Below is a list from Billboard magazine’s Top ear-End Hot 100 songs for 1999. Chart © by Billboard, a part of MRC Media and Info, a division of MRC. All Rights Reserved. Learn more about Billboard here.

Table of Contents

Top 100 Songs of 1999

1Angel of Mine – Monica

2Heartbreak Hotel – Whitney Houston

3Believe – Cher

4…Baby One More Time – Britney Spears

5No Scrubs – TLC

6Kiss Me – Sixpence None The Richer

7Every Morning – Sugar Ray

8Genie In a Bottle – Christina Aguilera

9Nobody’s Supposed to Be Here – Deborah Cox

10Livin’ la Vida Loca – Ricky Martin

11Where My Girls At? – 702

12If You Had My Love – Jennifer Lopez

13Have You Ever – Brandy

14Slide – Goo Goo Dolls

15I Want It That Way – Backstreet Boys

16I’m Your Angel – R. Kelly and Celine Dion

17All Star – Smash Mouth

18Angel – Sarah McLachlan

19Smooth – Santana featuring Rob Thomas

20Unpretty – TLC

21Save Tonight – Eagle-Eye Cherry

22Bills, Bills, Bills – Destiny’s Child

23Last Kiss – Pearl Jam

24Bailamos – Enrique Iglesias

25What’s It Gonna Be?! – Busta Rhymes featuring Janet

26What It’s Like – Everlast

27Fly Away – Lenny Kravitz

28That Don’t Impress Me Much – Shania Twain

29Wild Wild West – Will Smith featuring Dru Hill and Kool Moe Dee

30Scar Tissue – Red Hot Chili Peppers

31Heartbreaker – Mariah Carey featuring Jay-Z

32I Still Believe – Mariah Carey

33The Hardest Thing – 98 Degrees

34Summer Girls – LFO

35Can I Get A… – Jay-Z featuring Amil (Of Major Coinz) and Ja Rule

36Jumper – Third Eye Blind

37Doo Wop (That Thing) – Lauryn Hill

38Mambo No. 5 (A Little Bit Of…) – Lou Bega

39Sweet Lady – Tyrese

40It’s Not Right But It’s Okay – Whitney Houston

41(God Must Have Spent) A Little More Time on You – ‘N Sync

42Lullaby – Shawn Mullins

43Anywhere – 112 featuring Lil’Z

44Tell Me It’s Real – K-Ci and JoJo

45Back 2 Good – Matchbox 20

46808 – Blaque

More 54 Top Songs of 1999

47. 47. Fortunate – Maxwell
    48. All I Have to Give – Backstreet Boys
    49. Someday – Sugar Ray
    50. Lately – Divine
    51.  She’s So High – Tal Bachman
    52.  Bella (She’s All I Ever Had) – Ricky Martin
    53.  Miami – Will Smith
    54.  Hands – Jewel
    55.  Who Dat – JT Money featuring Sole
    56.  Please Remember Me – Tim McGraw
    57.  From This Moment On – Shania Twain
    58.  Love Like This – Faith Evans
    59.  You – Jesse Powell
    60.  Trippin’ – Total featuring Missy Elliott
    61.  If You – Silk
    62.  Ex-Factor – Lauryn Hill
    63.  Give It to You – Jordan Knight
    64.  Black Balloon – Goo Goo Dolls
    65.  Spend My Life With You – Eric Benet featuring Tamia
    66.  These Are the Times – Dru Hill
    67.  I Don’t Want to Miss a Thing – Mark Chesnutt
    68.  I Do (Cherish You) – 98 Degrees
    69.  Because of You – 98 Degrees
    70.  I Will Remember You – Sarah McLachlan
    71.  Chante’s Got a Man – Chanté Moore
    72.  Happily Ever After – Case
    73.  My Love Is Your Love – Whitney Houston
    74.  All Night Long – Faith Evans featuring Puff Daddy
    75.  Back That Thang Up – Juvenile featuring Mannie Fresh and Lil’ Wayne
    76.  Almost Doesn’t Count – Brandy
    77.  Man! I Feel Like a Woman! – Shania Twain
    78.  Steal My Sunshine – Len
    79.  I Need to Know – Marc Anthony
    80.  So Anxious – Ginuwine
    81.  Faded Pictures – Case and Joe
    82.  Back at One – Brian McKnight
    83.  When a Woman’s Fed Up – R. Kelly
    84.  How Forever Feels – Kenny Chesney
    85.  Amazed – Lonestar
    86.  Sometimes – …Baby – Britney Spears
    87.  Ghetto Cowboy – Mo Thugs Family featuring Bone Thugs-N-Harmony
    88.  Out of My Head – Fastball
    89.  Hard Knock Life (Ghetto Anthem) – Jay-Z
    90.  Jamboree – Naughty By Nature featuring Zhane
    91.  Take Me There – BLACKstreet and Mya featuring Mase and Blinky Blink
    92.  Stay the Same – Joey McIntyre
    93.  Lesson In Leavin’ – Jo Dee Messina
    94.  Iris – Goo Goo Dolls
    95.  Satisfy You – Puff Daddy featuring R. Kelly
    96.  Better Days (And the Bottom Drops Out) – Citizen King
    97.  Music of My Heart – ‘N Sync and Gloria Estefan
    98.  Write This Down – George Strait
    99.  When You Believe – Whitney Houston and Mariah Carey
    100.  God Must Have Spent a Little More Time On You – Alabama featuring ‘N Sync

Looking For More Great Music From The 90s and 2000s?

If so, check out our thoughts on the Best Counting Crows Songs of All Time, the Best Barenaked Ladies Songs of All Time, the Top Staind Songs of All Time, the Best 3 Doors Down Songs, the Best 90s Rock Songs, and the Best 90s Rock Bands for more incredible song selections.

Top 100 Songs of 1999 – Final Thoughts

The top songs of 1999 encapsulated the spirit of the late ’90s, offering a mix of infectious pop, R&B, and alternative rock. Cher’s comeback anthem “Believe” dominated the airwaves with its pioneering use of Auto-Tune. Britney Spears continued her rise to superstardom with the catchy hit “Baby One More Time.” The alternative rock scene thrived with the likes of Red Hot Chili Peppers’ “Scar Tissue” and Smash Mouth’s feel-good anthem “All Star.” R&B and hip-hop were represented by TLC’s empowering “No Scrubs” and Eminem’s provocative “My Name Is.” With its eclectic blend of genres, the top songs of 1999 showcased the diverse sounds that defined the end of the millennium.