President Obama's A-List Pals
Credit: Jemal Countess/WireImage.com
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Oprah Winfrey
The OWN creator -- and longtime Chicago resident -- has been a loyal supporter of her fellow Chicagoans since the beginning. In fact, with Michelle, Sasha and Malia Obama out of the country in 2010 for his 49th birthday, the President celebrated his big day in Chi-town with Oprah and her pal Gayle King.