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| Month | Name | Ranking |
| October 31st, 1999 | Gracie Jiu-Jitsu Ate My Balls/Vs. Mr. T |
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| October 30th, 1999 | Gracie Jiu-Jitsu Ate My Balls/Vs. Mr. T |
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| October 29th, 1999 | Gracie Jiu-Jitsu Ate My Balls/Vs. Mr. T |
|
| October 28th, 1999 | Deersat: Bringing Deer To Space |
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| October 26th, 1999 | The Fart Farm |
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| October 25th, 1999 | Send-A-Turd |
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| October 20th, 1999 | Sounds of Pasta |
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| October 19th, 1999 | The Blair Witch Project... |
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| October 15th, 1999 | Egg Party |
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| October 14th, 1999 | Webingo |
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| October 13th, 1999 | Worst Of The Web Ate My Balls! |
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| October 12th, 1999 | Potato Worship |
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| October 10th, 1999 | Lord of Zucchini and Vegetable Kind |
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| October 9th, 1999 | Breast Milk Does EVERYbody Good |
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| October 8th, 1999 | Americans For Purity |
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| October 4th, 1999 | Cheese.com |
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| October 3rd, 1999 | Ulric's Pagan Circle |
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