Soon before Willie Watson turned 18, he met God in an apple orchard. Or at the very least, he met there a man named Ruby Love, the older friend of a high-school buddy who had an enormous Martin guitar and a seemingly bigger understanding of the American folk songbook. Watson was existentially thirsty: A high-school dropout from upstate New York’s Finger Lakes, he was fast on his way to his first heartbreak and in a first band that didn’t take itself seriously enough. But that night in an apple orchard that had always seemed magical, at a graduation party for one of his bandmates and best friends, Watson and Love sang a few of those old songs together — ‘Worried Man Blues’ and ‘Tennessee Waltz.’ It was the first time Watson had cried while singing, the first time he had made the connection between making music and making sense of his life. He never saw Ruby Love again, but within months of that foundational 1997 rendezvous, he met the musicians with whom he’d soon start Old Crow Medicine Show. Call it revelation, fate, resurrection, whatever you will; for Watson, more than a quarter-century later, it was a duet with the divine.

‘Real Love’ harkens back to those days in rural New York, with Watson opening himself to the wreckage that comes with falling for someone for the first time. He is fragile but resolute here, pressing on in spite of vestigial pain. ‘Sad Song’ thrums like some muted and modern Jimmie Rodgers number, as Watson tries to play-act happiness one more time for a society that’s just wanted him to grin and sing. Echoing the rippling and beautiful despair of Gordon Lightfoot, the gorgeous ‘Play It One More Time’ examines the fleeting salve of music itself, or how the help it gives us can fade when we’re not truly hearing. This Is Pop? today’s song of the day is here for you.