US Top 40 Singles For The Week Ending October 23, 1999

POSTED:Nov 27, 2025 1:58 AM

These are all the US Top 40 Singles for the Week Ending October 23, 1999

US Top 40 Singles Week Ending OCTOBER 23, 1999

#1 SMOOTH By Santana Featuring Rob Thomas

US Top 40 Singles – OCTOBER 23, 1999

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

1 3 SMOOTH –•– Santana Featuring Rob Thomas – 13 (1)
2 1 HEARTBREAKER –•– Mariah Carey Featuring Jay-Z – 8 (1)
3 2 MUSIC OF MY HEART –•– ‘N Sync & Gloria Estefan – 8 (2)
4 4 UNPRETTY –•– TLC – 18 (1)
5 5 MAMBO NO. 5 (A LITTLE BIT OF …) –•– Lou Bega – 9 (4)
6 43 SATISFY YOU –•– Puff Daddy Featuring R. Kelly – 5 (6)
7 8 MY LOVE IS YOUR LOVE –•– Whitney Houston – 8 (7)
8 13 WE CAN’T BE FRIENDS –•– Deborah Cox & R.L. – 7 (8)
9 10 I NEED TO KNOW –•– Marc Anthony – 7 (8)
10 11 SCAR TISSUE –•– Red Hot Chili Peppers – 21 (9)

11 9 SOMEDAY –•– Sugar Ray – 17 (7)
12 7 GENIE IN A BOTTLE –•– Christina Aguilera – 17 (1)
13 6 SHE’S ALL I EVER HAD –•– Ricky Martin – 12 (2)
14 12 IF I COULD TURN BACK THE HANDS OF TIME –•– R. Kelly – 9 (12)
15 14 WHERE MY GIRLS AT? –•– 702 – 26 (4)
16 17 STEAL MY SUNSHINE –•– Len – 11 (16)
17 18 I DO (CHERISH YOU) –•– 98 Degrees – 12 (13)
18 21 BACK AT ONE –•– Brian McKnight – 9 (18)
19 15 ALL STAR –•– Smash Mouth – 23 (4)
20 19 BLACK BALLOON –•– Goo Goo Dolls – 16 (16)

21 16 BAILAMOS –•– Enrique Iglesias – 16 (1)
22 22 BACK THAT THANG UP –•– Juvenile Featuring Manny Fresh & Lil’ Wayne – 16 (22)
23 24 (YOU DRIVE ME) CRAZY –•– Britney Spears – 6 (23)
24 20 SHE’S SO HIGH –•– Tal Bachman – 19 (14)
25 33 GET GONE –•– Ideal – 10 (25)
26 27 VIVRANT THING –•– Q-Tip – 15 (26)
27 26 SPEND MY LIFE WITH YOU –•– Eric Benet Featuring Tamia – 17 (21)
28 28 I WANT IT ALL –•– Warren G Featuring Mack 10 – 6 (28)
29 29 I LOVE YOU –•– Martina McBride – 9 (29)
30 23 I WANT IT THAT WAY –•– Backstreet Boys – 27 (6)

31 44 U KNOW WHAT’S UP –•– Donell Jones – 5 (31)
32 31 SOMETHING LIKE THAT –•– Tim McGraw – 11 (28)
33 34 MAN! I FEEL LIKE A WOMAN! –•– Shania Twain – 24 (33)
34 30 LARGER THAN LIFE –•– Backstreet Boys – 6 (30)
35 32 SO ANXIOUS –•– Ginuwine – 15 (16)
36 36 GOTTA MAN –•– Eve – 6 (36)
37 56 WAITING FOR TONIGHT –•– Jennifer Lopez – 2 (37)
38 38 THERE SHE GOES –•– Sixpence None The Richer – 7 (38)
39 40 BUG A BOO –•– Destiny’s Child – 5 (39)
40 69 I WANNA LOVE YOU FOREVER –•– Jessica Simpson – 2 (40)

THIS WEEK’S DROPS – OCTOBER 23, 1999

42 39 READY TO RUN –•– Dixie Chicks – 14 (39)
43 25 LOST IN YOU –•– Garth Brooks as Chris Gaines – 7 (5)
44 35 BILLS, BILLS, BILLS –•– Destiny’s Child – 19 (1)
61 37 SUMMER GIRLS –•– LFO – 15 (3)

POWER PLAYS – OCTOBER 23, 1999

41 45 BLING BLING –•– B.G. Featuring Baby, Turk, Mannie Fresh & Juvenile – 6 (41)
47 49 I’M ALREADY TAKEN –•– Steve Wariner – 7 (47)
48 48 WHAT DO YOU SAY TO THAT –•– George Strait – 8 (48)
49 65 CANDY –•– Marc Moore – 7 (49)

NEW THIS WEEK – OCTOBER 23, 1999

71 — I KNEW I LOVED YOU –•– Savage Garden – 1 (71)
73 — BRING IT ALL TO ME –•– Blaque – 1 (73)
74 — COME ON OVER –•– Shania Twain – 1 (74)
83 — HE DIDN’T HAVE TO BE –•– Brad Paisley – 1 (83)
85 — GOT YOUR MONEY –•– Ol’ Dirty Bastard Featuring Kelis – 1 (85)
89 — U DON’T KNOW ME (LIKE U USED TO) –•– Brandy – 1 (89)
92 — GET IT ON TONITE Montell –•– Jordan – 1 (92)
94 — GIVE YOU WHAT YOU WANT (FA SURE) –•– Chico DeBarge – 1 (94)
96 — THE GREATEST ROMANCE EVER SOLD –•– Prince – 1 (96)
100 — SIMON SAYS –•– Pharoahe Monch – 1 (100)