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Pop Radio Top 20 | |||
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5/21/1999 | |||
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| 1 | 2 | Livin' La Vida Loca Ricky Martin | 6 |
| 2 | 3 | No Scrubs T.L.C. | 11 |
| 3 | 1 | Kiss Me Sixpence None The Richer | 12 |
| 4 | 4 | Every Morning Sugar Ray | 17 |
| 5 | 5 | What It's Like Everlast | 10 |
| 6 | 6 | The Hardest Thing 98 Degrees | 10 |
| 7 | 7 | I Want It That Way Backstreet Boys | 5 |
| 8 | 9 | That Don't Impress Me Much Shania Twain | 7 |
| 9 | 8 | Heartbreak Hotel Whitney Houston w/ Faith Evans & Kelly Price | 8 |
| 10 | 11 | Slide Goo Goo Dolls | 26 |
| 11 | 10 | Fly Away Lenny Kravitz | 13 |
| 12 | 17 | Sometimes Britney Spears | 2 |
| 13 | 12 | I Drive Myself Crazy 'N Sync | 6 |
| 14 | 18 | Give It To You Jordan Knight | 4 |
| 15 | - | Hey Leonardo (She Likes Me For Me) Blessid Union Of Souls | 1 |
| 16 | 14 | Anything But Down Sheryl Crow | 6 |
| 17 | 15 | Special Garbage | 6 |
| 18 | 13 | Believe Cher | 18 |
| 19 | - | Wild Wild West Will Smith w/ Dru Hill & Kool Moe Dee | 1 |
| 20 | 20 | Back 2 Good Matchbox 20 | 18 |