The Office of the Solicitor General (OSG) has historically been very influential with the Supreme Court, especially as an amicus curiae in private litigant cases with an average win rate overall of 75%, and more than 90% in the Court’s patent cases. This Article is the first to consider OSG’s record in the Court’s copyright cases. It reviews all thirty-one of the copyright cases on which the Court granted cert since 1984. It contrasts the rarity of OSG’s participation in the Court’s twentieth century copyright cases with its predominant role in the Court’s twenty-first century cases. OSG’s analyses have been very persuasive in the Court’s copyright procedure and constitutional challenge cases, but less persuasive in the Court’s copyright remedies and substantive interpretation cases. The Article drills down into these divergences between OSG’s and the Court’s views in substantive copyright cases, finding some were highly divergent, while others had convergent outcomes but divergent analyses. In only one of the Court’s ten substantive interpretation copyright cases, Andy Warhol Foundation for the Arts, Inc. v. Goldsmith, was OSG’s merits argument highly persuasive with a majority of the Court. The Article reflects on why OSG and the Court so often differ in their interpretations of U.S. copyright law. It concludes with offering suggestions on how OSG might better improve its record as amicus in the Court’s future copyright cases.