THIS
YEAR | LAST
YEAR | ARTIST | TITLE | 1999
PEAK |
| 99 | -- | TRAIN | Meet Virginia | 30 |
| 98 | -- | BARENAKED LADIES | It's All Been Done | 27 |
| 97 | -- | JAY-Z | Can I Get A... | 24 |
| 96 | -- | DESTINY'S CHILD | Bills, Bills, Bills | 25 |
| 95 | -- | MEJA | All 'Bout the Money | 31 |
| 94 | -- | ORGY | Stitches | 28 |
| 93 | 8 | THE BLENDERS | (I'm in Love With the) McDonalds Girl | 17 |
| 92 | -- | THE BOOMTANG BOYS | Pictures | 21 |
| 91 | 1 | BEN FOLDS FIVE | Brick | 24 |
| 90 | 2 | BLACK LAB | Time Ago | 22 |
| 89 | -- | HOLE | Malibu | 24 |
| 88 | -- | EMINEM | My Name Is | 23 |
| 87 | -- | DAVE MATTHEWS BAND | Crush | 23 |
| 86 | 70 | BRITNEY SPEARS | ...Baby One More Time | 8 |
| 85 | -- | IDINA MENZEL | Minuet | 23 |
| 84 | -- | FATBOY SLIM | Praise You | 17 |
| 83 | -- | FASTBALL | Out of My Head | 22 |
| 82 | -- | GARTH BROOKS IN THE LIFE OF CHRIS GAINES | Right Now | 13 |
| 81 | -- | JUVENILE | Back That Thang Up | 7 |
| 80 | 22 | GREEN DAY | Good Riddance (Time of Your Life) | 16 |
| 79 | -- | BLESSID UNION OF SOULS | Standing at the Edge of the Earth | 17 |
| 78 | -- | CELINE DION | That's the Way It Is | 9 |
| 77 | -- | TEXAS | In Our Lifetime | 26 |
| 76 | -- | 2PAC | Changes | 20 |
| 75 | -- | THE CORRS | So Young | 19 |
| 74 | 52 | DUNCAN SHEIK | Bite Your Tongue | 13 |
| 73 | 4 | TORI AMOS | Spark | 24 |
| 72 | -- | BABEL FISH | Mania | 18 |
| 71 | -- | CHER | All or Nothing | 18 |
| 70 | 74 | MADONNA | The Power of Goodbye | 15 |
| 69 | -- | LIMP BIZKIT | Nookie | 11 |
| 68 | -- | SPLENDER | Yeah, Whatever | 11 |
| 67 | -- | OLEANDER | I Walk Alone | 2 |
| 66 | 48 | BILLIE MYERS | Tell Me | 10 |
| 65 | -- | BREE SHARP | David Duchovny | 13 |
| 64 | -- | 702 | Where My Girls At? | 21 |
| 63 | -- | FAITHLESS | God is a DJ | 21 |
| 62 | -- | DONNA SUMMER | I Will Go With You | 15 |
| 61 | -- | TOMMY HENRIKSEN | I See the Sun | 16 |
| 60 | -- | RUFUS WAINWRIGHT | Instant Pleasure | 11 |
| 59 | -- | ROBBIE WILLIAMS | Angels | 8 |
| 58 | -- | MADONNA | Beautiful Stranger | 11 |
| 57 | -- | THE BLENDERS | Can't Get Over You | 14 |
| 56 | -- | GARBAGE | When I Grow Up | 21 |
| 55 | -- | MOUSSE T vs. HOT 'N' JUICY | Horny | 4 |
| 54 | 15 | BARENAKED LADIES | One Week | 4 |
| 53 | 37 | THIRD EYE BLIND | Jumper | 2 |
| 52 | -- | BRITNEY SPEARS | (You Drive Me) Crazy | 6 |
| 51 | -- | EVERCLEAR | Father of Mine | 12 |
| 50 | -- | BLACKSTREET & MYA f/ MASE & BLINKY BLINK | Take Me There | 14 |
| 49 | -- | JENNIFER LOPEZ | If You Had My Love | 9 |
| 48 | -- | JENNIFER LOPEZ | Waiting For Tonight | 3 |
| 47 | 51 | MONICA | The First Night | 5 |
| 46 | -- | WHITNEY HOUSTON | It's Not Right But It's Okay | 11 |
| 45 | -- | ALANIS MORISSETTE | So Pure | 11 |
| 44 | -- | LIT | My Own Worst Enemy | 15 |
| 43 | 43 | LENNY KRAVITZ | Fly Away | 8 |
| 42 | 11 | JOHN MELLENCAMP | Your Life is Now | 3 |
| 41 | -- | TLC | No Scrubs | 10 |
| 40 | 20 | EAGLE-EYE CHERRY | Save Tonight | 2 |
| 39 | -- | MARC ANTHONY | I Need to Know | 7 |
| 38 | -- | JANA | Ooh Baby Baby | 6 |
| 37 | -- | STARS ON 54 | If You Could Read My Mind | 11 |
| 36 | -- | VENGABOYS | We Like to Party! | 10 |
| 35 | -- | SHERYL CROW | Sweet Child O' Mine | 4 |
| 34 | -- | SKY | Love Song | 8 |
| 33 | -- | ROBBIE WILLIAMS | Millennium | 12 |
| 32 | -- | WHITNEY HOUSTON f/ FAITH EVANS & KELLY PRICE | Heartbreak Hotel | 3 |
| 31 | -- | CAKE | Never There | 11 |
| 30 | -- | SMASH MOUTH | All Star | 1 (1 WEEK) |
| 29 | -- | JAMIROQUAI | Canned Heat | 5 |
| 28 | -- | AMBER | Sexual (Li Da Di) | 13 |
| 27 | -- | LEN | Steal My Sunshine | 1 (4 WEEKS) |
| 26 | -- | 98 DEGREES | The Hardest Thing | 2 |
| 25 | -- | GARBAGE | Special | 8 |
| 24 | -- | KHALEEL | No Mercy | 11 |
| 23 | 96 | WILL SMITH | Miami | 6 |
| 22 | -- | LOU BEGA | Mambo No. 5 | 1 (1 WEEK) |
| 21 | -- | MONIFAH | Touch It | 2 |
| 20 | -- | TLC | Unpretty | 4 |
| 19 | -- | FUEL | Shimmer | 4 |
| 18 | -- | BILLIE | She Wants You | 3 |
| 17 | -- | GOO GOO DOLLS | Black Balloon | 7 |
| 16 | -- | PEARL JAM | Last Kiss | 1 (8 WEEKS) |
| 15 | 12 | INOJ | Time After Time | 6 |
| 14 | -- | CHRISTINA AGUILERA | Genie in a Bottle | 2 |
| 13 | 50 | SHAWN MULLINS | Lullaby | 1 (5 WEEKS) |
| 12 | 75 | P.M. DAWN | I Had No Right | 2 |
| 11 | -- | BLONDIE | Maria | 3 |
| 10 | -- | CHER | Believe | 2 |
| 9 | -- | CITIZEN KING | Better Days | 1 (1 WEEK) |
| 8 | -- | THE NEW RADICALS | Someday We'll Know | 1 (3 WEEKS) |
| 7 | -- | CREED | One | 1 (2 WEEKS) |
| 6 | -- | ORGY | Blue Monday | 1 (5 WEEKS) |
| 5 | -- | EVERLAST | What It's Like | 2 |
| 4 | -- | MATCHBOX 20 | Back 2 Good | 3 |
| 3 | -- | FLEMING AND JOHN | Ugly Girl | 1 (6 WEEKS) |
| 2 | -- | THE TAMPERER f/ MAYA | If You Buy This [Record (Your Life Will Be Better)] | 1 (4 WEEKS) |
| 1 | -- | THE NEW RADICALS | You Get What You Give | 1 (12 WEEKS) |
