Sounds a bit like Oldest surfer on the beach with a few Why worry licks. Nice!
That's what I understand, too. Some ageing (rock-)star perhaps?
He's turning around to find that there are young stars (some Cinderella in this case) who'll do anything to become famous ("fresh out of fame school class", ready to sell even their wedding photo), and they're way more popular that him now, because he's gone out of fashion (=people don't want to pay money for him anymore). He can feel the cold wind of reality blowing (he is no longer "the best in show") and realises he should've stopped long ago (he didn't know when to take his bow, i.e. say goodbye to showbusiness, unlike the summer, which is ending).
