5. Seven (1995)
Brad Pitt’s portrayal of the hungry, ambitious and relatively inexperienced New York detective Mills who – along with new colleague and veteran Somerset (a brilliant Morgan Freeman – finds himself in the middle of a dark spiral of several brutal ritual murders is memorable and brilliant. Pitt plays Mills with a youthful curiosity and a touch of naïveté, while also injecting intelligence, conviction and an almost fanatical desire to catch the killer John Doe into his performance.
4. The curious case of Benjamin Button (2008)
Portraying a character who, in a kind of strange mix between romantic drama and imaginative fairy tale, ages backwards and thus understands little about the world, other people or his own existence – is certainly no easy task. Brad Pitt navigates Benjamin Button in the best possible way, bringing charm, charisma, curiosity, depth and life to his character in a way that should be applauded.
3. The assassination of Jesse James by the coward Robert Ford (2007)
There is a mystery and an elusiveness in Pitt’s portrayal of gunslinger Jesse James that gives this film depth. He has never been more unpredictable than in this interpretation, which the film demanded, and a glimpse of his tormented soul is revealed in a few small moments during the film, which is purely due to Pitt’s brilliant acting.
2. Once upon a time in Hollywood (2019)
Pitt’s performance in Tarantino’s enchanting love letter to 1950s Hollywood is the film’s best, and his character Cliff Booth is undoubtedly the highlight of this film. Booth, thanks to Pitt, is both mysterious and simple. He is both mysterious and cunning, honest and loyal in a way that makes him incredibly charismatic.
1. Moneyball (2011)
Pitt’s acting in the eternally underrated baseball film based on the real Billy Beane (GM of the MLB’s Oakland A ‘s) is certainly his finest hour, although both the film and his interpretation of the role too often fly under the radar. Pitt perfectly captures Beane’s attitude, his bravado and charisma, and captivates with great presence and a charming intensity in the pursuit of victory. It is often easier to celebrate characterizations when the characters themselves are super bad, unhinged or obscure rather than a real, genuine human being as in the case of Moneyball, but I have no doubt that Moneyball is Pitt’s finest hour as an actor.