5. Seven (1995) – David Fincher
Many of Brad Pitt’s earlier films feature characters who undergo little emotional development; rather, he tended to play a static type which suited the tone of the movie. Seven was a bit of exception, however; though his protagonist never reaches full maturity, we at least see an evolving character. The rash young detective Brad plays works best when pitted and contrasted against Morgan Freeman’s steady presence.
Seven is an undeniably dark journey into an always smoldering underworld that only reveals itself to the general public as an occasional flare in the news headlines. But to a pair of homicide detectives (one ready to retire, and another just starting his career), these monstrosities are banalities. Despite the seemingly familiar plot points, this is a tale designed to upend the expectations of everyone, and the narrative shifts into overdrive suddenly and unexpectedly. The cynical veteran is forced to admit that he has not, in fact, seen it all, and the cocky rookie receives a first-hand lesson on the nature of evil from a true expert, with whom he discovers more in common than he ever dared imagine.
4. The Assassination of Jesse James by the Coward Robert Ford (2007) – Andrew Dominik
This modern classic put Pitt’s quiet, brooding aura to its best possible use. Playing an outlaw on the run, he settles into the role of the ostracized loner as comfortably as into a well-worn cowboy hat. Suspicious of the world and distrustful of those closest to him, his character is simultaneously on edge and withdrawn. As Jesse James, Brad Pitt turns in one of his very best efforts here.
The outlaw Jesse James is as legendary as they come. With a larger-than-life persona which only grew after his death, James has been the subject of countless stories and myths. It’s no spoiler, in this case, to point out that this film deals with his assassination by someone who worked his way into James’s inner circle. Watching the personal dynamics of the betrayal is intriguing to watch, and this is an indisputably beautiful modern Western.
3. The Tree of Life (2011) – Terrence Malick
The unconventional narrative structure of this film presents us with alternating perspectives of life as macrocosm and microcosm. We see the travails and tragedies of a small Texas family through the eyes of one of the sons reflecting on his youth. Brad Pitt performs perfectly as the strict father of the family – at times tormented and toxic, occasionally resigned and kind. He brings a wonderful authenticity and depth to the role, doubtless inspired by his own strict upbringing. His unexpected replacement of the late Heath Ledger in the film turned out to be a stroke of genius, and it’s a performance to treasure.
We’re told, as the mother in the film tells her children, that there are two paths in life – the path of nature, represented by the authoritarian father, and the path of grace, shown by the submissive and loving mother. Interspersed with the drama of family life and adolescence are sublime sequences showing the power of nature, the vastness of the universe, and the complexity of evolution which immediately throw into perspective the seemingly minor circumstances of any individual. The Tree of Life knows that it’s tackling a subject of immense depth, but this gorgeous film succeeds as well as is humanly possible.
2. Ad Astra (2019) – James Gray
This is the most recent film on this list, and it certainly earns its place as the most mature acting work by Brad Pitt to date. Here we witness a protagonist approaching full emotional maturity, presented through a performance of amazing dedication. He truly inhabits the character, and thoroughly pulls the audience into both the film and the experiences of its inhabitants.
In Ad Astra, Pitt plays an astronaut whose father (also an astronaut) disappeared in space many years ago. But when scientists start receiving strange signals from the area where he disappeared, they recruit the son to travel to Mars and try to re-establish contact with his father. Though ostensibly about one man’s journey into the outer reaches of our solar system, Ad Astra is also about his journey into the depths of his own spirit. It’s a beautiful and meaningful film.
1. Fight Club (1999) – David Fincher
Brad Pitt was hardly a struggling, unknown actor in 1999, but this year guaranteed that he would enter the new millennium cemented as a box office star. In a role that still defines him for many movie lovers, Fight Club funneled his talents into the mold of an unforgettable character of archetypal machismo. Sure, the role only highlighted one aspect of his talents, but it brought out the very best in its star in the process.
Chuck Palahniuk’s novel was the basis for this culturally iconic film which confirmed the star status of its lead actors – Edward Norton and Brad Pitt. Norton plays a bored white-collar office worker who is drawn into an underground fight culture by Tyler, played by Pitt. Tyler is a cocky soap salesman who represents a counter-culture which his new friend can’t resist exploring. Their unlikely friendship is the basis for an astute study of the modern male ego learning to survive in an existentially fragile environment, and Fight Club remains an important film. All things considered, it’s difficult to place any other movie as Brad Pitt’s very best so far.