| Rank | Song | Artist | Points | |
| 50 |  |
Almost Doesn't Count | Brandy | 555 |
| 49 |  |
You Got Me | The Roots f/ Erykah Badu & Eve | 556 |
| 48 |  |
Girls' Best Friend (from Blue Streak) |
Jay-Z | 558 |
| 47 |  |
Someday | Sugar Ray | 573 |
| 46 |  |
Vivrant Thing | Q-Tip | 575 |
| 45 |  |
We Can't Be Friends | Deborah Cox & R.L. | 578 |
| 46 |  |
All I Have To Give | Backstreet Boys | 587 |
| 43 |  |
Smooth | Santana f/ Rob Thomas | 590 |
| 42 |  |
My Love Is Your Love | Whitney Houston | 590 |
| 41 |  |
Miami | Will Smith | 596 |
| 40 |  |
Happily Ever After | Case | 605 |
| 39 |  |
Changes | 2 Pac | 608 |
| 38 |  |
Bailamos | Enrique Iglesias | 613 |
| 37 |  |
When A Woman's Fed Up | R Kelly | 615 |
| 36 |  |
All Star | Smash Mouth | 617 |
| 35 |  |
Bills Bills Bills | Destiny's Child | 624 |
| 34 |  |
Hate Me Now | Nas f/ Puff Daddy | 627 |
| 33 |  |
Ex-Factor | Lauryn Hill | 628 |
| 32 |  |
Every Morning | Sugar Ray | 631 |
| 31 |  |
Tell Me It's Real | K-Ci & Jo Jo | 637 |
| 30 |  |
I Do (Cherish You) (from Notting Hill) |
98 Degrees | 649 |
| 29 |  |
My First Night With You | Mya | 652 |
| 28 |  |
Can I Get A...? (from Rush Hour) |
Jay-Z f/ Amil & Ja Rule | 658 |
| 27 |  |
Have You Ever? | Brandy | 665 |
| 26 | |
Nobody's Supposed To Be Here | Deborah Cox | 673 |
| 25 |  |
If You Buy This Record Your Life Will Be Better | The Tamperer f/ Maya | 680 |
| 24 |  |
Steal My Sunshine | Len | 701 |
| 23 |  |
If You Had My Love | Jennifer Lopez | 704 |
| 22 |  |
Unpretty | TLC | 709 |
| 21 | |
Heartbreak Hotel | Whitney Houston f/ Faith Evans & Kelly Price | 723 |
| 20 |  |
Mambo No. 5 | Lou Bega | 737 |
| 19 |  |
We Like To Party | Vengaboys | 743 |
| 18 |  |
I Want It That Way | Backstreet Boys | 743 |
| 17 | |
I'm Good At Being Bad | TLC | 743 |
| 16 |  |
Believe | Cher | 755 |
| 15 |  |
Fortunate (from Life) |
Maxwell | 760 |
| 14 |  |
Spend My Life With You | Eric Benét & Tamia | 772 |
| 13 |  |
What It's Like | Everlast | 778 |
| 12 |  |
Fly Away | Lenny Kravitz | 778 |
| 11 |  |
Angel Of Mine | Monica | 779 |
| 10 |  |
Wild Wild West (from Wild Wild West) |
Will Smith f/ Dru Hill & Kool Moe Dee | 782 |
| 9 |  |
That Don't Impress Me Much | Shania Twain | 803 |
| 8 |  |
Genie In A Bottle | Christina Aguilera | 807 |
| 7 |  |
Anywhere | 112 f/ Lil' Zane | 815 |
| 6 |  |
Livin' La Vida Loca | Ricky Martin | 838 |
| 5 |  |
As | George Michael & Mary J. Blige | 841 |
| 4 | |
No Scrubs | TLC | 851 |
| 3 |  |
Where My Girls At? | 702 | 917 |
| 2 |  |
What's It Gonna Be? | Busta Rhymes f/ Janet | 1010 |
| 1 |  |
Sweet Lady | Tyrese | 1179 |
Music Central's Top 150 Songs Of 1999 (100-51)
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