Seth Poppel/Yearbook Library
Adam Levine wasn't quite cover-boy material back in high school, but he was pretty darn cute. (Sorry, this is not an ugly duckling grows into beautiful, tattooed swan tale.)
Now, though, he is People's 2013 Sexiest Man Alive, engaged to model Behati Prinsloo, coaching The Voice and, yes, pretty much winning at life. He even met a couple of his Maroon 5 bandmates during his days at L.A.'s Brentwood High, and his teenage sweetheart Jane Herman (who would eventually become a Vogue editor) is actually the Jane from Songs About Jane, the band's 2002 debut album.