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From Tyler Durden to Cliff Booth: Brad Pitt’s coolest roles

If Brad Pitt hadn’t been so judicious in choosing roles, it’s likely he wouldn’t have stayed on top of the movie star game for the last 30 years, a sustained run of success that few have rivaled in the post-movie star age. If we consider stars who have faded out of movie stardom — or faded out and back in (sometimes more than once) — like Bruce Willis or John Travolta or Eddie Murphy, it’s usually because they are no longer perceived as cool, when their choice of roles makes them seem silly or desperate or has-been.

Pitt has avoided this for over three decades. Among his contemporaries, perhaps only Tom Hanks has had a longer run of sustained movie star relevance, and even Hanks wasn’t looking so cool in the era between Big and A League of Their Own. (Remember Punchline?) So how does Pitt do it? It’s all about the roles, baby — an actor realizing exactly what makes his image appealing. As Pitt returns his brand of cool to the big screen in Bullet Train, we assess some of his coolest roles and how they have formed his legacy.

Thelma and Louise (1991) J.D.

Brad Pitt in Thelma and Louise.

Susan Sarandon and Geena Davis star in Ridley Scott’s feminist classic about two friends whose weekend of freedom and fun takes a dark turn when they kill a would-be rapist. Fearing they won’t be believed, the women decide to go on the run rather than turn themselves in, allowing Scott and screenwriter Callie Khouri to satirize the male road trip genre while criticizing toxic masculinity in its many insidious forms. As Thelma and Louise pass the point of return (through a beautifully shot American West), their odyssey becomes one of discovery, as well as an allegory about the cost to women who choose to defy society’s prescribed gender roles.

Pitt’s role as the criminal drifter J.D. is a small one, but it made him an instant star, and not just because he took his shirt off. His brief tryst with Thelma awakens her to the desires she has submerged in a controlling marriage. J.D. is a good listener, receptive to her needs, and a playful and attentive lover. He seems to realize that, above all, Thelma longs for someone to confide in and feel safe with. Pitt’s performance, in which he exudes boyish vulnerability while projecting cocky charm, became something of a template for his career, while making him a sex symbol for all time.

You can stream Thelma and Louise on HBO Max and stream and rent it on other digital platforms.

Kalifornia (1993) Early Grayce

Brad Pitt and Juliette Lewis in Kalifornia

If Thelma and Louise bestowed upon Pitt the reputation as a pretty boy, the harrowing Kalifornia — released just two years later — proved in no uncertain terms that the pretty boy could act. An entry in the road trip/crime spree subgenre inexplicably popular in the early ’90s (which included Thelma and Louise as well as True Romance, One False Move, and Natural Born Killers), the movie stars David Duchovny and Michelle Forbes as a broke young couple trying to get from New York to California. When they make the fateful decision to take on the white trash Early Grayce (Pitt) and his developmentally disabled girlfriend (Juliette Lewis, who plays much the same role in Natural Born Killers) for gas money, they get a serious education into how the other half lives. The Duchovny character, a writer who chronicles mass murderers, is initially intrigued by Earley’s dangerous energy until things go too far and the trip descends into hell.

So what’s “cool” about playing a psychopath who gets off on murder? The skill with which Pitt delivers the performance, for one thing, as well as the guts it took to make a film this bleak and disturbing just when his star was on the rise after a decade of toiling in television. Also, Kalifornia condemns not only violence itself, but the hypocrisy with which our society romanticizes and voraciously consumes it (and this was pre-Internet). Though the movie was not a hit, it found admirers, including Roger Ebert, who named it one of the year’s best movies and called Pitt’s performance “electrifying.”

You can stream Kalifornia on Direct TV and rent it on other digital platforms.

Fight Club (1999) Tyler Durden

Brad Pitt wearing red leather jacket in Fight Club
20th Century Studios

Incoherent at the level of both story and theme, David Fincher’s Fight Club is as schizophrenic as its protagonist (Edward Norton), a mentally ill young man who (spoiler) invents an alter ego, Tyler Durden (Pitt), that allows him to buck the conformity of his corporate yuppie existence and act out his every depraved antisocial fantasy — first in an underground fight club, and later as part of a domestic terror organization that targets, well, everything. Fincher and his writers (including Chuck Palahniuk, on whose novel the movie is based) can’t make up their mind which people and institutions are most deserving of their contempt. And so, like the deranged adolescent men at its center who feel that society has emasculated them, it lashes out brutally in every direction.

Fight Club is too scattered and witless to be a satire, and the less said about its irresponsible take on mental illness, the better. What remains is a shockingly misogynistic and homophobic fantasy, the likes of which has become all too familiar in the two decades since it became a cult classic. It’s disquieting to consider the influence this movie may have had on legions of angry, paranoid young men who revel in its nihilism and believe it to be some kind of manifesto that equates anarchy with virility.

Brad Pitt shirtless in Fight Club
20th Century Studios

And yet (deep breath!), Fight Club is well directed and conceived by Fincher at the level of production design and world building. Pitt and Norton are excellent, delivering the reams of narration and dialogue from the novel in convincing fashion, as well as giving the movie the slithery physicality that drives it. Confident, possessed of inhuman abs, and rocking some of the grooviest threads this side of ’70s glam rock — including his now legendary red leather jacket — Pitt’s coolness in Fight Club is thrilling. You just have to sit through a moral catastrophe to witness it.

You can rent Fight Club on Apple TV and other digital platforms. 

Inglourious Basterds (2009) Lt. Aldo Raine

Brad Pitt in Inglourious Basterds
Universal Pictures

I can imagine how the pitch went on this one.

Quentin Tarantino: I want to make a 2 1/2 hour movie about classic European cinema with lots of subtitles and a sadistic SS officer as one of the main characters.

Studio Execs: Absolutely not!

Tarantino: Brad Pitt has signed on.

Studio Execs: When can you start production?

Because, let’s face it, Pitt has been one of the few 21st century movie stars who can put butts in seats because of his name and not because he’s wearing a cape and cowl or wielding a wand or lightsaber. Tarantino rewarded the actor’s participation by giving him the scenery-chewing role of the Tennessee-born Lt. Aldo Raine, leader of the Basterds, enthusiastic mutilators of Nazis (or, as Raine calls them, “Nat-zees”) who get a chance to help end World War II by pulling off a hellacious act of sabotage, which, despite its logistical difficulty, still proves more achievable than Raine speaking Italian with a Tennessee accent.

If Fight Club seems more than ever like the fantasy of juvenile masochists, Inglourious Basterds — despite also gleefully reveling in violence — seems even more elegant and sophisticated. Much of this has to do with the formal beauty of Tarantino’s filmmaking: the lush production design and elaborate but understated cinematography. The way the director allows suspense to build over long sequences in this movie is worthy of Hitchcock, and not just the famous scenes set in the farmhouse or the pub basement, but even when the heroine (Mélanie Laurent) is forced to endure coffee and strudel with the monster (Christoph Waltz in an Oscar-winning part) that massacred her family. Check out Pitt and company on the gorgeous 4K UHD Blu-Ray if you get a chance.

You can stream Inglourious Basterds on Direct TV and other digital platforms.

Once Upon a Time in Hollywood (2019) Cliff Booth

Brad Pitt and Leo Decaprio in OUATIH
Sony Pictures

This light fantasy is about two buddies, Rick Dalton (Leonardo DiCaprio), a fading TV star struggling for relevance, and his stuntman Cliff Booth, who — having given up his own aspirations of stardom — is just trying to ride his friend’s coattails for as long as it will last. Tarantino, merchant of cool, knows exactly how to present Pitt in this movie, giving him swell (if controversial) moments like fighting Bruce Lee while wearing a tuxedo and buzzing around in a convertible Volkswagen Karmann Ghia.

After Inglorious Basterds and Django Unchained, Once Upon a Time… In Hollywood was Tarantino’s third (and hopefully last, as these things do run their course) revisionist history that imagines evil men getting their violent comeuppance at the hands of worthy heroes. The evil man in this one is Charles Manson, and he’s got, like, a super downer vibe that in this world is far more responsible for the problems of late 1960s Los Angeles than, say, institutionalized racism, pollution, massive income inequality, or a war that’s tearing the country apart. But, hey, I’m harshing the buzz by even addressing such things.

Booth, more than the anxious Dalton, becomes the ideal embodiment of Tarantino’s vision of Los Angeles as a laid-back utopia, which could maintain its untroubled aura forever if it just purged ungroovy dudes like Manson and his ilk. The Hollywood standard-bearers (whose job, after all, is to maintain crumbling L.A.’s Edenic facade) seemed to agree with this formulation, as Pitt won an Oscar and numerous other accolades for his performance.

You can stream Once Upon a Time in Hollywood on FuboTV and rent it on other digital platforms.

The Lost City (2022) – Jack Trainer

Brad Pitt in The Lost City

After all the serial killing, bloody pugilism, moral depravity, and Nazi mutilation, we had better end on a fun one. One thing that has kept Pitt on top all these years is that he understands that less is more when it comes to film appearances. Especially as somebody who gets his mug crammed into the public consciousness at every moment in celebrity news, the actor makes sure to not oversaturate his presence in the movies. Part of this approach has been to toggle back and forth between playing the lead and taking supporting parts or to join a talented ensemble in gigs such as Once Upon a Time… In Hollywood, 12 Years a Slave (which he also produced), or The Big Short.

These supporting parts are sometimes in comedies in which he lampoons his image, such as the Coen Brothers’ Burn After Reading or The Lost City, the romantic fluff starring Sandra Bullock as a romance author who becomes embroiled in one of her own melodramatic plots alongside the cover model from her novels (Channing Tatum).

Pitt plays a small role as Jack Trainer, one of these special-ops fighter assassin martial arts experts that are so common in the movies (yet somehow rare in real life) who gets called in to help rescue the Bullock character from the clutches of a megalomaniac (Daniel Radcliffe, surprisingly effective as a villain). Pitt’s screen time is brief, but the movie makes the most of it. The actor makes fun of action heroes in The Lost City, while simultaneously playing a badass himself, which sort of sums up the secret of his success as the ultimate cool guy in the movies.

You can stream The Lost City on Paramount + and other digital platforms.

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Michael Green
Michael Green is a writer and teacher who lives in Tempe, Arizona. His work has appeared in numerous publications including…
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