In Havana in 1964, Che Guevara is interviewed by Lisa Howard who asks him if reform throughout Latin America might not blunt the "message of the Cuban Revolution".
In 1955, at a gathering in Mexico City, Guevara first meets Fidel Castro. He listens to Castro's plans and signs on as a member of the July 26th Movement.
There is a return to 1964 for Guevara's address before the United Nations General Assembly in New York City, where he makes an impassioned speech against American imperialism, and defends the executions his regime has committed, declaring "this is a battle to the death."
March 1957. Guevara deals with debilitating bouts of asthma as his group of revolutionaries meet up with Castro's. Together, they attack an army barracks in the Sierra Maestra on 28 May 1957. After that, they begin to win over the rural peasant population of Cuba and receive increasing support, while battling both the government and traitors in their midst. Gradually, however, the government loses control of most of the rural areas. Soon afterward, the 26 July Movement forges alliances with other revolutionary movements in Cuba, and begin to assault towns and villages. Most fall to the rebels with little to no resistance.
On 15 October 1958, the guerrillas approach the town of Las Villas. The Battle of Santa Clara is depicted with Guevara demonstrating his tactical skill as the guerrillas engage in street-to-street fighting and derail a train carrying Cuban soldiers and armaments. Near the film's end, they are victorious. With the Cuban Revolution now over, Guevara heads to Havana, remarking "we won the war, the revolution starts now."
The second part begins on 3 November 1966 with Guevara arriving in Bolivia disguised as a middle-aged representative of the Organization of American States hailing from Uruguay, who subsequently drives into the mountains to meet his men. The film is organized by the number of days that he was in the country. On Day 26, there is solidarity among Guevara's men despite his status as a foreigner. By Day 67, Guevara, however, has been set up for betrayal. He tries to recruit some peasants only to be mistaken for a cocaine smuggler, and the Bolivian Communist Party, led by Mario Monje, refuse to support the armed struggle. On Day 100, there is a shortage of food and Guevara exercises discipline to resolve conflicts between his Cuban and Bolivian followers.
By Day 113, some of the guerrillas have deserted, and, upon capture, have led the Bolivian Army to the revolutionaries' base camp, which contained vast stockpiles of food, much-needed supplies, and intelligence identifying much of the group as Cubans. Much to Che's disappointment Tamara "Tania" Bunke, Guevara's revolutionary contact has botched elaborate preparations and given away their identity. On Day 141, the guerrillas capture Bolivian soldiers that refuse to join the revolution and are free to return to their villages. CIA and US Army Special Forces advisers arrive to supervise anti-insurgent activity and to train the Bolivian Army. On Day 169, Guevara's visiting friend, the French intellectual Régis Debray, is captured at Muyupampa by the Bolivian Army along with two of Che's last contacts with the outside world. A Bolivian airstrike then occurs against Che's guerrillas on Day 219, driving them deeper into hiding. By this time, Che has split his forces; his best fighters travel with him in one column, while another column contains other personnel, including Tania, and carries much of the remaining supplies.
Guevara grows sick and by Day 280 can barely breathe as a result of his acute asthma. Nevertheless, he continues to lead his group towards the other column of revolutionaries. On Day 302, the Bolivian Army wipes out the other column, killing Tania Bunke, Juan Acuña Ñunez, and several others in an ambush as they attempt to cross the Vado del Yeso after a local informant tells the Bolivian troops about the movements of the rebels. By Day 340, Guevara is trapped by the Bolivian Army in the Yuro Ravine near the village of La Higuera. Che is wounded and captured. The next day, a helicopter lands and Cuban American CIA agent Félix Rodríguez emerges to interrogate Che, but without success. The Bolivian high command then phones and orders Guevara's execution. He is shot on 9 October 1967, and his corpse lashed to a helicopter's landing skids and flown out.
In a final flashback scene, Guevara is aboard the Granma in 1956, looking out over the ocean, as the Cuban Revolution is about to begin. He sees the Castro brothers alone at the bow of the ship; Fidel is talking and Raúl is taking notes. Guevara hands a peeled orange to one of his comrades and returns his gaze to the lone brothers before the scene fades to black.
Benicio del Toro as Ernesto "Che" Guevara
Demián Bichir as Fidel Castro
Rodrigo Santoro as Raúl Castro
Santiago Cabrera as Camilo Cienfuegos
Catalina Sandino Moreno as Aleida March
Julia Ormond as Lisa Howard
Vladimir Cruz as Ramiro Valdés
Jorge Perugorría as Juan Vitalio "Vilo" Acuña
Benjamín Benítez as Rodolfo
Édgar Ramírez as Ciro Redondo
Armando Riesco as Dariel "Benigno" Ramírez
Néstor Rodulfo as Manuel "Miguel" Osorio
Jsu Garcia as Jorge Sotús
Elvira Mínguez as Celia Sanchez
Alfredo De Quesada as Israel Pardo
Roberto Luis Santana as Juan Almeida Bosque
Sam Robards as Tad Szulc
Victor Rasuk as Rogelio Acevedo
Kahlil Mendez as Leonardo "Urbano" Núñez
Marise Álvarez as Vilma Espín
Andrés Manuel Munar as José Iglesias Leyva
Unax Ugalde as Roberto "El Vaquerito" Rodríguez
Othello Rensoli as Harry "Pombo" Villegas
Norman Santiago as Carlos "Tuma" Coello
Pedro Telemaco as Eligio Mendoza
Jay Potter as Richard C. Hottelet
Stephen Mailer as Paul Niven
Jon De Vries as Eugene McCarthy
Joksan Ramos as Raúl Chibás
Javier Ortiz as Felipe Pazos
Michael Countryman as Adlai Stevenson II
Oscar Isaac as U.N. Interpreter and film narrator
Franka Potente as Tamara "Tania" Bunke
Gastón Pauls as Ciro Bustos (el Argentino)
Lou Diamond Phillips as Mario Monje
Joaquim de Almeida as René Barrientos
Yul Vazquez as Alejandro Ramírez
Marc-André Grondin as Régis Debray
Eduard Fernández as Ciro Algarañaz
Cristian Mercado as Guido Peredo Liegue
Jordi Mollà as Mario Vargas
Pablo Durán as Alberto "Pancho" Fernández
Óscar Jaenada as David "Dario" Ardiazola
Rubén Ochandiano as Eliseo "Rolando" Reyes
Ezequiel Díaz as Jorge Vázquez "Loro" Viaña
Carlos Acosta-Milian as Antonio Domínguez Flores
Antonio de la Torre as Carlos Fernández
Juan Carlos Vellido as Hernán Plata
Aaron Vega as José "Ricardo" Martínez
Roberto San Martín as Gary Prado Salmon
James D. Dever as Ralph "Pappy" Shelton
Mark Umbers as George A. Roth
Pedro Casablanc as Joaquín Zenteno
Tomás del Estal as Alfredo Ovando Candía
Giraldo Moisés as Israel "Braulio" Reyes
David Selvas as Andrés Selich
Enrique Arce as Carlos Pérez
Cristhian Esquivel as Mario Terán
Matt Damon as Father Schwarz
a two-part 2008 biographical film about Argentine Marxist revolutionary Ernesto "Che" Guevara
based on Jon Lee Anderson's 1997 biography Che Guevara: A Revolutionary Life.