Of course, every depiction of a political figure as important and universally recognized as the president of the United States will be political. "I don't think there is anybody in my family who has ever had a portrait done, let alone a portrait that will be hanging in the National Gallery".
But well before he was selected to paint Obama, Wiley was recognized as a master of his craft worldwide, and his works have fetched as much as $143,000 at auctions.
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The first couple at a formal dinner with her arm placed lovingly on his back.
Obama joked that he had to tell Wiley to not make him "look like Napoleon" when the artist suggested he paint the former president riding a horse.
However, the former first lady went one step further, with a romantic gesture straight out of the classic playbook - she made Barack a Valentine's Day mixtape.
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In her remarks, Mrs. Obama expressed gratitude to those who came before her in her journey. Her body language, similarly to her husband's, is that of a person who is waiting for someone to give them a hard time.
When Barack's was first uncovered, he simply said "Look at that".
In the post, she called her husband her "best friend and biggest fan". "That's what I believe politics should be about", said President Obama. I am honored. I am proud. But it's important to remember that every presidential portrait functions to some extent as a work of propaganda.
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In the case of both paintings, many reacted with an understanding of the power that each portrait held politically, historically, and racially.