Among Brad Pitt's early roles, one of the most recognizable is as J.D. in Thelma & Louise, Ridley Scott’s classic road movie with Susan Sarandon and Geena Davis. It’s one of the roles where Pitt exudes his villainous charm, playing a thief who seduces one of the women to escape with her savings.

Pitt's big career rise came during the 90s, with one of his most iconic roles coming mid-decade as rookie agent David Mills in Se7en, directed by David Fincher, also a star director on the rise. Here, Brad Pitt is the volatile, impulsive counterpart to Morgan Freeman's veteran and wise detective – a dangerous combination against the serial killer’s manipulations they are trying to apprehend.

Another collaboration with Fincher resulted in what might be the most iconic character of Pitt’s early career (and also sparked his heartthrob reputation): Tyler Durden in Fight Club. The extroverted, charismatic, cynical – and (spoiler) alternate personality – of the protagonist-narrator (Edward Norton) is the foundation of the narrative about the alienating disassociation from the consumerist world the film critiques.

Brad Pitt’s heartthrob powers peaked as the warrior Achilles in Troy, a loose, spectacular but conservative adaptation of Homer’s The Iliad. The Achilles myth isn’t faithfully adapted here, but as the leader of the Achaean army against the Trojans, Pitt sports an impressive physique that solidified him as a favorite icon of the 2000s, even though the role didn’t require much of his dramatic talents.

Later in his career – and older – Brad Pitt began to seek more interesting and demanding roles that showcased his versatility. One of the most underrated was in the equally underrated dark comedy by the Coen brothers (The Big Lebowski), where he plays a goofy gym trainer dragged into his colleague’s obsessive scheme (brilliantly played by Frances McDormand), with hilarious – and tragic – consequences.