiley founded an artist residency, Black Rock Senegal, in the capital city of Dakar, where he sometimes lives and works. In 2019, Wiley created a large bronze sculpture, entitled Rumors of War, just like his prior series of paintings. This bronze was commissioned by the Virginia Museum of Fine Arts, Richmond and first displayed in Times Square in New York City. Based on the now controversial Confederate military equestrian type of statue common throughout the American South, and on Richmond's Monument Avenue in particular, Wiley's sculpture features a Black male with dreadlocks, a hooded sweatshirt, jeans, and Nike shoes. To this high-profile public installation, Wiley added another in 2021. For Manhattan's Penn Station, Wiley created Go, which consists of three ceiling-mounted, stained-glass panels. The colorful triptych in the new Moynihan Train Hall shows Black men and women breakdancing joyously with a backdrop of blue sky and gold-tinged clouds.