US Top 40 Singles For The Week Ending October 16, 1999

POSTED:Nov 27, 2025 1:55 AM

These are all the US Top 40 Singles for the Week Ending October 16, 1999

US Top 40 Singles Week Ending OCTOBER 16, 1999

#1 HEARTBREAKER By Mariah Carey Featuring Jay-Z

US Top 40 Singles – OCTOBER 16, 1999

TW LW TITLE Artist – Weeks on Chart (Peak Position)

1 1 HEARTBREAKER –•– Mariah Carey Featuring Jay-Z – 7 (1)
2 41 MUSIC OF MY HEART –•– ‘N Sync & Gloria Estefan – 7 (2)
3 2 SMOOTH –•– Santana Featuring Rob Thomas – 12 (2)
4 3 UNPRETTY –•– TLC – 17 (1)
5 4 MAMBO NO. 5 (A LITTLE BIT OF …) –•– Lou Bega – 8 (4)
6 5 SHE’S ALL I EVER HAD –•– Ricky Martin – 11 (2)
7 6 GENIE IN A BOTTLE –•– Christina Aguilera – 16 (1)
8 9 MY LOVE IS YOUR LOVE –•– Whitney Houston – 7 (8)
9 7 SOMEDAY –•– Sugar Ray – 16 (7)
10 8 I NEED TO KNOW –•– Marc Anthony – 6 (8)

11 10 SCAR TISSUE –•– Red Hot Chili Peppers – 20 (9)
12 17 IF I COULD TURN BACK THE HANDS OF TIME –•– R. Kelly – 8 (12)
13 13 WE CAN’T BE FRIENDS –•– Deborah Cox & R.L. – 6 (13)
14 14 WHERE MY GIRLS AT? –•– 702 – 25 (4)
15 12 ALL STAR –•– Smash Mouth – 22 (4)
16 11 BAILAMOS –•– Enrique Iglesias – 15 (1)
17 18 STEAL MY SUNSHINE –•– Len – 10 (17)
18 15 I DO (CHERISH YOU) –•– 98 Degrees – 11 (13)
19 16 BLACK BALLOON –•– Goo Goo Dolls – 15 (16)
20 20 SHE’S SO HIGH –•– Tal Bachman – 18 (14)

21 24 BACK AT ONE –•– Brian McKnight – 8 (21)
22 22 BACK THAT THANG UP –•– Juvenile Featuring Manny Fresh & Lil’ Wayne – 15 (22)
23 21 I WANT IT THAT WAY –•– Backstreet Boys – 26 (6)
24 29 (YOU DRIVE ME) CRAZY –•– Britney Spears – 5 (24)
25 23 LOST IN YOU –•– Garth Brooks as Chris Gaines – 6 (5)
26 25 SPEND MY LIFE WITH YOU –•– Eric Benet Featuring Tamia – 16 (21)
27 31 VIVRANT THING –•– Q-Tip – 14 (27)
28 30 I WANT IT ALL –•– Warren G Featuring Mack 10 – 5 (28)
29 35 I LOVE YOU –•– Martina McBride – 8 (29)
30 34 LARGER THAN LIFE –•– Backstreet Boys – 5 (30)

31 28 SOMETHING LIKE THAT –•– Tim McGraw – 10 (28)
32 26 SO ANXIOUS –•– Ginuwine – 14 (16)
33 37 GET GONE –•– Ideal – 9 (33)
34 40 MAN! I FEEL LIKE A WOMAN! –•– Shania Twain – 23 (34)
35 27 BILLS, BILLS, BILLS –•– Destiny’s Child – 18 (1)
36 44 GOTTA MAN –•– Eve – 5 (36)
37 19 SUMMER GIRLS –•– LFO – 14 (3)
38 38 THERE SHE GOES –•– Sixpence None The Richer – 6 (38)
39 39 READY TO RUN –•– Dixie Chicks – 13 (39)
40 46 BUG A BOO –•– Destiny’s Child – 4 (40)

THIS WEEK’S DROPS – OCTOBER 16, 1999

41 32 IF YOU HAD MY LOVE –•– Jennifer Lopez – 23 (1)
42 33 OUT OF MY HEAD –•– Fastball – 16 (20)
47 36 NEVER GONNA LET YOU GO –•– Faith Evans – 15 (17)

POWER PLAYS – OCTOBER 16, 1999

43 63 SATISFY YOU –•– Puff Daddy Featuring R. Kelly – 4 (43)
44 48 U KNOW WHAT’S UP –•– Donell Jones – 4 (44)
45 45 BLING BLING –•– B.G. Featuring Baby, Turk, Mannie Fresh & Juvenile – 5 (45)
48 54 WHAT DO YOU SAY TO THAT –•– George Strait – 7 (48)
49 58 I’M ALREADY TAKEN –•– Steve Wariner – 6 (49)

NEW THIS WEEK – OCTOBER 16, 1999

56 — WAITING FOR TONIGHT –•– Jennifer Lopez – 1 (56)
69 — I WANNA LOVE YOU FOREVER –•– Jessica Simpson – 1 (69)
71 — BIG DEAL –•– LeAnn Rimes – 1 (71)
75 — WHEN I SAID I DO –•– Clint Black – 1 (75)
80 — LEARN TO FLY –•– Foo Fighters – 1 (80)
82 — MISSING YOU –•– Brooks & Dunn – 1 (82)
84 — THE DOLPHIN’S CRY –•– Live – 1 (84)
100 — STEAM –•– Ty Herndon – 1 (100)