During election season, politicians and political campaigns often use pop culture or iconic works, such as viral memes or popular songs, to help convey their political messages — often without authorization from the copyright owners of these works. As politics and politicians become ever more divisive, these unauthorized political uses of copyrighted works can be particularly objectionable to copyright owners. In addition to offending their political or moral inclinations, artists and copyright owners frequently claim that these political uses infringe their copyrights. Politicians and campaigns argue that their right to use copyrighted works for political purposes is protected by the First Amendment, and that such political uses are presumptively fair use. This Article examines unauthorized political uses of copyrighted works under copyright law’s fair use doctrine to demonstrate that, in fact, both sides are correct. Through a series of case studies, this Article identifies a pattern in political fair use decisions: In disputes arising from the unauthorized political uses of copyrighted works, courts appear to implicitly modify their analyses and balancing of the fair use factors under Section 107 of the Copyright Act in order to both accommodate the import of political speech and to respect copyright owners’ dignity and rights to control use of their expressive works. Under the courts’ political fair use analysis, one determination — the nature of the original copyrighted work — seems to exert an outsized influence on the determination of all four fair use factors, permitting certain unauthorized political uses of copyrighted works to appear presumptively fair. This contradicts the Supreme Court’s guidance to courts on not subjecting copyright to independent First Amendment review nor to expand copyright’s fair use doctrine in infringement cases involving political or public figures. It also disregards certain copyright owners’ right to control use of their work, but permits other copyright owners the right to curtail infringing behavior that causes no market harm. This Article highlights these concerns and explores the normative implications of political fair use on litigation certainty and predictability, incentives to create political expressive works, and the balance between respecting creators’ dignity and rights to control use of their expressive works with guaranteeing free and open discussion of politicians and political candidates.