Once Upon a Time in Hollywood is Leonardo DiCaprio's — not Brad Pitt's — masterpiece (2023)

Once Upon a Time in Hollywood is Leonardo DiCaprio's — not Brad Pitt's —masterpiece (1)

(Once Upon a Time in Hollywood spoilers to follow)

“It’s the day in the life of a man sort of going not only through an emotional breakdown and a transition in his career, but a realization that time has sort of passed him by, that culture has passed him by.” — Leonardo DiCaprio on Rick Dalton.

“It’s official, old buddy. I’m a has-been.” Rick Dalton on Rick Dalton.

I can’t imagine Leonardo DiCaprio was capable of relating to the plight of Rick Dalton. By that, I don’t mean that Leo failed to sympathize with Rick’s struggle. I have no doubt that he did feel for Rick and that he incorporated sympathy into his work to maximize the effectiveness of his performance. I’d even go so far as to wager that Leo’s greatest fear was once becoming Rick, a TV actor who failed to make the leap to movies and has since been reduced to playing guest parts on TV shows, and then had the audacity to go get married to someone roughly his own age. But I don’t think Leo could really understand the struggles that Rick endures during Once Upon a Time in Hollywood, Quentin Tarantino’s ninth film that hit theaters this past summer and has held up on countless rewatches in the months since. The only traits that Leo and Rick share are their professions, their looks, and their friendships with Brad Pitt. The similarities stop there.

For one, Rick mostly failed to transition from TV to movies, while Leo did successfully make the leap from TV (Growing Pains) to movies. He’s arguably the biggest movie star on the planet and has been ever since he sacrificed himself to frigid waters for Kate Winslet way back in 1997. He’s regarded as one of the best actors in Hollywood, having won a Best Actor Academy Award in 2016. He’s at the stage in his career where he can pick and choose his projects, and even take a four-year hiatus from movies — as he did between The Revenant and Once Upon a Time in Hollywood — and reemerge with one of the biggest original films of the year that has both commercial and critical appeal. Twenty-six years ago, he was nominated for his first of six acting Oscars. Four years ago, he captured his first Oscar win for The Revenant. This past year, he worked with Tarantino on one of the best films of the year — by my estimation, it was the best film of the year, with all due respect to Parasite — and garnered his sixth Oscar nomination as a reward. He’s now been nominated for or won an Oscar for each of his past three movies and four of his past five. To facilitate the production of Once Upon a Time in Hollywood, he took a 50 percent pay cut, and he still hauled in $10 million for his services. Leo, 45, does not need to worry about ever becoming Rick. Becoming Rick might be his worst nightmare, but he’s everything Rick dreams of becoming.

Two, Rick married an actress named FrancescaCapucci, who appears to be over the age of 25. Leo, on the other hand, not so much.

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(H/T TrustLittleBrother)

Leo might not have been able to relate to Rick, but the good news is that (1) he’s an actor, which means it’s his job to pretend to be someone else even if he can’t relate to that person, and (2) he’s really darn good at it — as his filmography, box office receipts, and long list of accolades so clearly demonstrate. He’s especially good as Rick. He’s so good that I think it’s his best-ever performance — even better than his Oscar-winning performance in The Revenant (overrated) and other well-regarded performances in movies like The Wolf of Wall Street, The Departed, Blood Diamond, The Aviator, Shutter Island, Catch Me If You Can, Titanic (still great, don’t @ me), and What’s Eating Gilbert Grape, to name only some of his iconic performances.

Once Upon a Time in Hollywood is his masterpiece.

Once Upon a Time in Hollywood got nominated for 10 Oscars. It won two: Best Production Design and Best Supporting Actor. Leo as Rick was nominated for Best Actor, but lost to Joaquin Phoenix as Joker in Joker. Brad Pitt as Rick’s stunt double, Cliff Booth, won for Best Supporting Actor, marking his first-ever acting Oscar. It was long overdue.


The Academy Awards are dumb for a number of reasons, but chief among them is how it often refuses to recognize actors and directors for their best work before eventually rewarding them years down the line for something else because it suddenly decides that it’s their time to win. It’s less of a merit-based system and more of a wait-your-turn system.

It’s why Martin Scorsese finally won Best Director for The Departed in 2007 — not because The Departed is his best work, but because the Academy decided it was his turn to win. The same goes for Brad, who really deserved to win for his performance in Moneyball over the dude from The Artist, and Leo, who finally won Best Actor for The Revenant in 2016 but really deserved to win for *insert most of the movies Leo did between 2002-13*. It’s why I’ll be shocked if Tarantino doesn’t win his first Best Director Oscar for his eventual 10th and (what he says will be) his final movie. And it’s why Joaquin won at this year’s Academy Awards while Leo’s performance went virtually undiscussed. It was Joaquin’s turn. Leo already got his. You’re free to think Joaquin’s twisted performance as Joker was superior to Leo’s as Rick, but the undeniable truth is that if Leo hadn’t already won for The Revenant, the race would’ve been far tighter than the runaway that we ended up getting.

Both Leo’s eventual loss and Brad’s inevitable win quickly became foregone conclusions during #OscarSzn, long before the actual ceremony was held. Sure enough, on February 9, the results held. As such, even though every Tarantino movie will forever be known as a Tarantino movie rather any one actor’s movie, it’s become Brad’s ultimate triumph. In the minds of many, it is his — to borrow a phrase from The Rewatchables podcastapex mountain.

I’ll admit that when I saw Once Upon a Time in Hollywood on opening night — my first of five viewings in theaters — I thought Brad won the movie, even though Leo has long been my favorite actor.

It’s not difficult to understand why so many people, the Academy, and even me on July 26th thought it was Brad’s movie. He oozes pure and absolute charisma as Cliff.

So much of his performance is just him driving a car through 1969 Hollywood (there’s a reason it won for Best Production Design), taking care of a very good dog named Brandy, talking at the TV, or standing shirtless on a roof. And it totally works. It isn’t boring. It makes you want to be there with him, hanging out, drinking beers, and smoking while he recalls the time he (allegedly) kicked Bruce Lee’s ass.

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He owns the explosive final act of the movie. Cliff fending off the Manson Family while tripping on an acid-dipped cigarette is maybe the funniest thing I’ve ever seen on screen. I think that’s why when I left the theater after my first viewing of Once Upon a Time in Hollywood, I couldn’t stop thinking of Brad’s performance, because Brad Pitt is the coolest dude ever and in Once Upon a Time in Hollywood, Brad Pitt plays Brad Pitt — or at the very least, the stuntman version of Brad Pitt. Cliff is told at one point that he’s “kind ofpretty for a stuntman.” Therein lies the only flaw of the movie: Brad Pitt is too good looking to be a stuntman.

But with each subsequent rewatch, the more I’ve realized that while Brad is mesmerizing and undeniably cool in Once Upon a Time in Hollywood, it’s not Brad’s movie. It’s Leo’s.

I’m not saying that to diminish Brad’s performance — he’s fucking fantastic. There’s not another movie star who is as effortlessly cool as Brad Pitt. In that sense, I’m not sure the movie works with anyone other than Brad Pitt as Cliff Booth. But in Once Upon a Time in Hollywood, Brad is coasting on movie-star charisma. He just has it. I imagine it’s effortless for him too. He just stands there, whips off his shirt, cracks open a beer, and lights a cigarette, and that’s enough to enrapture us. I don’t know how much acting he’s actually doing. He’s just being Brad Pitt.

Leo, meanwhile, is tasked with doing so much more as Rick. Leo’s performance is not as charismatic or as cool as Brad’s. It’s subtler. But it’s also more difficult. It’s more compelling.

Think of all the roles within the role that Leo is playing. In one movie, he has to …

  1. play an alcoholic actor in the midst of an existential crisis.

  2. play a convincing TV cowboy on Bounty Law.

  3. give a shambolic performance as the heavy on Lancer.

  4. give a great performance as the heavy on Lancer.

  5. play an alcoholic actor who has come to terms with the state of his career, but is still angry at the changing world around him.

And that list doesn’t even include the countless other roles that Leo is tasked with playing in brief moments — from an over-the-top, Nazi-slaying soldier in The 14 Fists of McCluskey to his small guest-spot on The FBI. Leo’s performance as Rick might not be as noticeable or loud as, say, his take on Jordan Belfort in The Wolf of Wall Street, but he’s doing more than playing one character here. He contains multitudes.

Meanwhile, Brad plays the cool guy who should be, but isn’t worried about his future — one that looks increasingly bleak as Rick’s career dwindles away. After all, a stunt double is only as valuable as the actor he’s doubling. Most people think he killed his wife. But Cliff seems unconcerned by his perception. He has his friend. He has his dog. He has his car. And that’s enough.

When Rick complains to Cliff that he’ll have to move to Italy to star in Spaghetti Westerns, Cliff doesn’t understand the problem. To Cliff, it’s a chance to go live in a cool foreign country while getting paid to make movies. What’s the problem? There is no problem.

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Rick is the opposite. Cliff is content with being a gofer, but Rick can’t stand the thought of starring in Italian Westerns. To him, it’s a death sentence.

Rick: “Five years of ascent. Ten years of treading water. And now a race to the bottom.”

Cliff: “Look, I’ve never had much of a career to speak of, so I can’t say I really know how you feel.”

Rick: “What’re you talking about? You’re my stunt double. Come on, now. Shit.”

Cliff: “Rick, I’m your driver, man. I’m your gofer. I’m not complaining, man. I like driving you around. I like doing shit around the house and house-sitting in the Hollywood Hills when you’re gone. But I haven’t been a full-time stuntman for a while now, and from where I’m standing, going to Rome to star in movies does not sound like the fate worse than death that you seem to think it is.”

Rick: “C’mon now. You ever seen an Italian western? They’re awful. It’s a fucking farce.”

Cliff: “Yeah. How many you’ve seen? One? Two?”

Rick: “I’ve seen enough, all right? Nobody likes Spaghetti Westerns.”

Once Upon a Time in Hollywood shows us two-and-a-half days in the lives of Rick, Cliff, and Sharon Tate — this is beside the point, but Margot Robbie is mesmerizing as Sharon Tate, and those who think her lack of dialogue is problematic are missing the entire point of her performance and role in the movie. In the first two of those two-and-a-half days, Rick is in the midst of a breakdown. He’s in crisis mode, having just been told by an agent (Al Pacino) that he needs to leave Hollywood for Italy if he wants to star in Westerns again. He’s realized that he’s a has-been and lost in a Hollywood that he no longer recognizes. It’s as unrecognizable to him as Rome. To make matters worse, he’s living next door to Sharon, an actress on a path leading toward superstardom, and her husband, Roman Polanski — at the time, one of the hottest directors in Hollywood (in real life, Polanski is no longer that).

The foundation of Leo’s performance is the actor in the midst of a breakdown. And he performs that role exceptionally. It’s most notable in that trailer breakdown scene, after he fucks up his lines on the show he’s guest-starring on as the heavy — a.k.a. the guy who gets his ass kicked by the star of the show — as he laments his decision to drink “eight fucking whiskey sours” while he practiced his lines the night before, because now no one is going to think he actually did practice his lines, but he really did practice his lines all night … while drinking eight fucking whiskey sours.


It’s a scene that Leo both pitched to Tarantino and improvised.

“It wasn’t in the script actually, so we never rehearsed it or anything,” Tarantino said. “Leo had a whole thing. At some point it was like, ‘Look, I need I need to fuck up during the Lancer sequence, all right? And when I fuck up during the Lancer sequence, I need to have a real crisis of conscience about it and that I have to come back from that.'”

It’s also one of the most memorable and rewatchable moments in a movie filled with memorable and rewatchable moments. More importantly, it’s entirely relatable — not just for Leo, an actor who has undoubtedly flubbed his lines at some point during his career, but for all of us sitting in the audience. I mean, who here can’t relate to a fuck up?

“Eight fucking whiskey sours? I couldn’t stop at fucking three or four? I had to have eight?”

But his crisis in confidence is manifested in subtler, more impressive ways. To differentiate Rick from the characters Rick portrays on screen, most notably TV cowboy Jake Cahill on Bounty Law and CalebDeCoteau, the heavy on Lancer, Leo gives Rick a stutter that only materializes when he’s not in character. None of the characters that Rick portrays have a stutter. It’s only Rick.

It would’ve been easy for this choice to backfire. But Leo plays it subtly enough that isn’t a distraction or an impediment while still being noticeable enough for the audience to pick up on it immediately. He also gets it right. As pointed out by someone with expertise in this arena, Leo “blocks on certain words and switches words mid-sentence to something that’s easier for him to say. This issucha familiar experience for any person who stutters …”

When the movie opens with a flashback to an on-camera interview Rick gives while in his prime as a cowboy on Bounty Law, Rick doesn’t stutter. He comes across as confident and in control. It’s a far cry from the Rick we see mere moments later in a post-Bounty Law world, a world that’s suddenly turned its back on him. It takes us two scenes to understand Rick’s plight. We understand the source of his anxiety. All it takes is Leo giving Rick a stutter.

But Leo isn’t just asked to play a fading alcoholic actor. He’s also asked to play an actor who sucks and an actor who doesn’t suck, all the while maintaining his performance as Rick.

When Leo pretends to suck at acting, man oh man, does he suck. Rick can’t remember his lines while shooting his first scene on Lancer. After he needs a line fed to him mid-scene, he begins to overcompensate for his shitty memory with outrageous facial expressions. It’s truly terrific bad acting. I’m nearly certain it’s the best bad acting Leo’s done throughout his entire career.

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The breakdown in his trailer commences. It might be one of the funniest and most relatable moments in the movie, but it’s not all fun and games in that trailer. It gets quite dark. Rick laments his decision to get drunk the night before. He promises to stop drinking. He takes a swig from his flask. He throws the flask out the door. And then he uses a mirror to tell himself to get his act together for the next scene, otherwise he’ll “blow your fucking brains out tonight. All right? Your brains are gonna be splattered all over your goddamn pool. I mean it, motherfucker. Get your shit together.”

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Then, he goes back out there and proceeds to deliver a believable performance as the heavy. The margin of error — for Leo — is high.

The kind of show we’re watching isn’t one that exists today, so the dialogue inherently rings corny. He’s saying shit like “you come down here for a Boston Social or we gonna talk price?” and “I’d say $50,000 would buy me a whole lot of chicken mole in Mexico.”

It’s supposed to sound stupid to our modern ears, but it can’t sound so stupid that we don’t buy Rick’s performance as Caleb. We have to believe Rick is genuinely good at acting so that when Julia Butters’ character tells him, “That was the best acting I’ve ever seen in my whole life,” we believe her. We don’t just think she’s saying it to be nice to the emotional unstable actor who is one bad day away from hitting rock bottom.

It’s a thin line to walk, but Leo straddles it perfectly.

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And then, he’s right back to being Rick again. Only now, he’s slightly more secure in his acting chops, open to the idea of going to Rome to star in Spaghetti Westerns, and already back to drinking with Cliff again — although he does not at all sound remotely interested in that acid-dipped cigarette.

The film skips ahead six months to August, to the night of the real-life Tate murder. This is the half day of the two-and-a-half days the film shows us. From this point on, it’s mostly Brad’s time to shine. He’s the one who trips on an acid-dipped cigarette. He’s the one who teams up with a dog to take down the Manson murderers in brutal fashion, while tripping on an acid-dipped cigarette that moments earlier had him utterly fascinated with the mechanics of a can opener and curious enough about dog food to take a full-fledged lick.

But this was always, as Tarantino put it, “Rick’s story”, not Cliff’s.

That might seem obvious given that Leo was up for Best Actor and Brad was up for Best Supporting Actor, and that Rick is the actor and Cliff is just the actor’s gopher, but the fact of the matter is that Leo and Brad are more equal co-stars than star and co-star — in real life and in the movie — and Rick and Cliff receive roughly the same amount of screen time in the film. They could’ve conceivably nominated Brad for Best Actor and Leo for Best Supporting Actor. There’s a reason the two actors are introduced simultaneously during the opening credits with their names appearing over the other one. They’re on equal footing.

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But Rick is the emotional center of the movie. He’s also the reason the movie is able to give Sharon Tate the kind of open ending that she deserved. We don’t know what happens after the night/morning of August 8-9, 1969 in Tarantino’s alternative history, but it has to be better than what actually happened 50 years ago. Death is soterriblyfinal, whilelife is full of possibilities.

Without Rick’s drunken intervention, the Manson murderers go to Sharon’s house and kill everyone there, and history stays the same. It’s only because of Rick that the Manson murderers decide to target his house rather than Sharon’s. While Cliff walks Brandy and smokes his acid-dipped cigarette, Rick is making margaritas in a very short robe. He’s already blitzed after dinner with Cliff. He hears the Manson murderers’ car idling outside Sharon’s gate. Annoyed at the noisy car and the hippies sitting inside it, he confronts them — carrying the entire pitcher of margaritas with him while still wearing that goddamn robe. He screams at them to leave and to go smoke dope elsewhere.

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His intentions aren’t pure. He doesn’t think he’s saving Sharon or anyone else in that house from death. He screams at the Manson murderers and calls them mean things (“you littleginger-hairfucker”) because he’s disgusted at the noise their car is making — never mind the fact that he’s blending margaritas at midnight while his wife tries to sleep down the hall. He just wants to drink in peace. He’s a drunk. And he’s drunk.

But it works. The Manson murderers flee, regroup, and after realizing who the man that just yelled at them is, decide to kill Rick instead of Sharon, because they want to kill an actor who taught them how to kill (it’s less of a half-baked idea and more of a baked-as-fuck idea). From there, as Rick drinks an XXXL margarita and jams the fuck out on a pool floatie, oblivious to the invasion of his home, Cliff and Brandy go to work on the Manson murderers.

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Rick is oblivious to the threat until one of the Manson murderers — the only one still alive — stumbles through the glass and into the pool, firing a gun into the night sky. That’s when Tarantino gives Leo the best moment in the movie, a moment that is earned after Tarantino sprinkled breadcrumbs throughout the previous two hours.

During Rick’s meeting with the agent on Day 1 of the movie, The 14 Fists of McCluskey is discussed — specifically, how Rick actually operated the flamethrower to torch a bunch of Nazi’s in the film.

“That’s one shit-fuck crazy weapon you do not wanna be on the wrong side of. Boy, oh, boy,” Rick says. “I practiced with that dragon three hours a day for two weeks. Not just because I wanted to look good in the picture, but because I was shit-scared of the damn thing, to be honest.”

On Day 2, while Rick is filming Lancer, Cliff heads back to Rick’s house to fix his TV antenna. First, he stops in the shed by the pool to grab tools. It’s easy to miss — I did on my first viewing — but against the wall of the shed rests the same flamethrower from The 14 Fists of McCluskey.

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So, when that Manson girl stumbles into the pool, shooting a gun into the night sky, Rick abandons floatie and heads straight for the shed. He returns with the flamethrower. The first time I saw the movie, the stranger sitting next to me couldn’t help but yell “the flamethrower!” before Rick even fetched it. I normally hate people who talk during movies — and people, in general — but I was okay with the disturbance this time. It’s a movie moment I won’t ever forget.

It’s my favorite moment in a movie since the ending of Rogue One.

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“My buddy and his dog killed two of them, and then, uh, well, shit — I torched the last one. … I burnt her ass to a crisp,” Rick tells Jay Sebring, a “friend” of Sharon’s (it’s complicated), who wanders down the gated driveway to ask Rick what the hell just happened after police leave the scene. He’s standing on the other side of the gate. Sharon buzzes down for an update. She talks to Rick, who is flattered to learn that Sharon knows who he is. She invites him up for a drink. The gates open. They’re no longer sealed to him. He enters the Polanski residence. Sharon ushers him inside. The movie ends.

Rick accidentally saved Sharon. In the process, he might’ve resurrected his own career.

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The first time I watched the film, I was uncomfortable. I couldn’t settle into the movie at any point really because I knew the movie was about the Sharon Tate murder and I for two-plus hours, I was dreading the final act. I didn’t want to watch Sharon get brutally murdered. It felt wrong. And then the final act happened the way it did and I realized I was an idiot. Tarantino never had any intention of murdering Sharon. And he made his intentions clear right there in the title: Once Upon a Time. It’s a fairytale. It was from start to finish.

We don’t know what happens once the film fades to black a couple hours later. All we do know is that Rick makes his way through the gates and into the promised land after one heck of an impromptu pool party. Maybe he develops a genuine friendship with Sharon. Maybe a starring role in a Polanksi movie comes next. Maybe he gets nothing more than a sympathy drink with Sharon before heading back home to Francesca and Brandy, bringing bagels to Cliff in the hospital in the morning as requested, and resuming his trajectory as a Hollywood has-been.

I know what I’ll choose to believe what happens next. Rick already predicted it.

“Here I am flat on my ass, and who I got living next door to me? The director of Rosemary’s fucking Baby, that’s who,” Rick tells Cliff after his come-to-jesus meeting with the agent at the end of Day 1. He’s just watched Sharon and Polanski pull into their driveway. It’s the first time he’s caught a glimpse of them since they moved in next door. “Polanski is the hottest director in town right now — probably the world. He’s my next-door-fucking neighbor. Shit. I mean, who knows what could happen?

“Shit,” Rick says, “I could — I could be one pool party away from starring in a new Polanski movie.”

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Once Upon a Time in Hollywood isn’t just Leonardo DiCaprio’s masterpiece. It isn’t just Tarantino’s attempt to rewrite history and save Sharon Tate. It isn’t just Brad Pitt’s first acting Oscar win. It isn’t just Leonardo DiCaprio’s worst nightmare. It’s also Rick Dalton’s fairytale. And in a fairytale, Rick Dalton lives happily every after.

I mean, who knows what could happen? Shit, he might just become Leonardo DiCaprio.

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