| Artist | Song | Date Debuted | Date Entered Club | Peak Pos. |
| 'N Sync | A Little More Time on You | January 6, 1999 | July 31, 1999 | 11 |
| 'N Sync | This I Promise You | October 7, 2000 | May 19, 2001 | 5 |
| 702 | Where My Girls At | May 8, 1999 | December 11, 1999** | 4 |
| Amber | Sexual (Li Da Di) | September 25, 1999 | April 22, 2000 | 27 |
| Anggun | Snow on the Sahara | October 17, 1998 | May 22, 1999** | 29 |
| Backstreet Boys | I Want it That Way | May 1, 1999 | December 4, 1999 | 1(6) |
| BBMak | Back Here | July 1, 2000 | February 3, 2001 | 5 |
| Toni Braxton | He Wasn't Man Enough for Me | March 25, 2000 | October 14, 2000 | 6 |
| Vanessa Carlton | A Thousand Miles | July 20, 2002 | February 8, 2003 | 2 |
| Phil Collins | You'll Be in My Heart | May 15, 1999 | December 18, 1999 | 24 |
| The Corrs | Breathless | October 14, 2000 | May 26, 2001 | 14 |
| Creed | With Arms Wide Open | September 30, 2000 | May 12, 2001 | 2 |
| Dido | Thank You | January 13, 2000 | August 11, 2001** | 1 |
| Celine Dion & R Kelly | I'm Your Angel | November 7, 1998 | June 4, 1999 | 2 |
| Celine Dion | That's The Way it Is | November 20, 1999 | June 17, 2000 | 3 |
| Celine Dion | To Love You More | July 7, 1998 | January 30, 1999 | 7 |
| Enya | Only Time | July 17, 2001 | March 5, 2002** | 6 |
| Gloria Estefan & 'N Sync | The Music of My Heart | September 11, 1999 | April 8, 2000 | 11 |
| Goo Goo Dolls | Iris | July 7, 1998 | January 30, 1999 | 2 |
| Goo Goo Dolls | Slide | November 19, 1998 | July 3, 1999 | 11 |
| Faith Hill | Breathe | February 12, 2000 | September 1, 2000 | 5 |
| Faith Hill | The Way You Love Me | September 30, 2000 | May 12, 2001 | 12 |
| Joe | I Wanna Know | January 15, 2000 | August 5, 2000** | 3 |
| Norah Jones | Don't Know Why | September 28, 2002 | April 19, 2003** | 21 |
| Alicia Keys | Fallin' | July 10, 1998 | February 26, 2002 | 1 |
| Lifehouse | Hanging By a Moment | April 7, 2001 | November 9, 2001 | 1x3 |
| Lonestar | Amazed | January 15, 2000 | August 5, 2000 | 5 |
| Matchbox 20 | If You're Gone | November 24, 2000 | June 15, 2001** | 1 |
| Matchbox 20 | Unwell | March 22, 2003 | October 18, 2003** | 1 |
| Sarah McLachlan | Angel | November 26, 1998 | July 24, 1999* | 3 |
| Edwin McCain | I'll Be | July 7, 1998 | January 30, 1999 | 11 |
| Brian McKnight | Back At One | September 4, 1999 | April 1, 2000** | 1(13) |
| Monica | Angel of Mine | December 4, 1998 | July 17, 1999 | 1(7) |
| Santana f/Michelle Branch | The Game of Love | September 14, 2002 | April 5, 2003 | 1 |
| Santana f/Rob Thomas | Smooth | September 4, 1999 | April 1, 2000*** | 2 |
| Savage Garden | I Knew I Loved You | November 13, 1999 | June 10, 2000 | 1(2) |
| Sixpence None the Richer | Kiss Me | March 6, 1999 | September 25, 1999 | 3 |
| Spice Girls | Goodbye | January 23, 1999 | August 14, 1999 | 33 |
| Shania Twain | That Don't Impress Me Much | April 24, 1999 | November 27, 1999 | 3 |
| Train | Drops of Jupiter | May 12, 2003 | December 8, 2001 | 1 |
| Uncle Kracker f/Dobie Gray | Drift Away | April 12, 2003 | November 8, 2003 | 7 |
| Uncle Kracker | Follow Me | April 7, 2001 | November 9, 2001 | 7 |
| Vertical Horizon | Everything You Want | February 5, 2000 | August 26, 2000** | 12 |
| Lee Ann Womack | I Hope You Dance | February 3, 2001 | September 1, 2001 | 10 |
