NEW YORK—A self-portrait collection assembled without spending a single dollar will be sold off at Bloomsbury Auctions on Sept. 24. The house estimates that the sale — which includes pieces by artists Jamie Wyeth, David Hockney, and Robert Motherwell as well as names like Maya Angelou, Muhammed Ali, and Gloria Steinem — could bring in a total of $500,000. The sketches belong to Burt Britton, a former bartender at downtown jazz club the Village Vanguard, who invited visiting literary and artistic personalities to draw a quick self-portrait...