| 1 | If You Had My LoveJennifer Lopez | 2 | Chart history → |
| 2 | Livin' La Vida LocaRicky Martin | 1 | Chart history → |
| 3 | No ScrubsTLC | 3 | Chart history → |
| 4 | FortunateMaxwell | 4 | Chart history → |
| 5 | Where My Girls At?702 | 6 | Chart history → |
| 6 | Kiss MeSixpence None The Richer | 5 | Chart history → |
| 7 | That Don't Impress Me MuchShania Twain | 8 | Chart history → |
| 8 | 808Blaque | 10 | Chart history → |
| 9 | Who DatJT Money Featuring Sole | 7 | Chart history → |
| 10 | Chante's Got A ManChante Moore | 11 | Chart history → |
| 11 | I Want It That WayBackstreet Boys | 13 | Chart history → |
| 12 | Give It To YouJordan Knight | 12 | Chart history → |
| 13 | Every MorningSugar Ray | 9 | Chart history → |
| 14 | Wild Wild WestWill Smith Featuring Dru Hill & Kool Mo Dee | 16 | Chart history → |
| 15 | BelieveCher | 14 | Chart history → |
| 16 | Please Remember MeTim McGraw | 18 | Chart history → |
| 17 | SlideGoo Goo Dolls | 20 | Chart history → |
| 18 | Anywhere112 Featuring Lil'z | 17 | Chart history → |
| 19 | What It's LikeEverlast | 19 | Chart history → |
| 20 | Almost Doesn't CountBrandy | 22 | Chart history → |
| 21 | It's Not Right But It's OkayWhitney Houston | 32 | Chart history → |
| 22 | The Hardest Thing98 Degrees | 23 | Chart history → |
| 23 | Heartbreak HotelWhitney Houston Feat. Faith Evans & Kelly Price | 15 | Chart history → |
| 24 | All StarSmash Mouth | 27 | Chart history → |
| 25 | Sweet LadyTyrese | 21 | Chart history → |
| 26 | Happily Ever AfterCase | 69 | Chart history → |
| 27 | Did You Ever ThinkR. Kelly | 54 | Chart history → |
| 28 | Fly AwayLenny Kravitz | 25 | Chart history → |
| 29 | Write This DownGeorge Strait | 29 | Chart history → |
| 30 | If You (Lovin' Me)Silk | 26 | Chart history → |
| 31 | Two TeardropsSteve Wariner | 30 | Chart history → |
| 32 | What's It Gonna Be?!Busta Rhymes Featuring Janet | 24 | Chart history → |
| 33 | Angel Of MineMonica | 28 | Chart history → |
| 34 | All I Have To GiveBackstreet Boys | 35 | Chart history → |
| 35 | Holla HollaJa Rule | 40 | Chart history → |
| 36 | SometimesBritney Spears | 48 | Chart history → |
| 37 | Back 2 Goodmatchbox 20 | 33 | Chart history → |
| 38 | God Must Have Spent A Little More Time On YouAlabama Featuring 'N Sync | 49 | Chart history → |
| 39 | Man! I Feel Like A Woman!Shania Twain | 34 | Chart history → |
| 40 | You Won't Ever Be LonelyAndy Griggs | 31 | Chart history → |
| 41 | Praise YouFatboy Slim | 42 | Chart history → |
| 42 | I Will Remember You (Live)Sarah McLachlan | 53 | Chart history → |
| 43 | Whatever You SayMartina McBride | 44 | Chart history → |
| 44 | Can I Get A...Jay-Z Featuring Amil (Of Major Coinz) & Ja | 43 | Chart history → |
| 45 | With YouLila McCann | 45 | Chart history → |
| 46 | ...Baby One More TimeBritney Spears | 38 | Chart history → |
| 47 | My Favorite GirlDave Hollister | 39 | Chart history → |
| 48 | AngelSarah McLachlan | 36 | Chart history → |
| 49 | Tell Me It's RealK-Ci & JoJo | 58 | Chart history → |
| 50 | Save TonightEagle-Eye Cherry | 47 | Chart history → |
| 51 | Anyone ElseCollin Raye | 37 | Chart history → |
| 52 | Tonight The Heartache's On MeDixie Chicks | 59 | Chart history → |
| 53 | We Like To Party!Vengaboys | 51 | Chart history → |
| 54 | AmazedLonestar | 81 | Chart history → |
| 55 | Last KissPearl Jam | 64 | Chart history → |
| 56 | Better Days (And The Bottom Drops Out)Citizen King | 72 | Chart history → |
| 57 | Strong EnoughCher | 57 | Chart history → |
| 58 | A Night To RememberJoe Diffie | 66 | Chart history → |
| 59 | How Forever FeelsKenny Chesney | 52 | Chart history → |
| 60 | YouJesse Powell | 41 | Chart history → |
| 61 | Lesson In Leavin'Jo Dee Messina | 75 | Chart history → |
| 62 | Wish You Were HereMark Wills | 50 | Chart history → |
| 63 | Blue MondayOrgy | 65 | Chart history → |
| 64 | One Honest HeartReba | 67 | Chart history → |
| 65 | Sitting HomeTotal | 55 | Chart history → |
| 66 | My Own Worst EnemyLit | 61 | Chart history → |
| 67 | What'd You Come Here For?Trina & Tamara | 68 | Chart history → |
| 68 | I Still BelieveMariah Carey | 63 | Chart history → |
| 69 | Anything But DownSheryl Crow | 56 | Chart history → |
| 70 | No PigeonsSporty Thievz Featuring Mr. Woods | 60 | Chart history → |
| 71 | Single White FemaleChely Wright | 86 | Chart history → |
| 72 | It Ain't My Fault 1 & 2Silkk The Shocker Featuring Mystikal | 73 | Chart history → |
| 73 | Little Good-ByesSHeDAISY | 78 | Chart history → |
| 74 | Scar TissueRed Hot Chili Peppers | 89 | Chart history → |
| 75 | Hey Leonardo (She Likes Me For Me)Blessid Union Of Souls | — | Chart history → |
| 76 | Hello L.O.V.E.John Michael Montgomery | 87 | Chart history → |
| 77 | NannTrick Daddy Featuring Trina | 62 | Chart history → |
| 78 | Beautiful StrangerMadonna | — | Chart history → |
| 79 | MillenniumRobbie Williams | 80 | Chart history → |
| 80 | She's Always RightClay Walker | — | Chart history → |
| 81 | Stranger In My MirrorRandy Travis | 85 | Chart history → |
| 82 | All Night LongFaith Evans Featuring Puff Daddy | 84 | Chart history → |
| 83 | I'll Think Of A Reason LaterLee Ann Womack | 82 | Chart history → |
| 84 | Why Don't You Get A Job?The Offspring | 94 | Chart history → |
| 85 | I Drive Myself Crazy'N Sync | 83 | Chart history → |
| 86 | OneCreed | 91 | Chart history → |
| 87 | My First Night With YouMya | 76 | Chart history → |
| 88 | What's So DifferentGinuwine | 77 | Chart history → |
| 89 | It's Over NowDeborah Cox | 70 | Chart history → |
| 90 | SpecialGarbage | 74 | Chart history → |
| 91 | Hands Of A Working ManTy Herndon | 79 | Chart history → |
| 92 | LifeK-Ci & JoJo | 88 | Chart history → |
| 93 | Georgy PorgyEric Benet Featuring Faith Evans | 71 | Chart history → |
| 94 | Maybe Not TonightSammy Kershaw & Lorrie Morgan | 90 | Chart history → |
| 95 | The Cup Of Life (The Official Song Of The World Cup, France '98)Ricky Martin | — | Chart history → |
| 96 | Players HolidayT.W.D.Y. Featuring Too Short & Mac Mall | 100 | Chart history → |
| 97 | HeavyCollective Soul | 98 | Chart history → |
| 98 | She's A BitchMissy "Misdemeanor" Elliott | 99 | Chart history → |
| 99 | Hate Me NowNas Featuring Puff Daddy | 95 | Chart history → |
| 100 | Ordinary LifeChad Brock | 96 | Chart history → |