I love both photos... I know why #2 would be your favorite - I'm quite familiar with that look, too!
The first photo has the nicer background and the natural light will help the photo print nicely on the calendar... that's the only reason I would pick #1 over #2. But if you think #2 reflects his personality and everything you know of him better than #1, I'd say use #2.
I've never said "#1" and "#2" so many times without giggling before in my life.