Then: A dreamy-eyed, 25-year-old actor from Missouri named Brad Pitt had already turned up on TV shows like "21 Jump Street" and "Dallas," but he was still three years away from landing his attention-grabbing role as the shirtless cowboy who literally charms the pants off Geena Davis in the 1991 movie "Thelma and Louise." Pitt was eight years away from his first of four (so far) Oscar nominations, including three for acting and a fourth as a producer of 2012 Best Picture nominee "Moneyball."
Now: Pitt, 49, still makes us swoon — even with the long hair he's been sporting as of late. He's a well-respected philanthropist, as well as a wine maker, furniture designer, and fiancé of fellow A-lister Angelina Jolie, who once had a thing for goofy hats herself, not to mention co-parent of their six kids. Of course, he also garners raves for his acting chops, and his latest movie, the big-budget zombie thriller "World War Z," opening June 21, is already receiving mostly positive reviews.
Who do you think looks more totally awesome in their hat — Brad or Angelina?
More Celebrity Features on Yahoo!: