Lyric discussion by idunnowhat 

This song is about passing your prime without accomplishing anything.

The first verse is really about the singer hoping to rediscover old avenues of fortune and inspiration from his younger days, when he was in his prime and all avenues seemed open to him.

The chorus rips on the people who should have been famous for being so artistic and with it and hip all that. The singer self-identifies as one of these "gentlemen losers", with all the posture and none of the necessary substance of action. So he asks to be taken to Harlem or wherever the hip place is now so he can attempt his great reconnection.

Last verse is talking about how all the stuff that was going on when it was cool to be doing what the singer is still doing - i.e. that whole world - is gone. The people, the sense of fortune, etc. It wasn't just a matter of the singer choosing to take part in the world, it was about the juxtaposition of the opportunities with the willingness to take them.

The coup de gras, the killer line of it all, is: "The time of our time has come and gone/I fear we been waiting too long." Like, literally, the years of the singer's invincibility and inspiration are behind him, and all those doors are closed to him now, and he squandered it because he never thought those doors would close.

@idunnowhat I know this may sound a bit obtuse, but the song is about a car - nothing really existential, just a car cruising through NYC.

@idunnowhat New here but, after reading your interpretation of Midnight Cruiser, I thought how ironic that, as good as your take sounds, this is actually SD’s first album and they had so many excellent ones. But maybe Fagen is just an excellent songwriter that it’s his character’s stories.

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