Despite his leading man looks and movie star charisma, actor Brad Pitt spent most of his career trying to avoid box office sure things in favor of riskier, lower-profile work. After achieving heartthrob status with revealing performances showing off his six-pack abs in "Thelma & Louise" (1991) and "Legends of the Fall" (1994), Pitt actively subverted his hunky image by taking on ugly and often crazed characters, most notably in "12 Monkeys" (1995), "Fight Club" (1999) and "Snatch" (2001). While en route to becoming one of the top box office draws of his generation, Pitt generated a substantial amount of tabloid press, particularly for his headline-grabbing romances, which provided ample fodder for supermarket stands across the country. His high-profile marriage to "girl next door" Jennifer Aniston - once considered the Hollywood ideal - publicly imploded after he separated from his wife and began dating archetypal bad girl Angelina Jolie. The result, however, was a new image of Pitt as multiracial father and globetrotting activist, thanks to Jolie's adoption of impoverished orphans from around the world. (After months of rumors about the state of their marriage, Jolie filed for divorce in September 2016.) This transformation was underscored by strong and mature performances in the meditative "Babel" (2006) and "The Curious Case of Benjamin Button" (2008), as well as more escapist fare like the "Ocean's Eleven" franchise. As he matured into a graceful middle age, Pitt's range only widened, moving effortlessly from Quentin Tarantino's World War II fantasy "Inglourious Basterds" (2009) and the zombie thriller "World War Z" (2013) to smaller fare like the existential gangster drama "Killing Them Softly" (2012). Roles in Steve McQueen's Oscar winner "12 Years a Slave" (2013) and Adam McKay's "The Big Short" (2015), both of which he also produced through his Plan B Entertainment shingle, proved that his eye for picking challenging but popular material was unsurpassed. The public's fascination with the beloved actor both on screen and off proved that beneath the pretty boy exterior, Pitt only improved with age.