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Great songs are peppered throughout his solo discography, so I don't think you can make a misstep. A popular starting point still is Sailing to Philadelphia from 2000 (much better than his solo debut which came before). The title track, a duet with James Taylor, is one of the most beautiful songs of his entire career.
I like that. Hadn't heard it before.
I'd say either or both of the guys had been listening to Jimmy Webb's song The Highwayman, which is very similar in style.
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