| 1 | Have You Ever?Brandy | 1 | Chart history → |
| 2 | Nobody's Supposed To Be HereDeborah Cox | 2 | Chart history → |
| 3 | ...Baby One More TimeBritney Spears | 4 | Chart history → |
| 4 | I'm Your AngelR. Kelly & Celine Dion | 3 | Chart history → |
| 5 | Save TonightEagle-Eye Cherry | 8 | Chart history → |
| 6 | HandsJewel | 11 | Chart history → |
| 7 | LullabyShawn Mullins | 7 | Chart history → |
| 8 | LatelyDivine | 5 | Chart history → |
| 9 | Doo Wop (That Thing)Lauryn Hill | 9 | Chart history → |
| 10 | SlideGoo Goo Dolls | 14 | Chart history → |
| 11 | Trippin'Total Featuring Missy Elliott | 10 | Chart history → |
| 12 | JumperThird Eye Blind | 15 | Chart history → |
| 13 | AngelSarah McLachlan | 18 | Chart history → |
| 14 | Take Me ThereBLACKstreet & Mya Featuring Mase & Blinky Blink | 17 | Chart history → |
| 15 | From This Moment OnShania Twain | 12 | Chart history → |
| 16 | Love Like ThisFaith Evans | 13 | Chart history → |
| 17 | Because Of You98 Degrees | 6 | Chart history → |
| 18 | MiamiWill Smith | 23 | Chart history → |
| 19 | Can I Get A...Jay-Z Featuring Amil (Of Major Coinz) & Ja | 19 | Chart history → |
| 20 | IrisGoo Goo Dolls | 20 | Chart history → |
| 21 | These Are The TimesDru Hill | 26 | Chart history → |
| 22 | Angel Of MineMonica | 31 | Chart history → |
| 23 | (God Must Have Spent) A Little More Time On You'N Sync | 30 | Chart history → |
| 24 | I Don't Want To Miss A ThingMark Chesnutt | 24 | Chart history → |
| 25 | When You BelieveWhitney Houston & Mariah Carey | 64 | Chart history → |
| 26 | Ghetto CowboyMo Thugs Family Featuring Bone Thugs-N-Harmony | 21 | Chart history → |
| 27 | This KissFaith Hill | 16 | Chart history → |
| 28 | I'll BeEdwin McCain | 22 | Chart history → |
| 29 | My Favorite MistakeSheryl Crow | 25 | Chart history → |
| 30 | Too CloseNext | 27 | Chart history → |
| 31 | Inside OutEve 6 | 28 | Chart history → |
| 32 | Changes2Pac | 43 | Chart history → |
| 33 | Touch ItMonifah | 32 | Chart history → |
| 34 | How Deep Is Your LoveDru Hill Featuring Redman | 29 | Chart history → |
| 35 | BelieveCher | 52 | Chart history → |
| 36 | Wrong AgainMartina McBride | 45 | Chart history → |
| 37 | You Get What You GiveNew Radicals | 38 | Chart history → |
| 38 | Stand Beside MeJo Dee Messina | 51 | Chart history → |
| 39 | Fly AwayLenny Kravitz | 41 | Chart history → |
| 40 | When A Woman's Fed UpR. Kelly | 58 | Chart history → |
| 41 | There You Have ItBlackHawk | 44 | Chart history → |
| 42 | Are You That Somebody?Aaliyah | 33 | Chart history → |
| 43 | Right On The MoneyAlan Jackson | 46 | Chart history → |
| 44 | Spirit Of A Boy, Wisdom Of A ManRandy Travis | 48 | Chart history → |
| 45 | For A Little WhileTim McGraw | 56 | Chart history → |
| 46 | Every MorningSugar Ray | 66 | Chart history → |
| 47 | One WeekBarenaked Ladies | 36 | Chart history → |
| 48 | I Will Get ThereBoyz II Men | 76 | Chart history → |
| 49 | For You I WillAaron Tippin | 49 | Chart history → |
| 50 | You're Beginning To Get To MeClay Walker | 47 | Chart history → |
| 51 | It's All Been DoneBarenaked Ladies | 57 | Chart history → |
| 52 | Hard Knock Life (Ghetto Anthem)JAY-Z | 39 | Chart history → |
| 53 | Pretty Fly (For A White Guy)The Offspring | 53 | Chart history → |
| 54 | No Place That FarSara Evans | 60 | Chart history → |
| 55 | Ex-FactorLauryn Hill | 82 | Chart history → |
| 56 | Rosa ParksOutKast | 61 | Chart history → |
| 57 | Hold On To MeJohn Michael Montgomery | 65 | Chart history → |
| 58 | Heartbreak HotelWhitney Houston Feat. Faith Evans & Kelly Price | 77 | Chart history → |
| 59 | UnbelievableDiamond Rio | 74 | Chart history → |
| 60 | You're Easy On The EyesTerri Clark | 55 | Chart history → |
| 61 | Back 2 Goodmatchbox 20 | 71 | Chart history → |
| 62 | Thank UAlanis Morissette | 42 | Chart history → |
| 63 | Wrong NightReba | 70 | Chart history → |
| 64 | What It's LikeEverlast | 69 | Chart history → |
| 65 | GoodbyeSpice Girls | 37 | Chart history → |
| 66 | Hold MeBrian McKnight Featuring Tone & Kobe Bryant | 50 | Chart history → |
| 67 | Silly HoTLC | 85 | Chart history → |
| 68 | Sweetest ThingU2 | 63 | Chart history → |
| 69 | Love Me112 Featuring Mase | 34 | Chart history → |
| 70 | The Power Of Good-ByeMadonna | 54 | Chart history → |
| 71 | Fly (The Angel Song)The Wilkinsons | 72 | Chart history → |
| 72 | Faded PicturesCase & Joe | 79 | Chart history → |
| 73 | Pushin' WeightIce Cube Featuring Mr. Short Khop | 59 | Chart history → |
| 74 | Angel In DisguiseBrandy | 83 | Chart history → |
| 75 | You Were MineDixie Chicks | — | Chart history → |
| 76 | Busy ManBilly Ray Cyrus | — | Chart history → |
| 77 | Father Of MineEverclear | 75 | Chart history → |
| 78 | Never ThereCake | 78 | Chart history → |
| 79 | Luv Me, Luv MeShaggy Featuring Janet | 84 | Chart history → |
| 80 | That Don't Impress Me MuchShania Twain | — | Chart history → |
| 81 | Home AloneR. Kelly Featuring Keith Murray | 81 | Chart history → |
| 82 | Let Me Let GoFaith Hill | 73 | Chart history → |
| 83 | Someone You Used To KnowCollin Raye | 62 | Chart history → |
| 84 | Sweet LadyTyrese | — | Chart history → |
| 85 | Powerful ThingTrisha Yearwood | — | Chart history → |
| 86 | It Must Be LoveTy Herndon | 88 | Chart history → |
| 87 | All The Places (I Will Kiss You)Aaron Hall | 68 | Chart history → |
| 88 | A Bitter EndDeryl Dodd | 96 | Chart history → |
| 89 | Somebody's Out There WatchingThe Kinleys | — | Chart history → |
| 90 | MeanwhileGeorge Strait | — | Chart history → |
| 91 | Hot SpotFoxy Brown | — | Chart history → |
| 92 | Celebrity SkinHole | 91 | Chart history → |
| 93 | Husbands And WivesBrooks & Dunn | 86 | Chart history → |
| 94 | Fire EscapeFastball | 92 | Chart history → |
| 95 | Big Big WorldEmilia | — | Chart history → |
| 96 | Talk Show Shhh!Shae Jones | 99 | Chart history → |
| 97 | Wherever You GoVoices Of Theory | 87 | Chart history → |
| 98 | Come And Get With MeKeith Sweat Featuring Snoop Dogg | 89 | Chart history → |
| 99 | My Little SecretXscape | 95 | Chart history → |
| 100 | Just The Two Of UsWill Smith | 94 | Chart history → |