How about "Boys Town"? One of the things I look for in the older B&W movies is how the characters, dialogue, etc. reflect the times. I think we are all pretty familiar with how fashions have changed since the 30s & 40s, but Mickey Rooney's antics do reflect what was cool back then at least for a teenager. There also seems to be a certain naivete that is refreshing when you compare it with the muck and mire in which young peole are immersed these days.