From his breakthrough role in Thelma and Louise to his most recent, critically acclaimed performance in Once Upon A Time… In Hollywood, Brad Pitt has been embodying iconic characters for almost 30 years. Not only is Brad Pitt an incredible actor, but he is a good judge of characters and stories; hence why so many of his characters leave an impact on the viewers. It’s clear that the actor chooses his projects wisely, something which has allowed him to renew himself with both leading and secondary roles in all kinds of genres: comedy, thriller, drama, romance, and even sci-fi.

Brad Pitt’s most memorable characters are thus all individually different: dumb or smart, good or evil. Here we rank Brad Pitt’s 10 most iconic characters from most heroic to least heroic.

Se7en

We all remember vividly David Mills’s cries of “what’s in the box?” during the climactic scene of Se7en - but before he was turned into wrath by John Doe, Detective Mills was a good man who only wished to help protect the city against serial killers. The character is relatable despite his unusual journey. Whereas Morgan Freeman’s character seems more used to the horrors of the world, Detective Miller is not. Young and a little naive, he is full of ambition and compassion, making his downfall all the more heartbreaking. The movie is a tragic look at how even the best of men can be turned to the dark side, out of anger and sorrow.

Fury

Fury may seem like just another war movie about the Second World War, but it takes a beautiful approach to the subject by focusing on a group of American tankers as they are faced with an impossible mission of holding a crossroad against an SS stallion of 300 German soldiers. Brad Pitt plays Wardaddy; the leader of the tank named Fury.

He appears insensitive and is harsh on the soft-hearted, but is honorable and fights for his country until his dying breath. Even when the German army is on its way, Wardaddy decides to stay and complete his mission, even though he knows it will kill him. Although he urges the other men to run away and save their own lives, they decide to fight alongside him. It’s suicide, but Wardaddy’s last words end up saving the youngest soldier.

Troy

Troy took over audiences’ hearts in 2004 for its epic interpretation of Greek mythology and its wonderful casting of Brad Pitt as the famous Achilles. The movie depicts the war between Troy and Greece that led to the devious invention of the Trojan Horse.

Achilles is known in the movie as one of the greatest Greek warriors. Although his decision to keep a female prisoner may seem questionable, he feeds her, gives her water, and does not mistreat her. Eventually, the two fall in love and he does everything to save both her while fighting for his nation - even though she is supposed to be the enemy. Heroically, he dies taking an arrow for Greece.

Once Upon A Time… In Hollywood

Despite being inspired by the real-life story of Sharon Tate, Once Upon A Time… In Hollywood introduces us to the fictional Cliff Booth, an honorable war veteran and stuntman who looks out for his friends. The only thing that keeps Cliff Booth from being Brad Pitt’s most heroic character is the rumor that he has killed his wife. Although his boss, Rick Dalton, doesn’t believe the rumor, a brief flashback shows Cliff at sea, with his wife yelling and putting him down, a scene which seems to imply that Cliff could have easily lashed out and killed her. Nonetheless, Cliff does a fine job of defending his boss, his boss’ wife, and their neighbors. There is nothing more satisfying in the movie than watching Cliff bash the Manson murderers’ brains out when they break into Rick’s house.

Inglourious Basterds

After True Romance, Brad Pitt finally joined a movie written and directed by Quentin Tarantino as Lieutenant Aldo Raine. Although Inglourious Basterds has several protagonists, Aldo stood out for his over-the-top Southern American accent and his passion for killing - more accurately scalping - Nazis during the Second World War.

He is extremely violent in his methods, but it is undeniable that the way in which the character fights to defend and avenge the Jews is heroic. He believes so strongly in the unforgivable wrongs of the Nazis that he cannot even be bribed or commanded to let one Nazi live for having switched sides. He believes that every last one of them needs to be punished for their crimes against humanity, which he does himself.

Mr. & Mrs. Smith

Although Mr. & Mrs. Smith is a movie that is rarely talked about when discussing Brad Pitt’s best performances, his character is iconic. The premise of the movie is fascinating: a married couple suddenly discovers that they are both spies and each has been hiding it the entire time. In this famous couple, Mr. Smith appears to be the more sensitive and compassionate one. Whereas Angelina Jolie’s Jane Smith hits John with her car and almost kills him several times after discovering that he is the enemy spy, John instead wants to talk things through and admits that he could never kill Jane. Together, the unusual duo end up heroically taking down the criminal organization targeting them.

The Curious Case Of Benjamin Button

Unlike the other David Fincher films Brad Pitt appears in, The Curious Case Of Benjamin Button is a slow romantic movie with little to no action. As a mere man trying to live his life with an abnormal condition that makes him age backwards, Benjamin Button is rather neutral when it comes to being heroic or villainous.

He is a good man, that is for certain, and he just happens to live a rather strange life. His life is turned around when he meets Daisy, played by Cate Blanchett and falls in love. However, the two cannot stay together forever, and Benjamin respectfully honors Daisy’s wish to leave his life as his condition cannot allow him to be a good father. Clearly, he is selfless and will do anything for the people he loves.

Snatch

Snatch is considered one of Brad Pitt’s best roles, solely for his incredible and incomprehensible Gypsy accent. Discovered by a boxing promoter, Mickey O’Neil, is a boxing champion who keeps disobeying his orders to go down on the fourth round during his boxing matches. For this, he pays a price - his mother is killed.

Having disobeyed in a match once again, Mickey is about to be killed, but it turns out that he had been planning revenge for his mother all along, and it is the gangsters that try to go after gun that end up being shot by Mickey’s Gypsy friends. The character isn’t really heroic so much as he is someone who the audience roots for: He may seem dumb but he ends up outsmarting everyone.

Ocean’s Eleven

Despite the all-female remake Ocean’s Eight, Ocean’s Eleven remains perhaps the most iconic Hollywood heist movie. Although it is George Clooney’s character that gives the film its title, Brad Pitt’s Rusty Ryan is equally important, and the two characters work together to assemble the perfect team of criminals to pull off an ambitious robbery: three casinos in Las Vegas.

As reasonable and charming as Rusty is, and as much as we want this group of thieves to get away with the robbery, they remain criminals. The only reason we can accept that he is both a good person despite his outrageous scams is that he steals from incredibly wealthy and corrupt people like Terry Benedict.

Fight Club

Unlike the majority of Hollywood’s biggest stars, Brad Pitt’s most famous role is not heroic at all. We all know the first rule of Fight Club thanks to Tyler Durden, the creator of this violent and lawless community. In this satirical cult movie, Tyler tortures the narrator endlessly, he threatens and terrorizes average citizens, and shoves his philosophical beliefs down everyone’s throats.

Tyler is complex, principled, unpredictable, and dangerous all at once; characteristics which are only intensified as we find out that he and the narrator are one and the same.