While he may never be able to surpass his 1990s acting efforts, Brad Pitt came pretty close with the one at hand: the 2000s. These are some of the most iconic roles of his career, and the projects themselves resulted in excellent earnings for Pitt. These films actually raised money at the box office, pretty much across the board.
And Pitt was one of the biggest actors working in Hollywood at the time. Of course he still is. But that meant most of these titles were also directed by respective industry juggernauts. And eventually they joined forces with Pitt to make these, his best films of the 2000s.
10 Troy
Based on Homer's epic poem The Iliad, this historical war movie starring Eric Bana as Hector and Brad Pitt as Achilles. While not exactly a critical success - it has a 54% on Rotten Tomatoes - Troy (2004) earned nearly $500 million at the box office, becoming the eighth highest-grossing film of its year.
For the most part, few could have portrayed Achilles in a more impressive way, and the same can be said for the rest of the cast and their respective characters. Eric Bana as Hector, Orlando Bloom as Paris, and Diane Kruger as Helen, just to name a few. The roster of actors and their respective efforts were easily the film's biggest takeaways, especially considering the lackluster script they had to work with.
9 Ocean's Thirteen
The second sequel to Steven Soderbergh's remake of the classic Rat Pack movie, Ocean's Thirteen (2007) features everyone from the first part of this trilogy - guys like George Clooney, Matt Damon, Brad Pitt, Bernie Mac and Don Cheadle. Additionally, there are two additional members of the titular thieving group: Andy Garcia as Terry Benedict and Eddie Izzard as Roman Nagel.
And this third performance far surpassed the quality of its predecessor - Ocean's Twelve (2004), which in fact did not make the list. The original from a few years earlier certainly did, but more on that later. As regards Thirteen: It tends to fall back on the original movie in structure and story conventions, and that works out for the best in the end. This isn't the best movie you'll read about today, but it certainly isn't the worst.
8 Mr. and Mrs. Smith
Without turning around, Mr. and Mrs. Smith (2005) is primarily remembered nearly two decades later for two reasons: its successful run in theaters and its pairing of Brad Pitt and Angelina Jolie. Naturally, the two would marry each other after falling in love on set, a relationship that attracted seemingly endless amounts of media attention for many years that followed.
And in the end, it's their burgeoning but palpable chemistry that propels the movie into eighth spot on this list. It's not the best action movie, and it's not a very compelling comedy either. But with the duo present teaming up with a unique premise - two married hitmen tasked with killing each other - the result is a mostly fun film that will still entertain you today.
7 The curious case of Benjamin Button
Based on the short story of the same name by F. Scott Fitzgerald, Pitt stars here in the titular role as a man who ages in reverse. This was Pitt's third collaboration with director David Fincher Seven (1995) and Fight club (1999). And despite the dynamic duo collaborating once again with a script based on a piece of classic American literature, The curious case of Benjamin Button (2008) polarized critics even after its release.
However, it earned more than $300 million at the worldwide box office and a whopping thirteen nominations at the 81st Academy Awards - by far the most of the ceremony. And while the film drags at times at two and a half hours, it succeeded in so many technical aspects that it finally lands here at number seven.
6 Burn after reading
Directed by Joel and Ethan Coen, Burn after reading (2008) has gone off the radar of the public in terms of longevity. It made a lot of money in theaters, and while critics were a bit mixed about its overall quality, many of the Coen Brothers' movies are often underrated in both regards. However, it remains an entertaining dark comedy about a pair of unusual gym employees (one played by Pitt, the other by Frances McDormand) who come across a manuscript they mistake for valuable government documents.
And the rest of the cast also hit home in classic, quirky Coen fashion, from George Clooney and Tilda Swinton to John Malkovich and Richard Jenkins. And while the plot can be hard to keep up with at times, it's that unpredictability that makes the Coens so great. Audiences never know what to expect - and neither does Brad Pitt's character, for those who have watched the film.
5 The murder of Jesse James by the coward Robert Ford
As half of the titular characters, Brad Pitt appears in this revisionist Western as Jesse James, the leader of the aptly named "James Gang." His performance was somewhat overshadowed by costar Casey Affleck, who appeared as the other half of the two titular characters: Robert Ford.
Based on real events, the histrionic storylines are likely to grip you by themselves. But if not, the stunning camerawork - courtesy of legendary cinematographer Roger Deakins - is bound to inspire you, whether those new desires involve adventure, art or even something more personal. It's an emotional journey The murder of Jesse James by the coward Robert Ford (2007), and even with its aggressively long title and equally long storyline, its quality will prove well worth your time.
4 Jerk
In this movie, directed by Guy Ritchie, Pitt plays a prizefighter named Mickey in his best performance of the decade, bar none. Two of the next three entries also feature Pitt's admirable efforts, but his work in this Jerk (2000) are really career-defining things. While his emphasized Irish accent drew harsh reviews from more linguistically minded critics, his phonetic and physical delivery was nothing short of impressive.
It takes talent to portray such an outlandish character, and Jerk is certainly packed with it - the ensemble cast performs to a degree that doesn't quite reach Pitt's caliber, but guys like Jason Statham and Benicio Del Toro certainly came close. It is arguably Ritchie's best film to date, and while this film ranks Brad Pitt's individual projects in the 2000s, it would undoubtedly come out on top if it focused solely on his performances.
3 Ocean's Eleven
Directed by Steven Soderbergh, Ocean's Eleven(2001) sees Brad Pitt appear alongside Matt Damon and George Clooney - with the latter starring. However, it also features an ensemble cast, with other famous players such as Julia Roberts, Don Cheadle, Bernie Mac, and Casey Affleck all appearing in supporting roles.
This is considered the best heist movie of the twenty-first century, also one of the best remakes, and the featured heist sequence is among the highest rated ever filmed. Brad Pitt also eats a lot, so there's not much to hate in these charming and entertaining antics through a Las Vegas casino. The charismatic characters and well-written dialogues will have you looking forward to a second viewing in no time.
2 Babylon
Directed by Alexandro Gonzales Iñárritu before he really got big, Babylon (2006) really shot the director to stardom when it received a nomination for Best Picture, Best Director and many more at the Academy Awards. It features an ensemble cast working within a multi-story structure - numerous point-of-view characters, individually branching storylines that eventually tie together. All that good stuff.
And audiences will definitely feel a connection with each character operating in their respective storylines. Their personalities seem idiosyncratic from the start, and the portrayals deserve an entry for themselves: Brad Pitt, Cate Blanchett, Koji Yakusho, Rinko Kikuchi, and Adriana Barazza all hit a memorable level. The film as a whole will leave you thinking about its delivery from a technical perspective for many years to come.
1 inglorious bastards
This isn't the best Brad Pitt performance of the decade - that title goes to Jerk. It wasn't the best performance in the movie itself, either. Of course, that has to be Christoph Waltz as SS Colonel Hans Landa. But honestly, this isn't even the best performance of Pitt's two collaborations with director Quentin Tarantino, as his role in Once upon a time... in Hollywood (2019) earned him the Academy Award for Best Supporting Actor.
Still, it remains the best movie Brad Pitt starred in in the 2000s, and that's hardly a contest. He stars as Lieutenant Aldo Raine, who leads the titular group of American soldiers as they hunt down Nazis and execute an assassination plot against Hitler and his top cohorts. There are unlimited amounts of technical movie making tactics to praise inglorious bastards(2009), but in the end the number one spot is good enough.
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