Mason Jennings is in no way related to late outlaw country artist Waylon Jennings, which means he is also not related to Shooter. Mason didn’t even come up in a music-making family, but he picked up the guitar at 13, dropped out of school at 16 to pursue a musical career, and self-produced and released his self-titled debut at 22, in 1997. More than two decades and a few dozen recordings later, he’s seen high highs and low lows—divorce, battles with depression and agoraphobia, and, most importantly, a new love that inspired the songwriting on last year’s Songs from When We Met. It’s folk-pop encased in a golden sheen of contentment—warm, breezy, and quite lovely, as driven by Jennings’s gentle, reedy, vaguely Bob Dylan–reminiscent vocal quality. by Leilani Polk