| ID | Interpret | Skladba | Album | |
| 1. | Per Bronco Karlsson | The saddest bad I ever had | |  |
| 2. | Pernice Brothers | Saddest Quo | Discover A Lovelier You |  |
| 3. | Pernice Brothers | Saddest Quo | Discover A Lovelier You | |
| 4. | Zoe Keating | saddest.03 | Devil's Chair score | |
| 5. | Ephemera | Saddest Day | | |
| 6. | Ephemera | Saddest Day | Sun | |
| 7. | Ephemera | Saddest Day | Sun | |
| 8. | Ephemera | Saddest Day | Sun | |
| 9. | Akon | Saddest Day | Tapemasters Inc-One Man Band Man |  |
| 10. | Pernice Brothers | Saddest Quo | Discover A Lovelier You | |
| 11. | Doug Ashdown | The Saddest Song of All | The Age of Mouse | |
| 12. | Dave Britt | Saddest Song | Bent On Breaking EP | |
| 13. | Sonny Marshall | The Saddest Story | Song-poem Archived Music - Volume 8 - The Fruit of Self Control | |
| 14. | Idris Muhammad | The Saddest Thing | Power Of Soul | |
| 15. | Idris Muhammad | The Saddest Thing | Power Of Soul | |
| 16. | Dave Britt | Saddest Song | Bent On Breaking EP | |
| 17. | Red Star Belgrade | Saddest Girl | Where The Sun Doesn't Shine | |
| 18. | Red Star Belgrade | Saddest Girl | Where The Sun Doesn't Shine | |
| 19. | The Ataris | The Saddest Song | So Long Astoria | |
| 20. | The Ataris | The Saddest Song | So Long, Astoria | |
| 21. | The Ataris | Saddest Song | So Long Astoria | |
| 22. | Bellevue | The Saddest Thing | Lost In Space | |
| 23. | Bird Dog | Saddest Lion | You Are Only As Tall As The Grass Grows | |
| 24. | Red Star Belgrade | Saddest Girl | Where The Sun Doesn't Shine | |
| 25. | Sabrina Orah Mark | The Saddest Gown in the World | From the Fishouse | |
| 26. | The Magnetic Fields | The Saddest Story Ever Told | The Wayward Bus / Distant Plastic Trees | |
| 27. | Woodpigeon | The Saddest Music in the World | Live on BBC 6 Music 24-02-2009 | |
| 28. | The Lawrence Arms | The Slowest Drink At The Saddest Bar On The Snowiest Day In The Greatest City | Buttsweat and Tears | |
