One of the greatest duets of James Taylor’s career: “You couldn’t lose”

When looking at the pinnacle of the singer-songwriter boom, it’s hard to think of any names that exceed the unmatched talents of a certain James Taylor.

In terms of establishing a strong sense of voice with emotional intricacies and nuances, Taylor was about as good as it gets, such that many of those who emerged during this era later credited him with helping them to shape their own sound, and those who managed to work with him, like Carole King, would even go so far as to say that he was the catalyst that encouraged them to pursue their own path.

Others would have their own reasons for Taylor being the epitome of a songwriter, such as, for Paul Simon, the magic came from his tone of voice and his ability to tell an entire story with melody alone, something he carried in his own work, especially when it came to how those dynamics intertwined with the broader arrangements to create something familiar-sounding but also fresh in its own way.

This was another aspect of Taylor’s music that resonated with others: he could sometimes sound like a million things at once, while also something unique in itself, building something uniquely his from extracting bits and pieces from others. His primary influences were the usual suspects, ranging from Joni Mitchell to Bob Dylan, but even those he considered the best saw someone like him and felt the same way.

Dylan, for one, once said that he couldn’t compare himself to Taylor if he tried. “I still don’t consider myself in the same realm as someone like James Taylor or Randy Newman, someone who, in my book, is a ‘songwriter for the times’,” he once said, “I feel my stuff is very hard-edged and not everybody’s cup of tea.”

While those differences are legitimate, Taylor’s music was seen by many as more broadly appealing than the rougher voices like Dylan’s, likely because the former’s music was honest in a different way, less affected by convoluted trains of thought or pepperings of self-effacing, subtle humour. He also demonstrated a good level of humility, especially when observing the broader scene and noting how players like King contributed to changing the entire landscape.

For Taylor, King was the epitome of what Dylan would call “a songwriter for the times”, and according to him, she didn’t wholly believe in her own craft at first, and appeared in the scene a little “tentative”. However, with his backing and after some consistent coaxing, King stepped out, and her uncertainty faded away as she allowed the music to speak for itself. 

Taylor and King’s most notable collaboration was, of course, her career-defining hit ‘You’ve Got a Friend’; however, one of the first moments Taylor recalled feeling enchanted was when she performed ‘Up on the Roof’ before her major explosion onto the scene, and he was able to envision the kind of artist she could be if she had the confidence to do it.

The pair delivered a special duet of the song later during their reunion in 2010, a full-circle moment, especially since Taylor had such a hand in shaping the trajectory of King’s career. “The first time that she stepped up in the context of my set was when she sang ‘Up on the Roof’ at Queen’s College,” Taylor recalled, “She was very tentative, but the music takes over, and those songs that she wrote are such vehicles, you just can’t lose. Once you hook into it, it’s away we go.” 

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