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He’ll Flip You for Real: The Mysterious Genius of Benicio Del Toro

The star of the summer’s most unlikely sequel ‘Sicario: Day of the Soldado’ is one of the world’s greatest actors. Should he be a bigger star?

Getty Images/Ringer illustration

Benicio Del Toro loves McCartney II. And he has an encyclopedic knowledge of off-brand Rolling Stones albums. (Basically, anything released after Tattoo You.) Just ask him. He talks about his vintage record collection constantly with reporters. Read any profile of one of the most compelling (and yet also weirdly unheralded) actors of the past 30 years—now starring in the summer’s unlikeliest franchise film, Sicario: Day of the Soldado—and you’ll inevitably bump up against classic-rock ephemera. As far as journalists are concerned, Del Toro’s Rosebud is a beat-up copy of The Trouser Press Record Guide.

For instance: In 2007, Del Toro spoke to Esquire right before shipping off to the exhausting shoot for Steven Soderbergh’s four-hour epic Che, which Del Toro also produced. A biopic about the life of Argentine revolutionary and Fidel Castro sidekick Ernesto “Che” Guevara had been Del Toro’s passion project for nearly two decades, ever since he picked up one of Guevara’s books while filming the 1989 James Bond film License to Kill in Mexico City. (Kill was his second film, after 1988’s Big Top Pee-wee, in which he plays Duke, the Dog-Faced Boy, a reliable source of fodder for talk-show appearances for years to come.)

In the Esquire article, Del Toro openly stresses about the anticipated rigors of Che, and the impact the film’s success or failure will have on his career. “This will be the sort of aria that defines him, that confirms him as one of film’s great men, or that ruins him. And all of this, every last scrap of it, he knows,” intones writer Chris Jones—a little melodramatic, perhaps, but also prophetic.

“I can’t fucking fuck around,” Del Toro, cutting to the chase, announces.

Spoiler alert: Che wasn’t a hit, commercially or critically. But it only ruined Del Toro in the sense that he didn’t enter that rarefied strata of leading men with prestige, with Denzel, George, and the Toms (Hanks and Cruise). If you’re curious, as I am, as to why Del Toro never ended up on that level—Day of the Soldado is only the second big-time summer film he’s ever headlined—in spite of his considerable gifts and charisma, Che seems like the most obvious place to start.

Benicio Del Toro in ‘Che’
Courtesy of Warner Bros.

As it turned out, Soderbergh and Del Toro didn’t make the sort of historical blockbuster that wins Academy Awards and entices audiences to theaters during the holiday season. Che is more like a comment on awards-bait period pieces, pondering the humdrum realities of running a guerilla uprising and how difficult it can be to top yourself later in life, when you’ve already toppled a government, without the benefit of swelling orchestral accents or tidy, satisfying plot conventions. It’s a dry, emotionally distant film with a lived-in, unshowy, deeply internalized performance at its center. In terms of giving audiences what they expect, Soderbergh and Del Toro actually did fuck around on Che.

“We’re trying not to do Che’s greatest hits,” Del Toro explained to Esquire before filming. “If you’re doing a greatest hits of the Rolling Stones, you probably open up with ‘Satisfaction’ and you finish the first side of the album with ‘Sympathy for the Devil,’ and then you open Side 2 with ‘Gimme Shelter’ and you close with ‘Start Me Up.’ Well, we’re trying to start with ‘Blue Turns to Grey’ and finish with ‘Stray Cat Blues,’ and then start the second side with ‘Luxury’ and finish it with ‘Infamy,’ something like that.”

“Infamy”? I pride myself on knowing the ins and outs of zero-tier Stones records, and even I had to Google that Keef-sung deep cut from A Bigger Bang. It’s totally appropriate as a metaphor for the obscurity of Che.

The media has long focused on Del Toro’s fascination with the past (particularly the ’70s) as a sign of his timeless, effortless cool. A 2018 story in the British edition of Esquire, timed to the release of Day of the Soldado, dwelled on his love of old male actors (De Niro, Nicholson, Hoffman), his old Ford LTD, and, of course, old rock bands.

“I go, ‘What you been doing?’ He goes, ‘I’ve been watching old movies.’ I go, ‘That’s what you did yesterday?’ He goes, ‘No, that’s what I did for the last month.’ And I know that he means it,” Josh Brolin, his Day of the Soldado costar, told Esquire. “He’s literally been in the dark for 30 days, just watching old movies and eating Doritos.”

It’s a funny anecdote, but I feel like it also explains Benicio Del Toro perfectly.

It’s one thing to live in the past. But Del Toro seems like a man from the past who is mistakenly living in the modern world. He’s not figuratively John Cazale with Al Pacino’s face, he truly is a guy who should’ve been making movies with Sidney Lumet and Michael Cimino in 1974. Because that’s where he belongs. I think he’s obsessed with McCartney’s “Temporary Secretary” because it’s an artifact from home. It’s like the scene in E.T. in which the alien desperately reaches out to the kid in the Yoda Halloween costume. Del Toro is similarly seeking familiar comforts in an utterly foreign world.

I’ll always believe that Benicio Del Toro somehow mistakenly slipped through a tear in the space-time continuum, and washed up in the crushingly ungroovy wasteland that was the 1980s, when he first started striving to make his ’70s-style arthouse historical drama while playing the role of Dario, an evil henchman out for Timothy Dalton’s head who is eventually shredded to death. Since then, he’s remained a laconic figure, the midnight rambler, forever stumbling in vain through the present, darkly.

Let’s state the obvious: Day of the Soldado doesn’t need to exist. The first Sicario movie ended more or less perfectly. And it wasn’t much of a hit. It’s reasonable to ponder this movie solely as a manifestation of Hollywood’s addiction to franchises, another installment in a summer of sequels that nobody asked for.

But for those who feel that revisiting the sight of Josh Brolin in flip-flops is justification enough—admittedly, I’m in this camp—a different view of Day of the Soldado is equally valid. This is an uncommonly bleak film that’s relevant to current events (particularly the fraught state of the U.S.-Mexico border) and cynical about the moral acuity of the government and authority figures in general. Not only are the heroes in this movie resolutely not super, they barely register as heroic.

Nobody will mistake what’s essentially a brawny action film for The Parallax View or The Conversation. But Day of the Soldado has an unsettled rage at its core that resonates in America’s darkest periods, whether it’s post-Watergate or the age of Trump. It feels like a movie that was made for adults, at least relative to other blockbuster fare this summer.

In the first Sicario, much of the film is told from the perspective of Kate Macer (Emily Blunt), an FBI agent who is ultimately played by domineering Department of Justice operative Matt Graver (Brolin). In the film’s closing third, the point of view shifts to Graver and especially Alejandro Gillick, a mysterious killer-for-hire played by Del Toro. But Day of the Soldado dispenses with Blunt altogether, leaving only Brolin, Del Toro, and a gaping moral void.

Del Toto in ‘Sicario’

Del Toro has made a career out of stealing movies from higher-billed actors—The Usual Suspects, Fear and Loathing in Las Vegas, even Traffic. But Taylor Sheridan’s screenplay for Sicario made this theft integral to the story, with Gillick acting as a kind of Grim Reaper figure wielding a creeping darkness that eventually swallows the film. (Del Toro wasn’t sure this shift would work until he actually saw the movie.) After seeing Day of the Soldado, I question whether Blunt’s character’s absence from the second film was a good idea, as this universe is now completely amoral. There’s nobody to signal to the audience that what Brolin and Del Toro’s characters do in this movie—no spoilers, but it’s a whole other level of despicable—is intended to be viewed as “bad” by the audience. The ambiguity at times feels a bit imprecise.

All we have are Del Toro’s eyes. They are the film’s ballast, giving one reason to describe Gillick as “sympathetic,” even if there’s little else to support such an assertion. There’s torment in those eyes, and immense sorrow, and even unexpected kindness. They are windows into the movie’s tortured heart.

In another time, Lee Marvin would’ve played Gillick, a professional killer who approaches his job with the workaday weariness of a traveling salesman. Marvin’s brand of wounded, taciturn masculinity is now virtually extinct from modern action movies. There’s some Steve McQueen from The Getaway in Gillick, too, in that Del Toro doesn’t have to say much to tell his story. He expresses it with the way he holds a gun, and stares out a window, and contemplates a young woman who reminds him of his daughter.

Marvin and McQueen have long since departed. But Del Toro, for our sake, was left behind.

The first summer film that Del Toro starred in, Excess Baggage, was released 21 years ago. It was not, shall we say, a success, either in the moment or in retrospect. A generic Gen X crime comedy, right down to the requisite “kooky” supporting role for Christopher Walken, Excess Baggage costars Alicia Silverstone, who played Batgirl in one of the most notorious disasters in Hollywood history, Batman & Robin, just two months prior. On the soundtrack, “Crash Into Me” by Dave Matthews Band and “One Headlight” by the Wallflowers have prominent placements. It might very well be the most 1997 movie released in 1997.

Del Toro turned 30 that year. That he was in Hollywood at all was due to both a stroke of bad fortune, and an incredibly generous and advantageous opportunity. As a boy, he grew up outside of San Juan in Puerto Rico, the youngest son of two lawyers and part of an extended family that included many members involved in law enforcement. At age 9, his mother died, sending him into a deep depression that he coped with by blowing off schoolwork and cracking wise in class.

When Del Toro was 13, his godmother Sarah, a prosperous attorney, offered a lifeline: If he wanted to transfer to a boarding school in Pennsylvania, she would help out. That same day, he boarded a plane with his father for America.

As a young man, Del Toro did a killer Mick Jagger impression, so good that one day his brother Gustavo suggested he try acting. At the University of California–San Diego, he majored in business but gravitated to the school’s drama department. After just one year, he quit school and went to New York, ready to become the next Marlon Brando. Instead, he returned home chastened after just five months, wound up in L.A., and connected with the iconic acting teacher who had trained Brando, Stella Adler.

Del Toro started popping up in small roles not long after that, mostly in television dramas that called for young Puerto Ricans who could conform to a TV writer’s idea of a young, criminally minded punk. While Del Toro now cuts a glamorously weathered, everyman figure, he had a striking beauty as a young man that was almost feminine. And he carried himself like a man who fully owned that beauty. In the video for 1986’s “La Isla Bonita”—you see him briefly around the 3:35 mark—he already had the nerve to flirt with Madonna, making eyes at her while seated on the hood of a car as she sashayed past him.

Del Toro met Brolin for the first time around then, on the set of the short-lived “cops in ’50s L.A.” NBC drama Private Eye. “He was really skinny, had a big tuft of hair on his head that went straight out, like Eraserhead,” Brolin recalled to Esquire.

Their big scene involved a stolen car, a ’49 Merc, that belonged to Brolin’s character, the awesomely named Johnny Betts. “He had this one line: ‘Don’t ever come back here again,’” Brolin said. “And this was how he did it: ‘Don’t ever … come back … here … again.’ And I was like, ‘This motherfucker is taking so long to say this line.’ Like, ‘How is he stretching this out as long as he is?’ He fucking stole the scene, man. He killed it. He was wonderful.”

Del Toro in ‘The Usual Suspects’
Getty Images

Flash forward several years, to the mid-’90s, when Del Toro is making The Usual Suspects and trying to steal a much bigger prize. Cast as Fred Fenster, Del Toro knew after reading the script that he was saddled with a nothing role, as his character is swiftly dispensed by arch villain Keyser Soze about 40 minutes into the film. He had to find a way to stand out. Inspired by Timothy Carey’s clenched-jaw mannerisms in Stanley Kubrick’s The Killing, a key precursor to The Usual Suspects in so many ways, Del Toro turned Fenster into a flamboyant peacock with impeccably plucked eyebrows and an indecipherable speech impediment.

It was a risk, and Del Toro panicked during filming that he was making a fool of himself. But the end result was a repeat of the Private Eye experience, only on a much bigger scale. He didn’t have many lines, but what he delivered—“He’ll flip you, flip you for real!” and “Is that the one about the hooker with dysentery?” and “Hand me the fuckin’ keys you cocksucker, what the fuck?”—was laugh-out-loud funny and singularly bizarre. Even in a film stacked with an all-time cast of stellar character actors, Del Toro’s star quality was undeniable.

A traditional heist film filtered through a post–Reservoir Dogs, New Hollywood–inspired lens, the preferred mode of so many indie hits of the time, The Usual Suspects was an ideal and not easily replicable showcase for Del Toro’s talents and sensibility. Which brings us back to Excess Baggage, in which you can see Del Toro try to incorporate the same quirky character flourishes from his breakthrough.

His accent in Excess Baggage, while not as extreme as it is in The Usual Suspects, is still a bit of a head-scratcher—a little Noo Yawk Italian, a touch of Cheech & Chong, a pinch of Charles Bronson. His hair is grown out into a curly shag, kind of like Yield-era Eddie Vedder, bringing out the delicacy of his cheekbones.

He looked great, but while the size of his role had grown, he had even less to do than in The Usual Suspects. And his love interest was the star from Clueless, which was jarring. Silverstone belonged to “the ’90s,” an era-specific concept signified by Friends, boxy blazers and baggy jeans, and that trio of videos that Silverstone starred in from Aerosmith’s Get a Grip. Del Toro became a star in the decade but he wasn’t part of that ’90s. He wasn’t “Crazy” or “Amazing,” he was “Sweet Emotion,” aligned with the Down and Dirty Pictures crowd that not-so-secretly wished it had been part of the Easy Riders, Raging Bulls decade.

As the most ’70s-like decade to happen in cinema since the actual ’70s, working in the ’90s still had to feel like a consolation prize for Del Toro, a classic rocker trapped in a grunge epoch. The films he made that people remember from this time are the ones most analogous to Stones albums. His performance in The Usual Suspects was Aftermath, hilarious and dark and decadent. Fear and Loathing in Las Vegas is his Goats Head Soup, debauched and melancholy, a wave breaking and rolling back. The Way of the Gun, his underrated reunion with Usual Suspects screenwriter Christopher McQuarrie, is Undercover, violent and angry and coked out.

Behind the scenes, he developed a reputation as a rabble rouser, a potential crash-and-burn cautionary tale. A Rolling Stone check-in during the filming of Fear and Loathing in Las Vegas features some predictably unhinged scenes involving Del Toro engaged in surreal, drug-and-booze-fueled escapades with the film’s subject, Hunter S. Thompson. At one point, Thompson smears lipstick across his face while he and Del Toro watch baseball and swill whiskey.

“Want some?” Thompson asks Del Toro, offering the lipstick, and soon Del Toro is also covered in red.

If life was a little hazy off the screen, Del Toro could also be a blurry presence on screen—his face obscured, his voice garbled, his mannerisms difficult to discern. He wasn’t acting, he was doing something rarer and harder to define. He was transforming himself, beyond characters and into an ineffable presence that glided through his movies. He was a vibe.

Something shifted for Del Toro in the early ’00s—he no longer had to steal scenes or entire movies wholesale. He was now being handed the sort of respectable parts that earned him widespread acclaim as a matter of course. In the first half of the decade, he was nominated twice for a Best Supporting Actor Oscar, and won once, for Traffic, in which he is called upon to be the film’s moral compass. This was just a few years after getting wasted with Hunter S. Thompson on the set of Fear and Loathing in Las Vegas. Waves break funny sometimes.

Traffic is still the highest-grossing, non-Marvel, non–Star Wars movie that Del Toro has made. It will likely be the first film mentioned in his obituary, but though he’s very good in it, it isn’t among the first six or seven films I like to revisit when I want to watch him. (I even prefer The Hunted, William Friedkin’s minimalist 2003 thriller, in which Del Toro plays a kind of real-life, naturalistic Rambo.) This has almost nothing to do with Del Toro, but rather what surrounds Del Toro. His story, about a Mexican cop who learns to exploit the corruption he sees on all sides of the drug war in the service of performing a small but vital good deed for his community, is so much better than the other narratives that it undermines the rest of the movie.

I don’t care about Michael Douglas bantering with Orrin Hatch, or Erika Christensen freebasing with Topher Grace. When I watch Traffic, I always skip ahead to Del Toro talking about night baseball with those DEA agents in the swimming pool. That was Del Toro’s brainstorm, by the way. It was yet another way for Del Toro to stand out in a film overcrowded with great actors, filming a critical scene in an irregular way, though he was now confident enough to play down the affectations in his characters.

In 2003’s 21 Grams, which garnered him his second Oscar nomination, he goes full-on “Brando in Last Tango in Paris,” internalizing an agonizing level of psychic pain in the role of an ex-con-turned-born-again-Christian who absorbs immense personal tragedy on a Job-like scale. The second film by director Alejandro González Iñárritu, and the second part of his convoluted “death trilogy” made in collaboration with screenwriter Guillermo Arriaga, 21 Grams is a grim actors showcase, an excuse for Del Toro and costars Sean Penn and Naomi Watts to emote with maximum velocity. It’s a little, well, much, though Iñárritu’s tendency to grandstand inspires Del Toro to pull back even further into himself. By now, there was no more hiding behind eccentric accents or colorful costumes—his suffering in 21 Grams is crystal, unbearably clear.

The pensive, troubled tough guys that Del Toro plays in Traffic and 21 Grams are precursors to the spiritually wounded Alejandro Gillick, who can point a gun at Emily Blunt’s head without losing the warm, paternalistic lilt in his voice. Del Toro no longer had to transform into a presence on screen, he could just be one.

The problem is that there was a 12-year gap between 21 Grams and Sicario. The second half of the ’00s and the early part of the ’10s is Del Toro’s wilderness period, the dip between Exile on Main Street and Some Girls, when he seemed to drift away from the public consciousness. After the disappointment of Che in 2008, he made 2010’s The Wolfman, a project that attracted him because of his boyhood interest in monster movies. (He was also a producer on the film.) But The Wolfman wasn’t a stark, shadowy creeper evoking the spirit of ’30s Hollywood, it was an elaborate yet anonymous $150 million bomb that swiftly sank into obscurity that February, the annual dead zone on the cinematic calendar.

He failed with his prestige project. He failed with his big-budget horror blockbuster. Del Toro had to start over. In the process, he reached a detente with time.

In 1978, Marlon Brando played Jor-El in Superman. The following year, he was Colonel Kurtz in Apocalypse Now. And yet in both movies, Brando was really Brando—the embodiment of inscrutable, ridiculous, and unbeatable magnetism.

Del Toro has achieved a similar balance in the past five years, working at the center of Hollywood as well as on the fringes. As the Collector, he earned his meal ticket in the Marvel Cinematic Universe without selling his soul. When you see him pop up in Thor: The Dark World, Guardians of the Galaxy or Avengers: Infinity War, with a shock of white hair that makes him looks like Jim Jarmusch rolling into Comic Con, or as the rakish DJ in Star Wars: The Last Jedi, you suspect that he’s gently laughing to himself, as if to say, How did a kid from San Germán end up here? But he never succumbs to the implied eyerolls that Brando drops throughout his extended Superman cameo. He plays it close to the vest, and with surprising reverence, like always.

The same year that Del Toro slipped in a subtle Stranger Than Paradise flavor to Guardians of the Galaxy, he gave one of my favorite performances of his career in Inherent Vice, a movie I could watch every single day and never tire of. Here Del Toro could finally feel at home—he was with Paul Thomas Anderson, a ’90s-bred New Hollywood disciple, and set loose in L.A. in the year between Let It Bleed and Sticky Fingers. Perhaps that’s why, more than any other movie, he talks, moves, laughs, inhales, and exhales like a warm, inviting man who closely resembles Benicio Del Toro. I have no idea what he is like in real life, but I choose to believe that he is essentially Sauncho Smilax, a man who playfully banters about soulful boats, old Hollywood conspiracies, and systemic political malfeasance over beer-battered Del Rey filet and a few tall tequila zombies.

Because he’s one of my favorite actors, I sometimes wish Benicio Del Toro had reached that Denzel strata. Though if that had happened, he might’ve ended up like his Fear and Loathing costar Johnny Depp, a victim of rock ’n’ roll fantasies fueled by bloated-yet-still-dwindling coffers.

This is the better timeline. Like Mick and Macca, he’s hitting a different kind of stride in his 50s, that of a survivor with some mileage on his tires who is constantly trucking forward, secure in the knowledge that he has it—skill, swagger, spirit, soulfulness—and always will.