38. Ryan Adams, 'Heartbreaker'
"When you're young, you get sad, then you get high," whooped Ryan Adams on his solo debut. As the leader of alt-country heroes Whiskeytown, Adams had written his fair share of songs about youth, sadness and altered states. But Heartbreaker gave these themes a classic heft, in weather-beaten country-folk songs that marked Adams as an heir to the Band and Gram Parsons. Best of all was the slow-rolling "In My Time of Need," an alternately devastating and transcendent neo-Dust Bowl ballad. "Can you take away the pain of hurtful deeds?" he sang, sounding plenty sad, but not quite so young, or so high.
• Rolling Stone's Original 2000 Review