Conjure a mental image of George Washington and it will likely resemble his serious, unsmiling profile picture on the one-dollar bill. How we picture the first president is the legacy of 18th-century portrait painter Gilbert Stuart, whose experience painting the now iconic portrait was a challenge. George Washington’s dislike of having his portrait painted, and the dental pain he was experiencing, made him resistant to sit for Gilbert Stuart on the eve of his retirement from the presidency. This eventful portrait session is retold with a quick wit and fast pace for young readers. Funny details about how and why portraits were made at the time offer historical insights with modern meaning. For example, a page describing Gilbert Stuart as a celebrity painter includes an image with the text: “Here’s his selfie. (In the eighteenth century it’s known as a self-portrait.).” Acrylic, pencil, and digital illustrations evoke the time period and painting style in an unfussy, accessible, and entertaining manner. A timeline follows, as well as an explanation of George Washington’s tooth troubles, and more on the dollar bill engraving.