US Top 40 Singles For The Week Ending October 2, 1999

POSTED:Nov 27, 2025 1:51 AM

These are all the US Top 40 Singles for the Week Ending October 2, 1999

US Top 40 Singles Week Ending OCTOBER 2, 1999

#1 UNPRETTY By TLC

US Top 40 Singles – OCTOBER 2, 1999

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

1 1 UNPRETTY –•– TLC – 15 (1)
2 2 SHE’S ALL I EVER HAD –•– Ricky Martin – 9 (2)
3 7 SMOOTH –•– Santana Featuring Rob Thomas – 10 (3)
4 6 MAMBO NO. 5 (A LITTLE BIT OF …) –•– Lou Bega – 6 (4)
5 3 BAILAMOS –•– Enrique Iglesias – 13 (1)
6 4 GENIE IN A BOTTLE –•– Christina Aguilera – 14 (1)
7 9 SOMEDAY –•– Sugar Ray – 14 (7)
8 8 ALL STAR –•– Smash Mouth – 20 (4)
9 12 SCAR TISSUE –•– Red Hot Chili Peppers – 18 (9)
10 56 I NEED TO KNOW –•– Marc Anthony – 4 (10)

11 16 MY LOVE IS YOUR LOVE –•– Whitney Houston – 5 (11)
12 10 WHERE MY GIRLS AT? –•– 702 – 23 (4)
13 13 I DO (CHERISH YOU) –•– 98 Degrees – 9 (13)
14 5 SUMMER GIRLS –•– LFO – 12 (3)
15 62 WE CAN’T BE FRIENDS –•– Deborah Cox & R.L. – 4 (15)
16 23 HEARTBREAKER –•– Mariah Carey Featuring Jay-Z – 5 (16)
17 14 I WANT IT THAT WAY –•– Backstreet Boys – 24 (6)
18 18 BLACK BALLOON –•– Goo Goo Dolls – 13 (18)
19 11 LOST IN YOU –•– Garth Brooks as Chris Gaines – 4 (5)
20 15 SHE’S SO HIGH –•– Tal Bachman – 16 (14)

21 21 STEAL MY SUNSHINE –•– Len – 8 (21)
22 22 SPEND MY LIFE WITH YOU –•– Eric Benet Featuring Tamia – 14 (21)
23 17 BILLS, BILLS, BILLS –•– Destiny’s Child – 16 (1)
24 20 SO ANXIOUS –•– Ginuwine – 12 (16)
25 25 BACK THAT THANG UP –•– Juvenile Featuring Manny Fresh & Lil’ Wayne – 13 (25)
26 24 IF YOU HAD MY LOVE –•– Jennifer Lopez – 21 (1)
27 29 BACK AT ONE –•– Brian McKnight – 6 (27)
28 28 SOMETHING LIKE THAT –•– Tim McGraw – 8 (28)
29 19 LAST KISS –•– Pearl Jam – 19 (2)
30 26 NEVER GONNA LET YOU GO –•– Faith Evans – 13 (17)

31 32 VIVRANT THING –•– Q-Tip – 12 (31)
32 27 OUT OF MY HEAD –•– Fastball – 14 (20)
33 50 I WANT IT ALL –•– Warren G Featuring Mack 10 – 3 (33)
34 48 (YOU DRIVE ME) CRAZY –•– Britney Spears – 3 (34)
35 41 I LOVE YOU –•– Martina McBride – 6 (35)
36 30 TELL ME IT’S REAL –•– K-Ci & JoJo – 19 (2)
37 40 GET GONE –•– Ideal – 7 (37)
38 45 THERE SHE GOES –•– Sixpence None The Richer – 4 (38)
39 44 READY TO RUN –•– Dixie Chicks – 11 (39)
40 35 AMAZED –•– Lonestar – 18 (24)

THIS WEEK’S DROPS – OCTOBER 2, 1999

42 34 YOU HAD ME FROM HELLO –•– Kenny Chesney – 13 (34)
43 38 JIGGA MY NIGGA –•– Jay-Z – 15 (28)
45 39 LITTLE MAN –•– Alan Jackson – 13 (39)
46 31 WHAT YA WANT –•– Eve & Nokio – 14 (29)
49 36 I WILL REMEMBER YOU (LIVE) –•– Sarah McLachlan – 20 (14)
50 33 IT’S ALL ABOUT YOU (NOT ABOUT ME) –•– Tracie Spencer – 8 (18)

POWER PLAYS – OCTOBER 2, 1999

41 52 MUSIC OF MY HEART –•– ‘N Sync & Gloria Estefan – 5 (41)
47 60 LARGER THAN LIFE –•– Backstreet Boys – 3 (47)

NEW THIS WEEK – OCTOBER 2, 1999

81 — HOME TO YOU –•– John Michael Montgomery – 1 (81)
82 — I’LL GO CRAZY –•– Andy Griggs – 1 (82)
84 — THE CHEMICALS BETWEEN US –•– Bush – 1 (84)
91 — 15 MINUTES –•– Marc Nelson – 1 (91)