In her four years as First Lady of the United States, Barbara Bush had plenty of opportunities to contemplate the White House and its priceless artifacts. While some might gravitate toward the portraits of some of history’s most famous faces, Mrs. Bush found comfort in staring into the face of a person who many consider to be the ugliest woman to have stayed at the White House.

Lucy Ann Payne boasted a political pedigree that would be hard to surpass. Her sister, Dolley, married James Madison and became the fourth First Lady of the United States. When Lucy was fifteen years of age, she eloped with 22-year-old George Steptoe Washington, a nephew of the first President of the United States. Their marriage lasted for 16 years, ending upon George’s death in 1809. Three years later, Lucy was a bride again, this time marrying Thomas Todd, Associate Justice of the Supreme Court of the United States. Their wedding took place in the White House and was the first such ceremony within its walls.

Because of her storied history, Lucy’s portrait is part of the White House collection and hangs prominently in the Queen’s Bedroom on the second floor. All of the members of the Commonplace Fun Facts writing staff were raised by mothers who taught us that it is improper to comment negatively upon a lady’s appearance. Even so, even the most generous commentator would have to acknowledge that Lucy’s portrait is not exactly an idealized representation of traditional female beauty.

Despite its glaring imperfections, Barbara Bush said it was one of her favorite paintings. She knew that part her responsibilities as First Lady would be to sit for an official portrait. Unlike a photograph, a portrait allows the artist to take some artistic liberty to enhance the subject’s features, minimize imperfections and, in short, to make that person look better than reality.

Mrs. Bush had given a lot of thought to what future generations might think when they see Barbara Bush looking back at them from oil and canvass. With that in mind, she kept coming back to the image of Lucy Payne Washington Todd. She said,

“The reason I love her is . . . you look for an artist that flatters you. And here she is, with five o’clock shadow, balding, double-chins…. and you think, ‘And this flattered her? What do you think Lucy really looked like?'”

Mrs. Bush, incidentally, was famously down-to-earth and frequently made herself the object of her own humor. She readily admitted that her trademark necklace was made of fake pearls. She was also the first to point out that the reason she wore it was to hide the wrinkles on her neck.

If she truly had any reservations about how history would judge her based upon her portrait, those concerns should have been put to rest when it was unveiled. In addition to the trademark pearl necklace, the portrait’s eyes reflect her signature sense of warmth and humor.