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I would like to put together an "end of an era" set, but honestly don't know if I could make it through so much nostalgia and loss in one go.

The end of an era need not be a downer. Are there no songs of people who have survived bad times? Doesn't 'From Hull and Halifax and Hell' end with escape from the three H's? There must be songs about people who have escaped or been released from slavery.

Also Amazing Grace and Spencer the rover, (Imagine those two getting together!) are songs of redemption. Would those fit? Any others?