01. Randy Travis - Hard Rock Bottom of Your Heart 02. Gram Parsons - Brand New Heartache 03. Anita Cochran, Conway Twitty - (I Wanna Hear) a Cheatin'' Song (feat. Conway Twitty) 04. Deana Carter - Crying 05. Kris Kristofferson - For the Good Times 06. Michelle Branch - Ready to Let You Go 07. Marty Stuart - Drifting Apart 08. Gabby Barrett - I Will Always Love You 09. Tracy Lawrence - Can''t Break It to My Heart 10. John Anderson - I Just Came Home to Count the Memories 11. Chris Hillman - My Baby''s Gone 12. Chris Cummings - The Kind of Heart That Breaks 13. David Ball - Down at the Bottom of a Broken Heart 14. Kelly Willis - Find Another Fool 15. James Otto - Let''s Just Let Go 16. Carlene Carter - Love Is Gone 17. Tim O''Brien - Every Tear Has a Reason Why 18. Beth Nielsen Chapman - Only So Many Tears 19. Dusty Drake - One Last Time 20. The Great Divide - Out of Love 21. Highway 101 - River of Tears 22. Sissy Spacek - Hangin'' up My Heart 23. The Seldom Scene - Lost In a Memory 24. Daryle Singletary - My Heart''s Too Broke (To Pay Attention) 25. Donna Fargo - That Was Yesterday 26. The JaneDear Girls - Lucky You 27. Billy Joe Royal - A Place for the Heartache 28. Regina Regina - The Big Bad Broken Heart 29. Lace - I Cry Real Tears 30. Daron Norwood - Honky Tonk Heartache of the Year