Satirizing the art world was a regular thread through Brown's career. Feeling as though New York artists, dealers, and collectors looked down upon the Chicago scene, Brown was more than happy to fight back with sardonic wit and take-no-prisoners attitude. Lips of Gossip concerns itself chiefly with the art scene at large rather than an individual artist or dealer, chastising the gossip he would overhear at gallery openings. The format of the painting likely is a nod to Saint Sebastian, a popular Saint to soldiers and athletes who is said to have been executed by arrows, and was a perennial subject among Medieval artists.