The landscape of drug policy in the United States has shifted dramatically in recent years, most recently evidenced by DEA's recommended rescheduling of cannabis. Cannabis legalization has been at the forefront of this movement, paving the way for a regulatory reset of other controlled substances as well, including psychedelics like psilocybin. This article aims to chronicle and analyze the parallels and divergences between these two legislative journeys, highlighting their historical contexts, regulatory frameworks, societal impacts, and the lessons learned for future drug policy reform efforts.