Courts have struggled with the evaluation of parody under trademark law. While many trademark courts have protected parodies, there are a surprising number of cases that hold obvious parodies illegal. The problem is particularly severe with respect to parodies that are used to brand products, a growing category. The doctrinal tools that generally protect expressive parodies often don’t apply to brand parodies. Our goal in this paper is to think about what circumstances (if any) should lead courts to find parody illegal. We conclude that, despite courts’ increasing attention to speech interests in recent years, the law’s treatment of parody reflects too much uncertainty, leaving would-be parodists vulnerable to threats of legal action by trademark holders. In particular, given the flexibility of likelihood of confusion analysis, parodists’ fate is usually determined by the subjective judgment of courts, whose treatment of parody often seems to turn on instinct rather than trademark principles. We suggest some doctrinal tools that offer greater predictability and quicker resolution of parody cases, while avoiding some of the shortcomings of more traditional infringement analysis.