Since 2000 was the final year of the 1990s, there having been no year zero, and the actual factual millenium beginning on 01.01.2001, I'm suggesting Ryan Adams's debut Heartbreaker. The follow-up Gold is even better, but is disqualified by dint of its 2001 release date. He went through a period of releasing EVERYTHING he wrote, with the quality control fader at zero, and his form dipped a bit as a result. He's been a **** too, but his talent is bigger than Ash Taylor's Pumas.