Jaime Garzón was a comic ahead of his time. While his comedy lifespan barely covered one decade (abruptly interrupted by his untimely death), his legacy in Colombian comedy and social activism remains strong. This article, rather than discussing his death, will focus on his life as a comedian who was the quintessential Colombian trickster. Through a framework of what it means to be a trickster in the Latin American and Colombian contexts, this article analyses the social commentary present in Heriberto de la Calle, Garzón’s most celebrated alter ego. Through de la Calle, Garzón was able to raise questions about our society and confront politicians about daily issues, both becoming a voice for average Colombians and establishing a new consciousness of comedy as a tool for social accountability. A discussion on the impact of Garzón’s legacy today will complete the analysis of his comedy and trickster discourse.