South of the Border is a 2009 American documentary film directed by Oliver Stone. The documentary premiered at the 2009 Venice Film Festival. Writer for the project Tariq Ali calls the documentary "a political road movie".

The film has Stone and his crew travel from the Caribbean down the spine of the Andes in an attempt to explain the "phenomenon" of Venezuelan president Hugo Chávez, and account for the continent's "pink tide" leftward tilt. A key feature is also Venezuela's recent Bolivarian revolution and Latin America's political progress in the 21st century. Stone stated that he hopes the film will help people better understand a leader who is wrongly ridiculed "as a strongman, as a buffoon, as a clown."

In addition to Chávez, Stone sought to flesh out several other Latin American presidents whose policies and personalities generally get limited, or according to Stone, biased media attention in the United States and Europe, notably: Evo Morales of Bolivia; Cristina Kirchner and former president Néstor Kirchner of Argentina; Rafael Correa of Ecuador; Raúl Castro of Cuba; Fernando Lugo of Paraguay; and Lula da Silva of Brazil.