January 12 - Britney Spears releases her debut album, ...Baby One More Time. The album hits number one on the charts.
April 20 - Columbine High School massacre takes place in Jefferson County, Colorado. It sparks a widespread moral panic that ultimately tries to place the blame on violent media.
August 24 - Christina Aguilera releases her self titled debut album. The album and first single, "Genie In A Bottle" both went to number one on the charts
December 29 - Former Beatle George Harrison is stabbed several times in the chest by an unknown assailant, who had broke into Harrison's home. Harrison's wife wrestled the knife out the assailant's hand before the police arrived. The man apparently believed that Harrison was the devil.

1. All Star - Smash Mouth
2. Man! I Feel Like A Woman - Shania Twain
3. Mambo No. 5 - Lou Bega
4. I Need To Know - Marc Anthony
5. Smooth - Santana (with Rob Thomas)
6. Livin La Vita Loca - Ricky Martin
7. Canned Heat - Jamiroquai (Napolean Dynamite dance song)
8. Believe - Cher
9. Summergirls - LFO
10. My Name Is... - Eminem
11. Crush - Dave Matthews Band
12. Last Kiss - Pearl Jam
13. What's My Age Again? - Blink 182
14. Changes - 2 Pac
15. We Like To Party! - Venga Boys
16. Cup Of Life - Ricky Martin
17. (You Drive Me) Crazy - Britney Spears
18. All The Small Things - Blink 182
19. I Will Remember You - Sarah McLachlan
20. Someday - Sugar Ray
21. Genie In a Bottle - Christina Aguilera
22. Why Don't You Get A Job? - The Offspring
23. Miami - Will Smith
24. Have You Ever? - Brandy
25. Shake Your Bon Bon - Ricky Martin
26. Boom, Boom, Boom, Boom! - Venga Boys
27. That Don't Impress Me Much - Shania Twain
28. Back At One - Brian McKnight
29. ...Baby One More Time - Britney Spears
30. Every Morning - Sugar Ray
31. Slide - Goo Goo Dolls
32. Blue - Eiffel 65
33. No Scrubs - TLC
34. Angel - Sarah McLachlan
35. My Own Worst Enemy - Lit
36. Back That Azz Up - Juvenile
37. Larger Than Life - Backstreet Boys
38. Pretty Fly For A White Guy - the Offspring
39. Out of My Head - Fastball
40. I Knew I Loved You - Savage Garden
41. Bills Bills Bills - Destiny's Child
42. I Do (Cherish You) - 98 Degrees (98°)
43. She's All I Ever Had - Ricky Martin
44. Cowboy - Kid Rock
45. Bailamos - Enrique Iglesias
46. Got Your Money - Dirty Old Bastard
47. Unpretty - TLC
48. Back 2 Good - Matchbox 20
49. Hard Knock Life - Jay-Z
50. everybody's free (To Wear Sunscreen) - Baz Luhrmann
51. She Thinks My Tractor's Sexy - Kenny Chesney
52. When You Believe - Mariah Carey & Whitney Houston
53. Can I Get A... - Jay Z Featuring Amil & JA Rule
54. I Could Not Ask For More - Edwin McCain
55. I Wanna Love You Forever - Jessica Simpson
56. Steal My Sunshine - Len
57. You'll Be In My Heart - Phil Collins (Tarzan soundtrack)
58. Never There - Cake
59. Anywhere - 112
60 Come On Over - Shania Twain
61. Girl on TV - LFO
62. Vivrant Thing - Nas
63. If You had My Love - Jennifer Lopez
64. Holla Holla - Ja Rule
65. Angel of Mine - Monica
66. Strong Enough - Cher
67. Nookie - Limp Bizkit
68. It's All Been Done - Barenaked Ladies
69. Jumper - Third Eye Blind
70. Special - Garbage
71. (God Must Have Spent) A Little More Time On You - *NSYNC
72. American Woman - Lennie Kravitz
73. C'est La Vie - B*Witched
74. Unsent - Alanis Morissette
75. Fly Away - Lenny Kravitz

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December 5 - January 15: I'm Your Angel - R. Kelly & Céline Dion
January 16 - January 29: Have You Ever - Brandy
January 30 - February 7: ...Baby One More Time - Britney Spears
February 13 - March 12: Angel Of Mine - Monica
March 13 - April 9: Believe - Cher
April 10 - May 7: No Scrubs - TLC
May 8 - June 4: Livin' La Vida Loca - Ricky Martin
June 5 - July 16: If You Had My Love - Jennifer Lopez
July 17 - July 23: Bills, Bills, Bills - Destiny's Child
July 24 - July 30: Wild Wild West - Will Smith featuring Dru Hill and Kool Moe Dee
July 31 - September 3: Genie In A Bottle - Christina Aguilera
September 4 - September 17: Bailamos - Enrique Iglesias
September 18 - October 8: Unpretty - TLC
October 9 - October 22: Heartbreaker - Mariah Carey featuring Jay-Z
October 23, 1999- January 14, 2000: Smooth - Santana featuring Rob Thomas