I was going to try and fill the Barely Legal category, but honestly, I feel like a giant perv doing research for that one, so I am gonna leave it for last.
.... So, Team "Thank God, I'm a woman" will select in the fifth round, in the 40+ category, Jeffrey Dean Morgan.
Morgan, born in 1966 putting him just over 40, is most well known for his breakout role in Grey's Anatomy as Izzie's gravebound boytoy in season one (possibly season two). He was most recently in Watchmen as The Comedian. But I picked him because of his role in PS I Love You. He had an Irish Brogue, granted it's fake, but it was still hot and you get to see his gorgeous behind. It was just great. I just think he's charming and rugged and totally swoonworthy.
Oh, and he's one more reason for bigtmac to start watching Supernatural. He played Daddy Wincester to my other picks, Jensen and Jared. The whole darn family is hot.
For any interested parties, his behind is on full display in PS I love you, if you are so inclined to see it, watch that movie or google it. It's out there on the interwebz!