Heartbreaker was released on Bloodshot Records in 2000.
The album is currently owned and distributed by PAX-AM.
- Superchunk cover Ryan's "Come Pick Me Up," Blitzen Trapper cover "To Be Young (Is To Be Sad, Is To Be High)," Ivan & Alyosha cover "My Winding Wheel," and Nicki Bluhm & the Gramblers cover "Oh My Sweet Carolina" on While No One Was Looking: Toasting 20 Years of Bloodshot Records
- "Amy" video on the DVD Bloodied But Unbowed
- "Bottom of the Glass" as Whiskeytown on Straight Outta Boone County
- "Silver Wings" on Poor Little Knitter on the Road
- "Monday Night" on Down to the Promised Land: 5 Years of Bloodshot Records
- "Goodbye Honey" and "To Be Young" (acoustic version) on Making Singles, Drinking Doubles
- "To Be Young" on the movie soundtrack album The Slaughter Rule
- Vocal harmonies on Alejandro Escovedo's A Man Under the Influence