Heartbreaker, released in 2000, is an album by Ryan Adams in the alternative country genre. It was recorded over 14 days at Woodland Studios in Nashville, Tennessee.

Track listing

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

Personnel

Musicians

• Ryan Adams - vocals, acoustic guitar, electric guitar, harmonica, piano, banjo
• Ethan Johns - drums, bass, chamberlin, glockenspiel, B-3 organ, vibes
• David Rawlings - vocals, acoustic guitar, electric guitar, banjo, "throws tambourine"
• Gillian Welch - vocals, banjo, acoustic guitar, electric bass, "voice of 'Lucy'"
• Pat Sansone - piano on "Oh My Sweet Carolina," chamberlin, "weird-storm-producing organ type instrument on Bartering Lines," piano on "Why Do They Leave?" and "Come Pick Me Up," "background with Ethan on 'Winding Wheel'"
• Emmylou Harris - vocals on "Oh My Sweet Carolina"
• Kim Richey - vocals on "Come Pick Me Up"
• Allison Pierce - vocals on "Why Do They Leave?"

Production

• Ethan Johns - producer, engineer, mixer
• Patrick Himes - assistant engineer
• Doug Sax - mastering
• David McClister - photography
• Gina Binkley - design