The paintings will be unveiled in early 2018 and will enter the gallery's permanent exhibition, which includes the only complete collection of presidential portraits in the United States outside of the White House.
Since former President George H.W. Bush, it is tradition for the President and First Lady to have their official portraits done.
But the selection of Wiley and Sherald by the Obamas carries another important legacy - one that goes beyond art itself.
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Former first lady Michelle Obama has announced her choice too, selecting Baltimore native Amy Sherald to paint her portrait. We definitely can not wait to see the paintings of the Obamas; they're sure to make us miss them even more. His rich, highly saturated color palette and his use of decorative patterns complement his realistic, yet expressive, likenesses. The artist has painted portraits of influential hip-hop figures like the Notorious B.I.G., LL Cool J, Big Daddy Kane, Ice T, Grandmaster Flash and the Furious Five and Michael Jackson, among others. Sherald won a National Portrait Gallery portrait prize previous year, and has a portrait in the Smithsonian National Museum of African-American History and Culture titled "Grand Dame Queenie".
Both artists are known mainly for their work painting African-American subjects with colorful backgrounds. The Smithsonian's announcement notes that "Sherald challenges stereotypes and probes notions of identity through her life-size paintings of African Americans".
The Portrait Gallery is now raising funds for the portraits, which will be unveiled in early 2018. He has occasionally discussed the positive impact Barack Obama's presidency had on artists creating images of non-white sitters.