Weekly Pop Top 30 for October 23, 1999 |
| LW | TW | peaks: | rock | pop |
| 3 | 1 | Heartbreaker | ▲ |
| Mariah Carey Featuring Jay-Z |
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| 1 | 2 | (You Drive Me) Crazy | 1 |
| Britney Spears |
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| 4 | 3 | Smooth | 10 | 1 |
| Santana Featuring Rob Thomas |
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| 9 | 4 | Back At One | 1 |
| Brian McKnight |
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| 8 | 5 | Waiting For Tonight | 1 |
| Jennifer Lopez |
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| 5 | 6 | My Love Is Your Love | 3 |
| Whitney Houston |
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| 2 | 7 | I Need To Know | 2 |
| Marc Anthony |
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| 11 | 8 | Man! I Feel Like A Woman! | ▲ |
| Shania Twain |
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| 7 | 9 | Mambo No. 5 (A Little Bit Of...) | 2 |
| Lou Bega |
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| 16 | 10 | The Rockafeller Skank | 11 | 6 |
| Fatboy Slim |
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| 6 | 11 | Music Of My Heart | 1 |
| 'NSYNC & Gloria Estefan |
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| 17 | 12 | I Wanna Love You Forever | 1 |
| Jessica Simpson |
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| 22 | 13 | Girl On TV | 3 |
| LFO |
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| 15 | 14 | Unpretty | 1 |
| TLC |
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| 12 | 15 | Larger Than Life | 2 |
| Backstreet Boys |
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| 10 | 16 | If I Could Turn Back The Hands Of Time | 10 |
| R. Kelly |
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| 21 | 17 | Shake Your Bon-Bon | 6 |
| Ricky Martin |
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| 25 | 18 | Satisfy You | 5 |
| Puff Daddy Featuring R. Kelly |
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| 13 | 19 | There She Goes | 13 |
| Sixpence None The Richer |
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| - | 20 | Haya Doin? | 16 |
| Carmanooch And Joey |
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| 27 | 21 | Cowboy | 4 | 15 |
| Kid Rock |
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| 19 | 22 | Angels Would Fall | 19 |
| Melissa Etheridge |
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| 14 | 23 | We Can't Be Friends | 11 |
| Deborah Cox With R.L. |
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| 23 | 24 | Genie In A Bottle | 1 |
| Christina Aguilera |
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| 18 | 25 | Back That Thang Up | 18 |
| Juvenile Featuring Manny Fresh & Lil Wayne |
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| - | 26 | All The Small Things | 1 | 1 |
| Blink 182 |
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| 24 | 27 | She's All I Ever Had | 2 |
| Ricky Martin |
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| - | 28 | Vivrant Thing | 27 |
| Q-Tip |
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| - | 29 | Will 2K | 2 |
| Will Smith |
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| - | 30 | I Knew I Loved You | 1 |
| Savage Garden |
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| Prior Week | Next Week |