Prince first exhibited these check paintings in 2005 at the Gagosian Gallery in Los Angeles. The choice of location, near the heart of Hollywood, underscores the intersection of celebrity culture and personal narrative in his work. Prince's use of his own checks, sometimes featuring popular icons like SpongeBob, underscores his playful critique of both consumer culture and the art world's obsession with celebrity.

The jokes in these paintings, often stenciled over the checks, are characteristic of Prince's earlier works where he used humor to explore social and cultural norms. For example, a joke in one painting reads: "I accidentally shot my mother-in-law while deer hunting. It was an honest mistake. I came out of the tent in the morning and thought I saw a deer in an orange vest making coffee." This blend of crude humor and the personal nature of the checks creates a tension between the artwork’s aesthetic appeal and the provocative content of the jokes.

Prince's joke paintings are more than just visual gags; they are a commentary on the art world, celebrity culture, and the everyday transactions that underpin both. By using checks as a canvas, Prince blurs the line between high art and everyday life, challenging viewers to reconsider the value and meaning of both.

These works reflect Prince's broader artistic practice of appropriation and his skill in using humor to probe deeper cultural and social issues. His check paintings are a testament to his ability to turn the ordinary into the extraordinary, prompting viewers to question their own perceptions of art and value.