By the mid-1970s, both Andy Warhol and Paul Anka were established celebrities in their respective fields. In 1972, Warhol created a series of four portraits of the singer, which he personally delivered to Anka in Las Vegas several years later.

Anka eventually used two of the portraits for the cover of The Painter (1976). Because the artworks had not been commissioned specifically for the album, Warhol received royalties from record sales in addition to his original payment for the portraits. According to Warhol's friend and Interview magazine editor Bob Colacello, the artist surprisingly disliked Las Vegas and was not particularly fond of Paul Anka's music, making their collaboration all the more unexpected. The remaining portraits later appeared on CD releases issued decades afterwards.