Katz painted his friend Kate as a study for a series of 11 larger paintings from 1993 to 1994 called Smile. The series shows women centred on black backgrounds smiling awkwardly, as if posing for photographs, their stiff composure suggesting vulnerability. Katz has been painting portraits of his family and friends in New York since the 1950s; these are now seen as precursors of Pop Art. Often grand in scale, they have a slick finish and detached manner with undercurrents of melancholia. Small oil paintings such as this one are sketched from life and often intended to be scaled up into larger works, but their economic execution and visible brushstrokes reveal an intimate side to his practice. He says, "A sketch is very direct. It is working empirically, inside of an idea."