Heartbreaker is the debut solo studio album by Ryan Adams, originally released September 5, 2000 on Bloodshot Records. The album was recorded over fourteen days at Woodland Studios in Nashville, Tennessee and has since established itself as one of alt-country’s most iconic records.

1. Argument With David Rawlings Concerning Morrissey
2. To Be Young (is To Be Sad, is To Be High)
3. My Winding Wheel
4. Amy
5. Oh My Sweet Carolina
6. Bartering Lines
7. Call Me On Your Way Back Home
8. Damn, Sam (I Love a Woman That Rains)
9. Come Pick Me Up
10. To Be the One
11. Why Do They Leave?
12. Shakedown On 9th Street
13. Don't Ask For the Water
14. In My Time of Need
15. Sweet Lil Gal (23rd/1st)