| 1 | iTunes Originals | Lee Ann Womack | 0:06 |
| 2 | He Oughta Know That by Now | Lee Ann Womack | 3:41 |
| 3 | The First 17 Years of My Life (Interview) | Lee Ann Womack | 1:20 |
| 4 | Am I the Only Thing That You’ve Done Wrong | Lee Ann Womack | 3:48 |
| 5 | A Really Cool Way to Launch My Career (Interview) | Lee Ann Womack | 1:48 |
| 6 | Never Again, Again (iTunes Originals version) | Lee Ann Womack | 3:34 |
| 7 | It’ll Be Your First #1 (Interview) | Lee Ann Womack | 0:40 |
| 8 | The Fool (iTunes Originals version) | Lee Ann Womack | 3:48 |
| 9 | One for the Girls (Interview) | Lee Ann Womack | 0:33 |
| 10 | I’ll Think of a Reason Later (iTunes Originals version) | Lee Ann Womack | 2:55 |
| 11 | This Time It Was Personal (Interview) | Lee Ann Womack | 1:16 |
| 12 | I Hope You Dance (iTunes Originals version) | Lee Ann Womack | 3:45 |
| 13 | I Love Great Melodies (Interview) | Lee Ann Womack | 0:22 |
| 14 | Does My Ring Burn Your Finger | Lee Ann Womack | 3:28 |
| 15 | A Very, Very Good Person (Interview) | Lee Ann Womack | 0:51 |
| 16 | Mendocino Country Line | Willie Nelson with Lee Ann Womack | 4:32 |
| 17 | You Better Sit Down (Interview) | Lee Ann Womack | 0:57 |
| 18 | I May Hate Myself in the Morning (iTunes Originals version) | Lee Ann Womack | 3:11 |
| 19 | Pasty in Blue (Interview) | Lee Ann Womack | 0:35 |
| 20 | She’s Got You (iTunes Originals version) | Lee Ann Womack | 4:33 |
| 21 | Get a Key and Cut It (Interview) | Lee Ann Womack | 0:26 |
| 22 | Someone I Used to Know (non-album version) | Lee Ann Womack | 2:26 |
| 23 | I Intend to Have More Fun (Interview) | Lee Ann Womack | 0:56 |
| 24 | Something Worth Leaving Behind | Lee Ann Womack | 3:48 |