Bradley Cooper - 2001
Long before he was named People's Sexiest Man Alive in 2011, Bradley Cooper was a heart breaker. "When I was a kid, my mom took me shopping a lot. I hung out at the makeup counter asking pretty women for kisses," Cooper once told InStyle. The days of stealing kisses at the makeup counter may be far behind him, but he still makes women stop in their tracks with his blue eyes, gorgeous smile and funny-guy personality.
In 2001, Cooper pulled off an unkempt look nicely, with shaggy blonde locks and a scruffy face.