This week, the Netflix original film, Reptile, is serving as a sharp reminder of why Benicio del Toro is one of the best actors of his generation. And since we’ve already recommended three movies like Reptile, it’s time to shift gears and focus on the five Benicio del Toro movies that you should watch.

Considering that del Toro made his big screen debut in Big Top Pee-wee, followed by a bit part in License to Kill, he’s really come a long way in the last 35 years. Del Toro had a very small, yet memorable role in The Usual Suspects, and he was vastly underutilized in Marvel’s Guardians of the Galaxy. But neither of those films is among the films we picked for the five Benicio del Toro movies you should watch. Instead, we focused on the roles that pushed del Toro to a new level as an actor, including the movie that earned him an Oscar just over two decades ago.

Fear and Loathing in Las Vegas (1999)

Universal Pictures

Fear and Loathing in Las Vegas is such a bizarre movie that it could only be made by director Terry Gilliam. In this adaptation of Hunter S. Thompson’s novel, del Toro’s Dr. Gonzo and Johnny Depp’s Raoul Duke are on a drug-fueled trip to Las Vegas, ostensibly for work reasons. But they’ve seemingly never met a drug they didn’t like, and the duo doesn’t get much done when they’re tripping on acid while reality breaks down from their point of view.

This film is definitely not for everyone, and it divided critics when it was released. But there’s no denying that del Toro and Depp really threw everything they had into these oddball counterculture characters. That’s one of the biggest reasons why this film has become a cult classic.

Rent or Buy Fear and Loathing in Las Vegas on Google Play, Prime Video, YouTube, and Apple TV+.

Traffic (2000)

USA Films

Although del Toro was not the leading actor in Steven Soderberg’s Traffic, this turned out to be one of the most important movies in his career. Del Toro’s character, Mexican police officer Javier Rodriguez, was at the center of one of Traffic‘s three primary storylines, and the role earned del Toro an Oscar for Best Supporting Actor. Within the film, Rodriguez’s efforts to stop drug smugglers with his partner, Manolo Sanchez (Jacob Vargas), draw the attention of General Arturo Salazar (Tomas Milian).

Salazar offers Rodriguez the opportunity of a lifetime to dismantle one of the major cartels in Mexico. However, Rodriguez’s success comes at a high price when he realizes that his actions have only helped a rival cartel eliminate their competition. This places Rodriguez in a moral quagmire, and the big question of his storyline is how he can find his way out of it.

Watch Traffic on Prime Video.

21 Grams (2003)

Focus Features

Director Alejandro González Iñárritu’s 21 Grams is all out of order, but that was an intentional choice so that the stories of Jack Jordan (del Toro), Cristina Peck (Naomi Watts), and Paul Rivers (Sean Penn) could unfold in a nonlinear fashion. Del Toro and Watts were both Oscar-nominated for their roles in this film, which finds Christina holding a deadly grudge against Jack over the death of her husband, Michael (Danny Huston), and their two children.

Christina’s vendetta is partially justified because Jack is in fact responsible for the hit-and-run accident that claimed her family’s lives. Jack’s feelings of guilt are so overwhelming that he actually turns himself in. But that’s not enough for Christina, so she convinces Paul, the man who received her late husband’s heart, to help her murder Jack.

Watch 21 Grams on Prime Video.

Che (2008)

IFC Films

In certain circles, Ernesto “Che” Guevara (del Toro) is a beloved revolutionary figure. To others, he was a Marxist terrorist. Director Steven Soderbergh definitely seemed to take the former view when he helmed Che, which reunited him with del Toro in a massive two-part bio film about Guevara’s life. The first part of the movie largely deals with Guevara’s activities during the Cuban Revolution as he helps Fidel Castro (Demián Bichir), and his brother, Raúl Castro (Rodrigo Santoro), seize power after a bloody struggle.

The second part of the film chronicles Guevara’s ill-fated revolution in Bolivia, which is complicated by his failing health and other issues with his followers. Del Toro’s performance was widely acclaimed, and it’s easily one of his best movies. But because it was distributed by IFC, this film is only available to stream on affiliated outlets like AMC+.

Watch Che on AMC+.

Sicario (2015)

Lionsgate

Del Toro’s character in Sicario has an intriguing backstory as laid out in the film. Alejandro Gillick (del Toro) used to be a Mexican prosecutor until a personal tragedy led him to the CIA, which recruited him and trained him as an assassin. For most of the movie, Gillick is aligned with FBI Special Agents Kate Macer (Emily Blunt) and Reggie Wayne (Daniel Kaluuya). But it soon becomes clear to Kate that Gillick’s agenda doesn’t necessarily line up with her own plans.

This movie is more focused on Blunt than del Toro, but director Denis Villeneuve (Dune) and screenwriter Taylor Sheridan (Yellowstone) created one of the actor’s most memorable roles to date. That’s one of the reasons why del Toro was brought back in the sequel, Sicario: Day of the Soldado, as the primary character.

Watch Sicario on Fubo.

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