Holly befriended John Wesley in the early 60's and supported his early career. In 1964 she commissioned him to paint her portrait. Early paintings of his dealt with flatness of figuration and the subjects were translated into cartoonish characters. In this portrait Holly is portrayed as a cartoon/pin-up of a female sailor. Her hand is waving in the air as if she is greeting a crowd or embarking on a journey and waving goodbye. Wesley's recognizable framing motif is used in a navy blue, further accentuating the sailor image. Two battleships serve as emblems flanking the top of the painting, forming a mantle of sorts above her strong but womanly image. The shapes within the work and the pin-up sailor image communicates Holly as transcending the male world in which she gracefully charmed, maneuvered and flourished. The painting, similar to Roy Lichtenstein's portrait of her titled, I'm Sorry... which she also commissioned in the same year, is a classic example of John Wesley's early iconic work.