| Rank | Song | Artist | Points | |
| 150 |  |
Bring It All To Me | Blaque | 72 |
| 149 |  |
Baby One More Time | Britney Spears | 85 |
| 148 |  |
Get It On Tonight | Montell Jordan | 86 |
| 147 |  |
The Power Of Goodbye | Madonna | 90 |
| 146 |  |
Home Alone | R Kelly f/ Keith Murray | 98 |
| 145 |  |
Rhythm Divine | Enrique Iglesias | 100 |
| 144 |  |
Slide | Goo Goo Dolls | 100 |
| 143 |  |
You Are Everything (Remix) | Dru Hill f/ Ja Rule | 101 |
| 142 |  |
If You (Lovin' Me) | Silk | 102 |
| 141 |  |
Ruff Ryders' Anthem | DMX | 107 |
| 140 |  |
Fire Escape | Fastball | 114 |
| 139 |  |
Inside Out | Eve 6 | 115 |
| 138 |  |
The Greatest Romance Ever Sold (Remix) | The Artist f/ Eve | 116 |
| 137 |  |
Because Of You | 98 Degrees | 116 |
| 136 |  |
C'est La Vie | B*Witched | 122 |
| 135 |  |
Angels | Robbie Williams | 137 |
| 134 |  |
U Don't Know Me Like U Used To (Remix) | Brandy f/ Shaunta & Da Brat | 141 |
| 133 |  |
If I Could Turn Back The Hands Of Time | R. Kelly | 148 |
| 132 |  |
Father Of Mine | Everclear | 149 |
| 131 |  |
Georgy Porgy | Eric Benét f/ Faith Evans | 153 |
| 130 |  |
U Know What's Up (Remix) | Donell Jones f/ Left Eye | 157 |
| 129 |  |
Why Don't You Get A Job? | Offspring | 157 |
| 128 |  |
You've Got A Way (from Notting Hill) |
Shania Twain | 161 |
| 127 |  |
Doo Wop (That Thing) | Lauryn Hill | 162 |
| 126 |  |
Everybody's Free (To Wear Sunscreen) | Baz Luhrmann f/ Lee Perry | 166 |
| 125 | |
Nothing Really Matters | Madonna | 176 |
| 124 |  |
Hope (from For Love Of The Game) |
Shaggy | 177 |
| 123 |  |
When You Believe (from Prince Of Egypt) |
Whitney Houston & Mariah Carey | 178 |
| 122 |  |
Life (from Life) |
K-Ci & Jo Jo | 187 |
| 121 |  |
Got Your Money | O.D.B. f/ Kelis | 192 |
| 120 |  |
Bling Bling | B.G. | 196 |
| 119 |  |
Rosa Parks | Outkast | 205 |
| 118 |  |
Give It To You | Jordan Knight | 216 |
| 117 |  |
Jumper | Third Eye Blind | 217 |
| 116 |  |
Will 2K | Will Smith f/ K-Ci | 218 |
| 115 |  |
Then The Morning Comes | Smash Mouth | 229 |
| 114 |  |
Everything Is Everything | Lauryn Hill | 237 |
| 113 |  |
The Animal Song (from The Other Sister) |
Savage Garden | 240 |
| 112 | |
Millennium | Robbie Williams | 243 |
| 111 | |
Meeting In My Bedroom | Silk | 250 |
| 110 |  |
Get Gone (Get The Hell On) | Ideal | 252 |
| 109 |  |
Luv Me, Luv Me (from How Stella Got Her Groove Back) |
Shaggy f/ Janet | 255 |
| 108 |  |
It's All Been Done | Barenaked Ladies | 260 |
| 107 |  |
Lay Down (Candles In The Rain) | Meredith Brooks f/ Queen Latifah | 267 |
| 106 |  |
Knock On Wood (from 54) |
Mary Griffin | 268 |
| 105 |  |
Touch It | Monifah | 281 |
| 104 |  |
Good To Be Alive (from Go) |
DJ Rap | 284 |
| 103 |  |
Faded Pictures (from Rush Hour) |
Case f/ Joe | 286 |
| 102 | |
Did You Ever Think? | R Kelly | 288 |
| 101 |  |
It's The Things You Do | Five | 293 |
Top 150 Songs Of 1999 (100-51)
