Welcome to BillboardTop100of.com
1999
| 1 | Cher | Believe |
| 2 | TLC | No Scrubs |
| 3 | Monica | Angel Of Mine |
| 4 | Whitney Houston | Heartbreak Hotel |
| 5 | Britney Spears | …Baby One More Time |
| 6 | Sixpence None The Richer | Kiss Me |
| 7 | Christina Aguilera | Genie In A Bottle |
| 8 | Sugar Ray | Every Morning |
| 9 | Deborah Cox | Nobody’s Supposed To Be Here |
| 10 | Ricky Martin | Livin’ La Vida Loca |
| 11 | 702 | Where My Girls At? |
| 12 | Jennifer Lopez | If You Had My Love |
| 13 | Goo Goo Dolls | Slide |
| 14 | Brandy | Have You Ever? |
| 15 | Backstreet Boys | I Want It That Way |
| 16 | R. Kelly and Celine Dion | I’m Your Angel |
| 17 | Smash Mouth | All Star |
| 18 | Sarah McLachlan | Angel |
| 19 | Santana feat. Rob Thomas | Smooth |
| 20 | TLC | Unpretty |
| 21 | Destiny’s Child | Bills, Bills, Bills |
| 22 | Eagle-Eye Cherry | Save Tonight |
| 23 | Pearl Jam | Last Kiss |
| 24 | Maxwell | Fortunate |
| 25 | Backstreet Boys | All I Have To Give |
| 26 | Enrique Iglesias | Bailamos |
| 27 | Busta Rhymes feat. Janet | What’s It Gonna Be?! |
| 28 | Everlast | What It’s Like |
| 29 | Lenny Kravitz | Fly Away |
| 30 | Sugar Ray | Someday |
| 31 | Divine | Lately |
| 32 | Shania Twain | That Don’t Impress Me Much |
| 33 | Will Smith feat. Dru Hill and Kool Moe Dee | Wild Wild West |
| 34 | Red Hot Chili Peppers | Scar Tissue |
| 35 | Mariah Carey feat. Jay-Z | Heartbreaker |
| 36 | Mariah Carey | I Still Believe |
| 37 | 98 Degrees | The Hardest Thing |
| 38 | LFO | Summer Girls |
| 39 | Jay-Z feat. Amil (Of Major Coinz) and Ja | Can I Get A… |
| 40 | Third Eye Blind | Jumper |
| 41 | Lauryn Hill | Doo Wop (That Thing) |
| 42 | Lou Bega | Mambo No. 5 (A Little Bit Of…) |
| 43 | Tyrese | Sweet Lady |
| 44 | Whitney Houston | It’s Not Right But It’s Okay |
| 45 | ‘N Sync | (God Must Have Spent) A Little More Time On You |
| 46 | Shawn Mullins | Lullaby |
| 47 | 112 feat. Lil’Z | Anywhere |
| 48 | K-Ci and JoJo | Tell Me It’s Real |
| 49 | Matchbox 20 | Back 2 Good |
| 50 | Blaque | 808 |
| 51 | Tal Bachman | She’s So High |
| 52 | Ricky Martin | She’s All I Ever Had |
| 53 | Will Smith | Miami |
| 54 | Jewel | Hands |
| 55 | JT Money feat. Sole | Who Dat |
| 56 | Tim McGraw | Please Remember Me |
| 57 | Shania Twain | From This Moment On |
| 58 | Faith Evans | Love Like This |
| 59 | Jesse Powell | You |
| 60 | Total feat. Missy Elliott | Trippin’ |
| 61 | Silk | If You (Lovin’ Me) |
| 62 | Lauryn Hill | Ex-Factor |
| 63 | Jordan Knight | Give It To You |
| 64 | Goo Goo Dolls | Black Balloon |
| 65 | Eric Benet feat. Tamia | Spend My Life With You |
| 66 | Dru Hill | These Are The Times |
| 67 | Mark Chesnutt | I Don’t Want To Miss A Thing |
| 68 | 98 Degrees | I Do (Cherish You) |
| 69 | 98 Degrees | Because Of You |
| 70 | Sarah McLachlan | I Will Remember You (Live) |
| 71 | Chante Moore | Chante’s Got A Man |
| 72 | Case | Happily Ever After |
| 73 | Whitney Houston | My Love Is Your Love |
| 74 | Faith Evans feat. Puff Daddy | All Night Long |
| 75 | Juvenile feat. Mannie Fresh and Lil’ Wayne | Back That Thang Up |
| 76 | Brandy | Almost Doesn’t Count |
| 77 | Shania Twain | Man! I Feel Like A Woman! |
| 78 | Len | Steal My Sunshine |
| 79 | Marc Anthony | I Need To Know |
| 80 | Ginuwine | So Anxious |
| 81 | Case and Joe | Faded Pictures |
| 82 | Brian McKnight | Back At One |
| 83 | R. Kelly | When A Woman’s Fed Up |
| 84 | Kenny Chesney | How Forever Feels |
| 85 | Lonestar | Amazed |
| 86 | Britney Spears | Sometimes |
| 87 | Mo Thugs Family feat. Bone Thugs-N-Harmony | Ghetto Cowboy |
| 88 | Fastball | Out Of My Head |
| 89 | Jay-Z | Hard Knock Life (Ghetto Anthem) |
| 90 | Naughty By Nature feat. Zhane | Jamboree |
| 91 | BLACKstreet and Mya feat. Mase and Blinky Blink | Take Me There |
| 92 | Joey McIntyre | Stay The Same |
| 93 | Jo Dee Messina | Lesson In Leavin’ |
| 94 | Goo Goo Dolls | Iris |
| 95 | Puff Daddy feat. R. Kelly | Satisfy You |
| 96 | Citizen King | Better Days (And The Bottom Drops Out) |
| 97 | N Sync and Gloria Estefan | Music Of My Heart |
| 98 | George Strait | Write This Down |
| 99 | Whitney Houston and Mariah Carey | When You Believe |
| 100 | Alabama feat. ‘N Sync | God Must Have Spent A Little More Time On You |