I don't have any particular nominees, in part because so many wonderful songs reflect that point in life.
I think there's a particular truth, though, that much of Jim's work is reflecting on those 'lost opportunities' – or, perhaps more accurately, he often reflects back on the loss of such possibility and attempts to recapture it, in part through often wonderfully overwrought effort and a particular wry exuberance.
The dangerous thing about this process is that it's self-fulfilling. The attempt to recapture or effectively lament the lost possibility of the past tends to lock one in that loop, and is precisely what tends to compromise renewed possibility.
Folk of high school age are rarely reflecting on lost possibility, that's a business for post-high school, though it often begins shortly after high school.
'High School Never Ends' by Bowling For Soup comes to mind.
Al
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