Benicio Del Toro’s Career: From ‘Big Top Pee-wee’ to ‘The Phoenician Scheme’

Benicio Del Toro has built a career playing complex and memorable characters. His journey in film began with small roles, but his unique presence and intense acting style quickly set him apart. He is known for his ability to transform for his roles and bring depth to every character he portrays, from quirky sidekicks to leading men. Over the decades, he has worked with acclaimed directors and amassed a body of work that showcases his incredible range as an actor.

From his early days in Hollywood to becoming an Oscar-winning actor, Del Toro’s path has been defined by bold choices and powerful performances. He often plays characters who exist in the gray areas of morality, making them fascinating to watch. His commitment to his craft is evident in every film, establishing him as one of the most respected actors of his generation and leading him to his latest project, ‘The Phoenician Scheme’.

‘Big Top Pee-wee’ (1988)

Benicio Del Toro made his film debut in this comedy as Duke, The Dog-Faced Boy. The movie follows Pee-wee Herman as he joins a circus, where he meets a variety of eccentric performers. Del Toro’s role was minor, but it marked his first appearance in a major motion picture, launching a long and varied career.

The film itself received mixed reviews, but it served as a starting point for the young actor. Appearing in a mainstream comedy was an unusual start for an actor who would become known for his dramatic and intense roles. It was a brief but notable first step into the world of cinema.

‘Licence to Kill’ (1989)

In the sixteenth James Bond film, Del Toro played Dario, a menacing henchman for the main villain, drug lord Franz Sanchez. At just 21 years old, he became one of the youngest actors to play a primary villain’s enforcer in the Bond series. His character was a significant threat to James Bond, known for his sinister presence.

Del Toro’s performance as the ruthless Dario was memorable and showcased his ability to play intimidating characters. The role was an early indicator of his talent for portraying dark and complex figures. His part in a major franchise like James Bond brought him wider recognition in Hollywood.

‘The Usual Suspects’ (1995)

Del Toro had his breakthrough role as the peculiar and unintelligible criminal Fred Fenster. The film is a crime thriller about a group of criminals who are brought together for a police lineup and end up planning a major heist. Fenster’s mumbling speech and distinctive style made him a standout character in the ensemble cast.

Del Toro created Fenster’s unusual speech pattern because he felt the character’s main purpose was to die and wanted to make the part more memorable. The choice paid off, earning him an Independent Spirit Award and establishing him as a talented character actor. The film became a cult classic, celebrated for its complex plot and strong performances.

‘Fear and Loathing in Las Vegas’ (1998)

Del Toro underwent a significant physical transformation to play Dr. Gonzo, the attorney and companion to Johnny Depp’s character, Raoul Duke. To accurately portray the character from Hunter S. Thompson’s novel, Del Toro gained over 40 pounds. The film follows the duo on a drug-fueled journey through Las Vegas.

Directed by Terry Gilliam, the movie was initially met with mixed reviews but has since become a cult favorite. Del Toro’s commitment to the role and his chaotic performance alongside Depp were central to the film’s surreal and wild energy. His portrayal captured the spirit of Thompson’s gonzo journalism.

‘Traffic’ (2000)

Del Toro delivered an Academy Award-winning performance as Javier Rodriguez, a Mexican state police officer caught in the complexities of the war on drugs. The film interweaves multiple storylines, showing the drug trade from the perspectives of law enforcement, politicians, and users. Most of his lines were in Spanish, a challenge he embraced for the role.

His portrayal earned him the Oscar for Best Supporting Actor, along with a Golden Globe and a BAFTA Award. The performance was praised for its depth and authenticity, dominating the film. Del Toro’s win made him the third Puerto Rican actor to receive an Oscar.

‘Snatch’ (2000)

In Guy Ritchie’s stylish crime-comedy, Del Toro played Franky “Four Fingers,” a diamond thief with a gambling problem. The film features a large ensemble cast and a complex, twisting plot involving a stolen diamond and the world of underground boxing. Franky’s story is a key element that sets the chaotic events of the movie in motion.

Though his screen time is limited, Del Toro’s character is central to the narrative and is frequently mentioned by other characters. His role as the ill-fated diamond thief added to his growing list of memorable and quirky characters in popular films. ‘Snatch’ became a cult hit, known for its fast-paced editing and dark humor.

’21 Grams’ (2003)

Del Toro received his second Academy Award nomination for his role as Jack Jordan, an ex-convict who finds religion. The film uses a non-linear narrative to tell the story of three individuals whose lives are connected by a tragic car accident. Del Toro’s character struggles with guilt and faith after the event.

His performance was widely praised by critics for its emotional intensity and complexity. He co-starred with Sean Penn and Naomi Watts, and all three actors received Oscar nominations for their roles. The film was recognized for its powerful storytelling and raw, emotional performances.

‘Sin City’ (2005)

In this visually distinct film based on Frank Miller’s graphic novels, Del Toro played Detective Lieutenant Jack “Jackie Boy” Rafferty. The movie is shot in black and white with selective use of color, recreating the look of the source material. Jackie Boy is a corrupt and abusive police officer who meets a violent end.

The film was a critical and commercial success, praised for its unique visual style and faithful adaptation of the comics. Del Toro’s character was part of one of the film’s main segments, and his menacing performance contributed to the dark and gritty tone of the movie.

‘Che’ (2008)

Del Toro took on the lead role of revolutionary Che Guevara in this two-part biographical film directed by Steven Soderbergh. The film covers Guevara’s involvement in the Cuban Revolution and his later attempt to start an uprising in Bolivia. Del Toro, who also served as a producer, spent years researching the historical figure.

His dedicated portrayal earned him the Best Actor award at the Cannes Film Festival. The film was praised for its ambitious scope and Del Toro’s immersive performance, which captured the iconic figure’s determination and ideals. It was a significant project that showcased his ability to carry a major historical epic.

‘Sicario’ (2015)

Del Toro played Alejandro Gillick, a mysterious and vengeful former prosecutor working with a U.S. government task force to fight a Mexican drug cartel. The film follows an idealistic FBI agent who is drawn into the brutal and morally ambiguous world of the war on drugs. Alejandro is a quiet but deadly figure with a tragic past.

The film received critical acclaim for its intense action, direction, and the performances of its cast. Del Toro’s portrayal of the enigmatic hitman was singled out for praise and became one of his most recognized roles. He later reprised the role in the sequel, ‘Sicario: Day of the Soldado’.

‘Star Wars: The Last Jedi’ (2017)

Del Toro joined another major franchise with his role as DJ, a cynical codebreaker, or “slicer.” Finn and Rose meet him in a jail cell on the casino planet of Canto Bight. His character’s motto is “Don’t Join,” reflecting his belief that both the First Order and the Resistance are part of a corrupt system.

DJ is a morally ambiguous character who ultimately betrays the heroes to save himself. Del Toro’s performance added an unpredictable element to the film, showing a character who operates purely out of self-interest in a galaxy defined by its clear-cut battles between good and evil. His character provided a unique perspective within the ‘Star Wars’ universe.

‘The French Dispatch’ (2021)

In his first collaboration with director Wes Anderson, Del Toro played Moses Rosenthaler, a mentally disturbed artist who is serving a life sentence in prison. The film is an anthology of stories from the final issue of a fictional magazine. Rosenthaler’s story is one of the central segments, focusing on his art, his muse, and a greedy art dealer.

The film features Anderson’s signature visual style and a large ensemble cast. Del Toro’s performance as the intense and brilliant artist was a key part of his segment, where he worked alongside actors like Tilda Swinton, Adrien Brody, and Léa Seydoux. His character was noted as being one of the first explicitly Jewish main characters in a Wes Anderson film.

‘Reptile’ (2023)

Del Toro starred as Detective Tom Nichols, a hardened detective investigating the brutal murder of a young real estate agent. He also co-wrote and served as an executive producer on the film. The crime thriller follows Nichols as he uncovers a complex web of deceit and corruption that blurs the lines of his case.

The film explores themes of illusion and reality, with Del Toro’s character navigating a case where nothing is as it seems. His involvement behind the scenes as a writer and producer demonstrated his growing influence in filmmaking, in addition to his leading role in front of the camera.

‘The Phoenician Scheme’ (2025)

Del Toro reunites with director Wes Anderson for this espionage black-comedy. He stars as Anatole “Zsa-zsa” Korda, a charismatic and ruthless business tycoon. The film follows Korda as he names his daughter, a nun, as the heir to his vast estate, leading to a series of comedic and dangerous events.

The movie is described as a dark espionage tale with a father-daughter relationship at its core. It features another large ensemble cast, a signature of Anderson’s films, including Michael Cera, Mia Threapleton, and Tom Hanks. Del Toro’s lead role marks a significant collaboration with the acclaimed director.

Which of Benicio Del Toro’s many roles has been your absolute favorite?