| 1 | iTunes Originals | Fiona Apple | 0:04 |
| 2 | Tymps (The Sick in the Head Song) | Fiona Apple | 4:03 |
| 3 | I Want to Make People Happy | Fiona Apple | 4:04 |
| 4 | Never Is a Promise | Fiona Apple | 5:53 |
| 5 | It Didn’t Turn Out How I Expected It to Turn Out | Fiona Apple | 1:53 |
| 6 | Criminal (iTunes Originals version) | Fiona Apple | 4:22 |
| 7 | I Can’t Remember How I Got There | Fiona Apple | 1:22 |
| 8 | Shadowboxer (iTunes Originals version) | Fiona Apple | 6:16 |
| 9 | A 90 Word Album Title | Fiona Apple | 2:33 |
| 10 | Fast as You Can (iTunes Originals version) | Fiona Apple | 4:51 |
| 11 | Your Crowbar, So Far | Fiona Apple | 1:00 |
| 12 | I Know (iTunes Originals version) | Fiona Apple | 5:23 |
| 13 | It Was Just a Plastic Bag | Fiona Apple | 1:52 |
| 14 | Paper Bag | Fiona Apple | 3:38 |
| 15 | The Making of Extraordinary Machine | Fiona Apple | 10:28 |
| 16 | O’ Sailor | Fiona Apple | 5:35 |
| 17 | A Pep Talk to Myself | Fiona Apple | 2:04 |
| 18 | Extraordinary Machine (iTunes Originals version) | Fiona Apple | 3:51 |
| 19 | A Bird’s Eye View of All of My Relationships | Fiona Apple | 1:42 |
| 20 | Get Him Back (iTunes Originals version) | Fiona Apple | 4:56 |
| 21 | I Just Wanted to Leave | Fiona Apple | 0:39 |
| 22 | Window | Fiona Apple | 5:32 |
| 23 | Finding the Key | Fiona Apple | 2:13 |
| 24 | Better Version of Me | Fiona Apple | 3:59 |
| 25 | I’m Feeling Hopeful | Fiona Apple | 1:26 |
| 26 | Waltz (Better Than Fine) | Fiona Apple | 3:45 |