| ID | Interpret | Skladba | Album | |
| 61. | Dick DeBartolo with Leo Laporte | Daily Giz Wiz 686: T-Mobile's G1 | Daily Giz Wiz October 2008 |  |
| 62. | The Very Rev. Alan Jones | Sermon for Sunday 11am Choral Eucharist | Sunday, October 5 2008 | |
| 63. | The Very Rev. Alan Jones | Sermon for Sunday 11am Choral Eucharist | Sunday, October 12 2008 | |
| 64. | Ila Cantor | 4. Double-Think | Live October 13, 2008 | |
| 65. | Dick DeBartolo with Leo Laporte | Daily Giz Wiz 690: Kodak Disc Camera | Daily Giz Wiz October 2008 | |
| 66. | Randal Schwartz and Leo Laporte | FLOSS Weekly 46: SCALE | FLOSS Weekly October 2008 | |
| 67. | Randal Schwartz and Leo Laporte | FLOSS Weekly 44: GNUstep | FLOSS Weekly October 2008 | |
| 68. | Randal Schwartz and Leo Laporte | FLOSS Weekly 45: KDE | FLOSS Weekly October 2008 | |
| 69. | Richard Armitage, Richard Allinson | Richard Armitage on The Sarah Kennedy Show | BBC Radio 2, 27th October 2008 | |
| 70. | Ciara | Work | THE HITS OCTOBER 2008 by Melero VOL.1 |  |
| 71. | Paul Thurrott with Leo Laporte | Windows Weekly 78: Microsoft Strata | Windows Weekly October 2008 | |
| 72. | Leo Laporte, Andy Ihnatko , Sc | MacBreak Weekly 109: Steve Liv | MacBreak Weekly October 2008 | |
| 73. | Paul Jacob | Too Darn Much Trouble? | Common Sense, October 6 - 17, 2008 | |
| 74. | Paul Jacob | A Bloombergian, Buzzing Confusion | Common Sense, October 6 - 17, 2008 | |
| 75. | Paul Thurrott with Leo Laporte | Windows Weekly 79: He's A Biter | Windows Weekly October 2008 | |
| 76. | Paul jacob | Real Change at the Ballot Box | Common Sense, October 6 - 17, 2008 | |
| 77. | Paul Jacob | Light Rail, Too Heavy for Developers | Common Sense, October 20 - 31, 2008 | |
| 78. | Charlie & Shaman | Apocalypse Radio October 26 2008 | Apocalypse Radio October 26 2008 | |
| 79. | Paul Jacob | A Barney Frank Appraisal | Common Sense, October 6 - 17, 2008 | |
| 80. | Charlie & Shaman | Apocalypse Radio October 05 2008 | Apocalypse Radio October 05 2008 | |
| 81. | Keri Hilson Ft. Akon | Mic Check | October Hits 2008 DJ JoVy | |
| 82. | Paul Jacob | When Good Economists Go Bad | Common Sense, October 20 - 31, 2008 | |
| 83. | Kanye West | Love Lockdown | October Hits 2008 DJ JoVy |  |
| 84. | Kanye West | Love Lockdown | October Hits 2008 DJ JoVy | |
| 85. | Paul Thurrott with Leo Laporte | Windows Weekly 80: PDC Preview | Windows Weekly October 2008 | |
| 86. | Paul Thurrott with Leo Laporte | Windows Weekly 81: Windows 7 and Azure | Windows Weekly October 2008 | |
| 87. | Elliott Brood | Lookin' For A Love | Grad Club, Kingston, 12 October 2008 | |
| 88. | Elliott Brood | Write It All Down For You | Grad Club, Kingston, 12 October 2008 | |
| 89. | Carrie Dahlby | Hazy Shade of Killer | The FuMP Volume 11: September-October 2008 | |
| 90. | Elliott Brood | Oh Alberta | Grad Club, Kingston, 12 October 2008 | |
