Unique silkscreen on huge, over-sized boxer shorts (sold with a Certificate of Provenance, indicating the work originates from the Estate of Andy Warhol, and thence, the Andy Warhol Foundation for the Visual Arts).

"Buying is much more American than thinking and I'm as American as they come. My favorite thing to buy is underwear." (A. Warhol, quoted in A. Warhol, The Philosophy of Andy Warhol: (From A to B and Back Again), San Diego, 1975, pg. 227).

In early 1962, Warhol was trying to transform from a commercial to a fine artist and was looking for an idea to distinguish himself from the other pop artists Roy Lichtenstein and James Rosenquist; who were also basing their works on everyday objects such as comic strips and billboards. Warhol's works at the time consisted of large flat paintings of Coca Cola bottles and comic book characters and his works were neither shown nor sold by any of the New York galleries. Desperate for a breakthrough idea that would distinguish him from his competition, he turned to his friend Muriel Latow who simply said to him: "you like money, you should paint pictures of money" (Andy Warhol: A Documentary, American Masters: Season 20, Episode 6, PBS, 2006).

The next day Warhol bought as many canvases as he could carry and painted the money pictures that helped launch his career. He returned to the subject in the 80's, and put the focus on the isolated symbol that denotes the US currency and titled them simply Dollar Sign.