In the 1980’s and 1990’s, hip hop went through a formative transformation, where instrumentation moved away from drum machine and live bands and towards the art of sampling, where sections of existing songs were looped and overlapped to make a new song. While popular, this resulted in extended legal battles, as sampled artists were not credited, consulted, or compensated for the new works. Today, generative AI art models like Stable Diffusion and language models like ChatGPT are becoming incredibly popular. These models are trained on billions of images and documents collected from the web, generally without the creators' knowledge or consent. Mirroring the explosion of sampling, this has also resulted in legal action - highlighting a resetting of the AI playing field. This session will feature a diverse panel of experts in law, AI, technology, and music. It will explore the parallels between the two trends, how music’s trajectory might give us insight into AI’s future, and the important role fairness, humanity, and creativity have in leveraging new technologies.