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Thompson, son of folk-rock legends Richard and Linda Thompson, developed his musical drive early in life and launched his first band while still in his early teens. By the time he released his self-titled solo debut in 2000, he'd served a stint in his father's touring band and contributed guitar and vocals to his dad's albums You? Me? Us? and Mock Tudor. He subsequently co-produced and played on his mother's 2002 comeback disc Fashionably Late, and toured as a member of Rosanne Cash's backing band.
After signing with Verve, he released his widely acclaimed 2006 sophomore album Separate Ways, which demonstrated how much his songwriting, performing and record-making skills had evolved since his debut. It was followed in 2007 by Up Front & Down Low, a collection of personally charged readings of classic American country songs that demonstrated Thompson's increased assurance as a performer and interpreter.
“My first record was made in two weeks, and I had no idea what I was doing,” Thompson states. "Separate Ways was done over a long period of time in bits and pieces. And Upfront & Down Low was done quickly and was intentionally free–swinging and loose. With the new one, we put a lot of time and effort into it, but we made it pretty quickly, because we had a plan and did a lot of preparation and pre-production. Because of that, it feels more like a complete package to me.”