What is the longest Bruce Springsteen song?

At the start of the 1970s, Bruce Springsteen was still starting to come into his own as a songwriter. Despite being one of the most interesting voices to come out of the rock scene, his debut album, Greetings from Asbury Park, made various news outlets hail him as the modern version of a Bob Dylan figure, looking to be one of the premiere voices of the ‘70s. Springsteen had always felt uncomfortable with the Dylan tag, though, and The Wild The Innocent and The E Street Band saw him borrow more from the jazz world.

While it’s easy to call the album a sophomore slump in the commercial sense, the songs that ‘The Boss’ serves up aren’t cut out to be singles. Although ‘Kitty’s Back’ has remained a phenomenal cut whenever the E Street Band play it live, Springsteen stretches his stories out to operatic proportions, filled with detailed characters that roam the streets of New Jersey.

Towards the end of the record, Springsteen paints a vivid picture of one state on ‘New York City Serenade’. By taking the perspective of different people, The Boss tells the story of people that choose to stay where it’s comfortable for them to be, even though they know it will kill their dreams in the end.

As Billy and Jackie mess around on the wrong side of the tracks and midnight falls over Manhattan, the protagonist reaches out to the fish lady to follow him on the first train out of there. Although he has a fire in his eyes, there’s always something stopping her, afraid that that train will end up slowing her down sooner or later. 

Left cold and dejected, Springsteen asks for the band on the subway to serenade him, knowing that he will face a long ride into the unknown without someone by his side. As the rest of the band joins behind him, the instruments jam a lot more, including Clarence Clemons’ breathtaking saxophone playing and Roy Bittan’s added drama behind the piano.

Although the song needed that kind of bombast, it ended up being Springsteen’s longest song to date, standing at a crushing 9:56. While that kind of runtime seems to be reserved for prog rock epics from around the same time, Springsteen earns every minute of that runtime in his lyrical conviction and aching emotion in his every word.

This dramatic approach to storytelling would also inform his breakthrough album Born to Run, with songs like ‘Jungleland’ sprawling out across its runtime with dramatic instrumental breaks and songs that reached for the rafters. Whereas ‘New York City Serenade’ may have been a cry of desperation, the following album shows a glimmer of hope for people like Springsteen that exists right on the other side of the skyline.

This wouldn’t be the last time that Springsteen returned to the theme of New York City, either, with The Rising being an in-depth look at what ‘The Big Apple’ felt like for residents who had just gone through the perils of 9/11. New York City might be where aspiring artists like to chase their dreams, but Springsteen’s lyrics are a good reminder that that city of hope can also become a prison.

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