How Brad Pitt, Hollywood Darling, Ran a Perfect Oscar Campaign

By Kayleigh Donaldson | Celebrity | February 7, 2020 |

By Kayleigh Donaldson | Celebrity | February 7, 2020 |

This year, the Academy Awards feels defined by familiar narratives and well-known faces. While we’re all not-so-secretly hoping that the big winners of the night will be the Hollywood unknowns of Parasite, the safest predictions of the season come from major stars with the glitzy stories to match. Renee Zellweger is the comeback queen emerging back into the spotlight through her stellar embodiment of a cinematic legend. Laura Dern is industry royalty experiencing a second boom in popularity through film, television, and growing fandom enthusiasm. Joaquin Phoenix is an acting veteran with over 35 years of work to his name and a reputation as one of his generation’s greatest talents, surrounding him with the aura of this season being ‘his time.’ And then there’s Brad Pitt.

Pitt didn’t seem like the expected Oscar front-runner for his performance in Once Upon a Time in Hollywood when the film premiered at the Cannes Film Festival in May of last year. For one, it’s certainly not a supporting performance, as he and Leonardo DiCaprio dominate the narrative over those 160 or so minutes. It didn’t seem flashy enough for the Academy’s taste, nor did the performance delve into the showboating or clip-ready moments that Pitt’s previous nominated work did. Yet once the Golden Globes kicked off and Pitt took home his award — it was his second win for acting after 1996’s 12 Monkeys and his 11th nomination overall — it seemed that everyone was happy to put him on the fast-track to the Oscar.

In hindsight, it shouldn’t be all that shocking. First of all, it’s a damn good performance, arguably one of the actor’s best. It’s the sort of role that only a true Grade-A leading man can pull off in terms of charisma, sex appeal, and the sheer amount of metatextual layers going on underneath the surface. In a year where most of the sure-fire acting winners are being celebrated for work that is nowhere near their best, Pitt is a refreshing exception. It doesn’t hurt that he’s working in a Tarantino film all about the majesty of Hollywood and the end of an era for golden age macho dudes and all that they embody. Still, in a year of such tough competition, which includes long-time legends like Al Pacino, Tom Hanks, and Anthony Hopkins, for many months this category was up in the air and Pitt felt like the kind of guy you would nominate but not necessarily give the win to, much in the same way DiCaprio has been this season for the same film. Pitt, however, had something that none of his competitors and very few of his industry contemporaries possess: Pure unmitigated star power.

Make no mistake: Brad Pitt is wildly famous. He’s the kind of famous that we don’t really have anymore and he’s been one of the biggest stars on the planet for close to 30 years. While the very meaning of Brad Pitt has changed over the decades, his immense appeal has never diluted, even as he’s faced public scandals, shady rumors, and more than a few movie flops. Now, at the age of 56, it feels like his upcoming Oscar win is the cherry on top of the cake, the welcome but not demanded confirmation that he is One Of The Greats. More importantly than that, at least in the eyes of his peers, he’s just that well-loved!

It doesn’t hurt to be beloved when you’re part of the year-end popularity contest that is awards season, and it remains extremely easy to like Pitt. As demonstrated by his series of excellent acceptances speeches, he knows how to work a room and sell himself as a viable candidate without resorting to vague platitudes or Oscar-baity clichés. Self-deprecation is the name of the game here. All of his speeches have relied on making himself the butt of the joke, most frequently through his divorce from Angelina Jolie. Audiences and his colleagues have eaten it up, even when he isn’t there to give the speech. They love this Brad who is handsome and talented and rich but willing to make himself the clown even as he picks up a new shiny gold statue. Interestingly, he’s managed to continue this spiel without making people turn against him for using his ex-wife as a joke. It could have been a very risky strategy, especially since it’s public knowledge just how messy that split has been in large part thanks to his drinking. The details of why the FBI was called onto a plane the family was using also remain seriously suspicious. Pitt has played a smart PR game since the split and people are always willing to give points to those who use humor as a way to break the ice. Plus I’m sure it doesn’t hurt that he’s the guy in this situation. When he first got together with Jolie after splitting with Jennifer Aniston, the tabloids were too focused on the catfight to pay attention to the man in the middle.

Of course, it’s not enough just to be likable or put in a great performance. The Academy wants a full story with a beginning, a middle, and an end, and over the course of his career, Brad Pitt has spun one hell of a yarn. He evolved into the consummate character actor after establishing himself as the ideal beefcake who appealed to men and women alike, from Thelma and Louise to Fight Club. Pittmania was near-inescapable for a serious chunk of the 1990s, not that you could blame anyone. He was just that good looking. He also wasn’t taken as seriously as an actor for a while, even as he built up an impressively eclectic filmography that included Interview With the Vampire, Fight Club, Seven, and 12 Monkeys, the movie he landed his first Oscar nomination with. For every conventional hottie movie or blockbuster title, there was an offbeat drama or auteur-driven title. Pitt’s never gotten enough credit for how genuinely weird his career was for a guy who was primarily defined as a sex symbol for decades, especially when you compare him to contemporaries like Tom Cruise, who took a far more conventional A-Lister route.

The true ace up Pitt’s sleeve, and one of the biggest reasons he’s garnered so much goodwill, is Plan B Entertainment. Originally founded with Aniston, Pitt molded the company into one of the most prestigious and savviest of production houses in the industry. They have eight Best Picture nominees/winners to their name and films from directors such as Ava DuVernay, Steve McQueen, Bong Joon-ho, Barry Jenkins, Terrence Malick, and Miranda July. Pitt has thrown his support behind some exceptional film-makers but it’s worth noting how much he focuses on the work of black directors. He knows how many doors his name opens in the business and how that can benefit the most marginalized voices, so he’s doing the work. Being a beloved actor is one thing, but being a true Hollywood power player is something altogether more worthy in an industry that craves it.

Pitt’s victory lap will come to an end on Sunday and I’m sure his win will inspire one hell of a standing ovation. He’s come a long way for this and has a lot more to offer as he heads into his 60s. It’s rare that any celebrity can remain as popular and respected as he has for so many decades with nary a scratch or stain to his name. The divorce from Jolie and the stories that swirled in its aftermath easily could have put a serious tarnish on his career, and yet it barely touched him. Few A-Listers can get away with that, for better or worse.