As a founding member of the band Whiskeytown, Ryan Adams was considered one of alt-country's most skilled, mercurial talents when he entered the studio to record this solo debut. Tracked in Nashville in two weeks and featuring contributions from Dave Rawlings, Gillian Welch, and Emmylou Harris, Heartbreaker is a stunner. It contains two of Adams' most enduring tunes—the shambling "To Be Young (Is to Be Sad, Is to Be High)," and the, well, heartbreaking "Come Pick Me Up," a paean to the recklessness of young love. But there's not a bad song here. "My Winding Wheel" is sweeping alt-folk, "Amy" is a sweet orchestral ballad, and "Shakedown on 9th Street" is crunchy dancehall rock. Heartbreaker is a classic, hands down.