| ID | Interpret | Skladba | Album | |
| 61. | Denise Howell, Colette Vogele, Evan Brown, and Karl Susman | Denise Howell, Colette Vogele, Evan Brown, and Karl Susman - TWiL 18: Dispatches from the Electronic Frontier | TWiL October 2008 |  |
| 62. | Ila Cantor | 3. The Wrong Opinion | Live October 13, 2008 | |
| 63. | Ila Cantor | 6. Popsicle Head | Live October 13, 2008 | |
| 64. | Ila Cantor | 1. What HE Said | Live October 13, 2008 | |
| 65. | Ila Cantor | 4. Double-Think | Live October 13, 2008 | |
| 66. | Ila Cantor | 7. Quarter Notes #2 | Live October 13, 2008 | |
| 67. | The Very Rev. Alan Jones | Sermon for Sunday 11am Choral Eucharist | Sunday, October 5 2008 | |
| 68. | Denise Howell, Colette Vogele, Evan Brown, and Karl Susman | TWiL 18: Dispatches from the Electronic Frontier | TWiL October 2008 | |
| 69. | Amber MacArthur and Leo Laporte | net@night 69: My Name Is Webby | net@night October 2008 | |
| 70. | Ila Cantor | 7.Double Think | Live October 14, 2008 | |
| 71. | Wayne Pacelle | The Forum at Grace Cathedral - SF | Sunday, October 5 2008 | |
| 72. | Frontier Index | Collide | Frontier Index | |
| 73. | Carta | Bridges | An Index of Birds | |
| 74. | Charlie & Shaman | Apocalypse Radio October 26 2008 | Apocalypse Radio October 26 2008 | |
| 75. | Charlie & Shaman | Apocalypse Radio October 05 2008 | Apocalypse Radio October 05 2008 | |
| 76. | Paul Jacob | Too Darn Much Trouble? | Common Sense, October 6 - 17, 2008 | |
| 77. | Kanye West | Love Lockdown | October Hits 2008 DJ JoVy |   |
| 78. | Kanye West | Love Lockdown | October Hits 2008 DJ JoVy | |
| 79. | Paul Jacob | When Good Economists Go Bad | Common Sense, October 20 - 31, 2008 | |
| 80. | Randal Schwartz and Leo Laporte | FLOSS Weekly 45: KDE | FLOSS Weekly October 2008 | |
| 81. | Richard Armitage, Richard Allinson | Richard Armitage on The Sarah Kennedy Show | BBC Radio 2, 27th October 2008 | |
| 82. | Randal Schwartz and Leo Laporte | FLOSS Weekly 44: GNUstep | FLOSS Weekly October 2008 | |
| 83. | Randal Schwartz and Leo Laporte | FLOSS Weekly 46: SCALE | FLOSS Weekly October 2008 | |
| 84. | Paul Jacob | A Bloombergian, Buzzing Confusion | Common Sense, October 6 - 17, 2008 | |
| 85. | Ciara | Work | THE HITS OCTOBER 2008 by Melero VOL.1 | |
| 86. | Paul Thurrott with Leo Laporte | Windows Weekly 80: PDC Preview | Windows Weekly October 2008 | |
| 87. | Paul Jacob | Light Rail, Too Heavy for Developers | Common Sense, October 20 - 31, 2008 | |
| 88. | Paul jacob | Real Change at the Ballot Box | Common Sense, October 6 - 17, 2008 | |
| 89. | Paul Thurrott with Leo Laporte | Windows Weekly 78: Microsoft Strata | Windows Weekly October 2008 | |
| 90. | Keri Hilson Ft. Akon | Mic Check | October Hits 2008 DJ JoVy | |
