Thanks for all the thoughts everyone. Getting back to a few people:
1. He was in the military. First the Navy then the National Guard for a number of years.
2. Good idea about a class, I would like to do that with my dad and brothers, but it isnt really an option as they both live 500-750 miles away from my folks. Same goes for a gun show, hard to get all the brothers together.
3. I talked with my brothers, and while I like the 1911 idea, they are leaning more towards a rifle, so rifle it is.
4. I think we will print out some options for him, and have him open a gift containing the ideas that we had. Then, he can use those as a guideline to pick out something that he likes. Dont want to just ask him though, becuase while I certainly understand that firearms are personal, this is a gift and we want to have some input, not just front the $. That certainly doesnt show alot of thought.
5. We have always been pretty informal (not unsafe, just informal) in how we shot at the range. Plinking at stuff with .22 and handguns and handthrowing clay pidgeons. I understand that if we get him a nice rifle, a more formal range with longer distances would fit the bill better
6. I like the custom engraving idea, might look into something like that. Although, with dads taste, it would have to be pretty understated.
All that said, there are some good ideas here! I will put in lots more thought with my bros, but right now I am thinking of Cooper, Weatherby Sporter, Browning BAR Safari, and Kimber 84m Longmaster Classic.
Looking at the 1911's though, I might have got the bug. Tax return time is right around the corner!