The first time I heard this song, it became the soundtrack to a difficult and depressing period in my life. It was 2009, and I was going through a prolonged break-up. I was living far from my family and was generally lamenting life amongst the emotionally desolate environment of a big city.

The song's lyrics – which described a young man turning his back on his family and leaving home, only to learn years later that his mother had died and that he couldn't bring himself to return home in his current, impoverished state – led to many deep, sorrowful sighs that came emanating from my diaphragm as I listened to the track on long train commutes around Sydney.

The version I first felt a connection with, however, was not Dylan's but instead was a cover performed by British vocalist, Antony, and The National guitarist, Bryce Dessner, for the fantastic 2009 charity compilation album, Dark Was The Night.

The song's dark and murky undertones pulsed with sadness, a longing for lost loved ones, and a desire for a simpler life. It struck a chord with my overly emotional frame of mind, and at the time I accredited that to the brilliance of Antony and Dessner in their performance of the piece.

Upon hearing Dylan's beautifully simple rendition, however, laden with his gentle acoustic picking and hushed vocals; and then also learning that Dylan's version was a reinterpretation of the classic folk tune 'Nine hundred Miles'; my understanding of the universal and enduring appeal of this song and it's context was forever altered.

It made me realize that regardless of the performer, this song carries the weight of generations of heartbreak, and no matter how you play it, those emotional ancestors dig their way to the surface.

I'm sure a young Bob Dylan felt that weight when he recorded his version in a Minneapolis apartment in 1962. As I'm sure that same sense of loss and longing connected with Antony and Dessner when they chose to give the tune a new breath of life many years later.

'I was young when I left home' has definitely left a lasting impression on many throughout history, including a journalist in his mid 20′s from Sydney. And it's that enduring legacy that makes me believe that as long as there is heartbreak and homesickness out there, this track will continue to rear its sad head throughout musical history for many chapters to come.