| Cover | | Date  | Title • Artist  Album | Points  | Charts Peaks | Comment |
|---|
![Livin' la Vida Loca [article] Livin' la Vida Loca [article]](./wp/cache/img/JMGSong_35021.jpg) | 1. | 04/1999 | | 361
 | US ✫1 UK ✫1 US dance 5 | written by Ricky Martin, Desmond Child & Draco Rosa (as Robi Rosa) |
![If You Had My Love [article] If You Had My Love [article]](./wp/cache/img/JMGSong_21248.jpg) | 2. | 05/1999 | | 346
 | US ✫1 UK 4 US dance 5 US R&B 6 | [Work 79163] written by LaShawn Daniels, Fred Jerkins III, Rodney Jerkins & Cory Rooney |
![Say My Name [article] Say My Name [article]](./wp/cache/img/JMGSong_11678.jpg) | 3. | 12/1999 | | 321
 | US ✫1 UK 3 US dance 39 US R&B ✫1 | |
![Heartbreaker [article] Heartbreaker [article]](./wp/cache/img/JMGSong_27441.jpg) | 4. | 09/1999 | | 308
 | US ✫1 UK 5 US dance 2 US R&B ✫1 | featuring Jay-Z written by Mariah Carey, Sean Carter, Shirley Elliston, Lincoln Chase, Michael Walden & Jeffrey Cohen |
![My Love Is Your Love [article] My Love Is Your Love [article]](./wp/cache/img/JMGSong_48770.jpg) | 5. | 07/1999 | | 299
 | US 4 UK 2 US dance ✫1 US R&B 2 | written by Jerry Duplessis & Wyclef Jean |
![Bailamos [article] Bailamos [article]](./wp/cache/img/JMGSong_14612.jpg) | 6. | 07/1999 | | 298
 | US ✫1 UK 4 US dance ✫1 | |
![What a Girl Wants [article] What a Girl Wants [article]](./wp/cache/img/JMGSong_8797.jpg) | 7. | 11/1999 | | 295
 | US ✫1 UK 3 US dance 18 | |
![Blue (Da Ba Dee) [article] Blue (Da Ba Dee) [article]](./wp/cache/img/JMGSong_13822.jpg) | 8. | 09/1999 | | 287
 | US 6 UK ✫1 US dance 6 | |
![Bills, Bills, Bills [article] Bills, Bills, Bills [article]](./wp/cache/img/JMGSong_11676.jpg) | 9. | 06/1999 | | 284
 | US ✫1 UK 6 US dance 13 US R&B ✫1 | |
![It's Not Right but It's Okay [article] It's Not Right but It's Okay [article]](./wp/cache/img/JMGSong_48769.jpg) | 10. | 01/1999 | | 279
 | US 4 UK 3 US dance ✫1 US R&B 7 | written by LaShawn Daniels, Toni Estes, Rodney Jerkins, Fred Jerkins III & Isaac Phillips |
![I Still Believe [article] I Still Believe [article]](./wp/cache/img/JMGSong_27440.jpg) | 11. | 02/1999 | | 228
 | US 4 UK 16 US AC 8 US dance ✫1 US R&B 3 | written by Antonina Armato & Giuseppe Cantarelli |
![Waiting for Tonight [article] Waiting for Tonight [article]](./wp/cache/img/JMGSong_21249.jpg) | 12. | 10/1999 | | 209
 | US 8 UK 5 US dance ✫1 | [Work 79292] written by Maria Christensen, Michael Garvin & Phil Temple |
![Beautiful Stranger [article] Beautiful Stranger [article]](./wp/cache/img/JMGSong_27127.jpg) | 13. | 06/1999 | | 197
 | US 19 UK 2 US AC 23 US dance ✫1 | Not commercially released in the U.S. [album cut] written by Madonna & William Orbit |
![Dímelo (I Need to Know) [article] Dímelo (I Need to Know) [article]](./wp/cache/img/JMGSong_27337.jpg) | 14. | 09/1999 | | 182
 | US 3 UK 28 US dance 12 | [Latin Grammy Award for Song of the Year 2000] written by Marc Anthony & Cory Rooney |
![Better Off Alone [article] Better Off Alone [article]](./wp/cache/img/JMGSong_1745.jpg) | 15. | 07/1999 | | 175
 | US 27 UK 2 US dance 3 | as DJ Jürgen presents Alice DeeJay |
![Give It to You [article] Give It to You [article]](./wp/cache/img/JMGSong_23349.jpg) | 16. | 04/1999 | | 169
 | US 10 UK 5 US dance 35 | [Interscope 97048] written by Jordan Knight, Jimmy Jam (as James Harris III), Terry Lewis & Robin Thicke |
![King of My Castle [article] King of My Castle [article]](./wp/cache/img/JMGSong_48326.jpg) | 17. | 11/1999 | | 161
 | UK ✫1 US dance ✫1 | |
![We Like to Party! (Vengabus) [article] We Like to Party! (Vengabus) [article]](./wp/cache/img/JMGSong_48033.jpg) | 18. | 02/1999 | | 161
 | US 26 UK 3 US dance 5 | |
![9pm (Till I Come) [article] 9pm (Till I Come) [article]](./wp/cache/img/JMGSong_3143.jpg) | 19. | 05/1999 | | 158
 | UK ✫1 US dance 7 | |
![You Don't Know Me [article] You Don't Know Me [article]](./wp/cache/img/JMGSong_2921.jpg) | 20. | 02/1999 | | 157
 | UK ✫1 US dance 2 | featuring Duane Harden |
![Maria [article] Maria [article]](./wp/cache/img/JMGSong_5589.jpg) | 21. | 02/1999 | | 155
 | US 82 UK ✫1 US dance 9 | written by Jimmy Destri |
![Boom, Boom, Boom, Boom! [article] Boom, Boom, Boom, Boom! [article]](./wp/cache/img/JMGSong_48034.jpg) | 22. | 06/1999 | | 155
 | US 84 UK ✫1 US dance 13 | |
![Take a Picture [article] Take a Picture [article]](./wp/cache/img/JMGSong_15553.jpg) | 23. | 10/1999 | | 153
 | US 12 UK 25 US dance ✫1 US rock 4 US alt. 3 | |
![Mi Chico Latino [article] Mi Chico Latino [article]](./wp/cache/img/JMGSong_17553.jpg) | 24. | 08/1999 | | 145
 | UK ✫1 US dance 19 | written by Geri Halliwell, Andy Watkins & Paul Wilson |
| 25. | 02/1999 | | 137
 | US 9 UK 23 US dance 4 US R&B 3 | featuring Puff Daddy [Bad Boy 79203] written by Diddy (as Sean Combs), S. Crawford, Faith Evans, T. Gaither, R. Lawrence, B.J. Reed, T. Russaw & G. Underwo |
![Look at Me [article] Look at Me [article]](./wp/cache/img/JMGSong_17552.jpg) | 26. | 05/1999 | | 130
 | UK 2 US dance 12 | written by Geri Halliwell, Andy Watkins & Paul Wilson |
| 27. | 09/1999 | | 129
 | UK 3 US dance ✫1 | written by Bob Marley |
![Strong Enough [article] Strong Enough [article]](./wp/cache/img/JMGSong_8500.jpg) | 28. | 03/1999 | | 122
 | US 57 UK 5 US dance ✫1 | |
![Rendez-Vu [article] Rendez-Vu [article]](./wp/cache/img/JMGSong_3966.jpg) | 29. | 08/1999 | | 120
 | UK 4 US dance ✫1 | |
![Canned Heat [article] Canned Heat [article]](./wp/cache/img/JMGSong_20853.jpg) | 30. | 06/1999 | | 120
 | UK 4 US dance ✫1 | |
![Chanté's Got a Man [article] Chanté's Got a Man [article]](./wp/cache/img/JMGSong_8218.jpg) | 31. | 05/1999 | | 119
 | US 10 US dance 34 US R&B 2 | |
![Red Alert [article] Red Alert [article]](./wp/cache/img/JMGSong_3965.jpg) | 32. | 05/1999 | | 111
 | UK 5 US dance ✫1 | |
| 33. | 09/1999 | | 109
 | UK 5 US dance ✫1 | |
| 34. | 12/1999 | | 109
 | UK 4 US dance 13 | |
| 35. | 12/1999 | | 105
 | UK 4 US dance 27 | |
![I Learned from the Best [article] I Learned from the Best [article]](./wp/cache/img/JMGSong_48771.jpg) | 36. | 12/1999 | | 104
 | US 27 UK 19 US dance ✫1 US R&B 13 | written by Diane Warren |
![Nothing Really Matters [article] Nothing Really Matters [article]](./wp/cache/img/JMGSong_27126.jpg) | 37. | 03/1999 | | 100
 | US 93 UK 7 US dance ✫1 | [Maverick 17102] written by Madonna & Patrick Leonard |
| 38. | 12/1999 | | 94
 | UK 5 US dance 26 | |
| 39. | 02/1999 | | 87
 | UK 9 US dance 4 US alt. 23 | |
| 40. | 01/1999 | | 86
 | UK 7 US dance 8 | |