Despite his leading man looks and movie star charisma, actor Brad Pitt spent most of his career trying to avoid bloated box office roles in favor of riskier, lower profile work. After achieving heartthrob status with revealing performances showing off his six-pack abs in “Thelma and 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 proverbial 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. It was this transformation that 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. 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.