In 1991, Gilbert O'Sullivan sued Biz Markie for sampling without permission: this lawsuit, Grand Upright v. Warner, became a landmark case for music copyright, and for some scholars, represented a symbolic end to hip hop's golden age. This paper uses the lawsuit as a point of entry into debates about hip hop during a time of aesthetic transformation. Specifically, I present a corpus study spanning 1988–1993, consisting of hip hop songs of various subgenres drawn from Billboard charts. Unlike previous studies on this period, I consider both canonical artists, whose mastery of sampling is widely admired (such as Public Enemy), and more commercially successful artists (like the Fresh Prince), who used fewer samples. My study reveals a decrease in the average number of samples per song, and a radical shift in how these remaining samples are used. I situate Grand Upright at the intersection of legal institutions and musical aesthetics