Brad Pitt and Angelina Jolie are headed to a divorce, which means two things for us mourning fans: One, love is dead, and two, Brad Pitt is on the market. The Hollywood heartthrob has made moviegoers swoon since his breakout role in the 1991 classic Thelma & Louise, even topping People’s “Sexiest Man Alive” list twice—in 1995 and 2000—throughout his career.
It’s easy to see why: He’s handsome, charming, and just one look at those baby blues gets our hearts beating faster. Whether he’s blonde, brunette, or just plain shaggy, Pitt manages to always look good on a carpet.
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Now, the Mr. & Mrs. Smith star is single for the first time in decades—He split with Jennifer Aniston in 2005 after meeting Jolie on the set of their 2004 film. With this sexy star back on the market, we’re taking a look back at his incredible transformation and imagining what we would look like on a red carpet next to this dapper star (too soon?).
Brush up on his changing looks through the years in our gallery.