You can write dissertations about Leonard Cohen's poetry, so I'll basically leave that to others. I'll restrict myself to pointing out the eerieness about a song like this, recalling literary references across the board, from Franz Kafka to Philip K. Dick, by way of George Orwell. Doom is approaching, and Leonard is watching from the front row. "They sentenced me to twenty years of boredom", indeed. "First We Take Manhattan" was first recorded by Jennifer Warnes on Famous Blue Raincoat, her 1987 album of Cohen covers, whereas the man himself recorded it for his 1988 album I'm Your Man.
Watch and listen