Jeff Bezos, Lin-Manuel Miranda and Anna Wintour Among Honorees at American Portrait Gala

At the National Portrait Gallery’s third biennial American Portrait Gala on Sunday evening, stars from the worlds of entertainment, fashion, science, industry and technology converged to celebrate a diverse roster of portrait-worthy icons who are helping to lead our nation forward and define our culture — among them, Anna Wintour, whose award was being presented by fellow British ex-pat and late-night funnyman James Corden.: “He sent me a very seductive email.

The portrait of Wintour goes a long way toward letting us see the softer side of the famed editor: an informal photograph directed and chosen by Annie Leibovitz taken in Wintour’s home against the backdrop of her art collections, her family in the room but just outside of the frame. “She’s a great businesswoman and champion for the arts, but you never get the chance to see how unbelievably warm she is as a person,” said Leibovitz.

Miranda credited the Obamas for championing his efforts to tell this story, describing how in May 2009 when he was invited to perform at the White House, he was told, “We’d love for you to do a selection from…unless you have anything on the American experience? I had 16 bars about Alexander Hamilton. I had not finished writing this song.

Despite the nonpartisan stance of the Smithsonian, there was an inescapable political element in the crowd. “Where else could you be where you have two former First Ladies in the room on a school night?,” said the evening’s emcee Gayle King, giving a shout-out to attendee Hillary Clinton. “She is the first former First Lady [to have ever had a portrait] commissioned to be in the gallery. Once again, there you go Madam President — um, I mean, Madam Secretary — paving the way.

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