October 17th, 1999
Show #99
| 1:00am | ||
| ARTIST | SONG | ALBUM |
| John Jennings | Walking To China | Buddy |
| Paul McCartney | Try Not TO Cry | Run Devil Run |
| Eric Clapton | (I) Get Lost | Clapton Chronicles: The Best Of Eric Clapton |
| Willie Nelson with Emmylou Harris and Daniel Lanois | Darkness On The Face Of The Earth | Teatro |
| Sheryl Crow | If It Makes You Happy(live) | Woodstock '99 |
| Lyle Lovett | Penguins(live) | Live In Texas |
| Liquid Soul | Threadin' The Needle | Make Some Noise |
| 2:00am | ||
| ARTIST | SONG | ALBUM |
| Me'Shell Ndege'ocello | Loyalty | Bitter |
| Marie Wilson | Next Time | Real Life |
| Melissa Etheridge | Angels Would Fall | Breakdown |
| Don Henley | Gimmie What You Got | The End Of The Innoncence |
| Bruce Hornsby | Resting Place(live) | Woodstock '99 |
| Indigo Girls | Peace Tonight | Come On Now Social |
| Jude Cole | Heart Of Blues | A View From 3rd Street |
| Linda Ronstadt and Emmylou Harris | Western Wall | Western Wall: The Tuscon Sessions |
October 17th, 1999
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