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This dissertation examines the rights to free speech and parody by combining philosophical inquiries with legal analyses. Part One draws upon natural law theories to argue that the right to free speech is a universal right, and expressing oneself through parodies is an exercise of this right. It then discusses the nature of copyright from both natural rights and utilitarian perspectives, to illuminate how the right to parody copyrighted works is also a universal right that should be accommodated by copyright law. Regarding the scope of this right, because free speech is more fundamental than copyright, a broad legal definition of parody, which encompasses works targeting the originals as well as those that direct their criticism or commentary towards something else, is preferable to narrow definitions. However, parodies must not adversely impact the interests of rights holders by serving as market substitutes for the original works or their derivatives. Courts should also apply the parody defence or exception with reference to the free speech doctrine to ensure that lawful speech would not be suppressed for the sake or under the pretext of copyright protection.Part Two of the dissertation employs four case studies—the United States, Canada, the United Kingdom, and Hong Kong—to elucidate its arguments for a broad definition of parody and for courts to apply the parody defence or exception with reference to the free speech or freedom of expression doctrine. All four chapters explain how the free speech jurisprudences of these jurisdictions have been informed by the natural law, and how the proposed parody defence or exception would serve to bring their copyright jurisprudences, which have been influenced by utilitarianism, and/or a narrow conception of natural rights privileging the authors’ over the users’ rights, in line with their free speech jurisprudences. These studies also reveal the usefulness of the free speech/freedom of expression doctrine as an external mechanism in safeguarding parodists’ speech freedom. If this external solution would not be sufficient to protect free speech, then solutions within the copyright statutes would serve to create the needed breathing space for free speech.