1999 Billboard Number One Hits: Every Hot 100 Chart-Topper

The 1999 Billboard Number One Hits list closed the decade with teen-pop breakthroughs, R&B dominance, Latin-pop crossover, veteran comebacks, and one very smooth Santana revival. Britney Spears and Christina Aguilera arrived at No. 1, Ricky Martin and Jennifer Lopez helped push Latin pop into the U.S. mainstream, TLC returned with two chart-toppers, and Cher scored one of the most memorable late-career No. 1 hits in pop history.

This page follows the Billboard Hot 100 issue dates for 1999, shown here as reader-friendly weekly date ranges. Because Billboard chart weeks can cross calendar years, this list begins with R. Kelly and Céline Dion’s late-1998 carryover and continues into early 2000 with Santana and Rob Thomas’ Smooth.

The Billboard Hot 100 ranks the most popular songs in the United States using radio airplay, sales, and later streaming activity. These are official Billboard Hot 100 No. 1 songs, not pop-only, rock-only, airplay-only, R&B-only, dance-only, or “this was absolutely playing during every trip to the mall” rankings.

1999 Billboard Number One Hits by Week

December 27, 1998 – January 9, 1999: I’m Your Angel – R. Kelly & Céline Dion
January 10 – January 23, 1999: Have You Ever? – Brandy
January 24 – February 6, 1999: …Baby One More Time – Britney Spears
February 7 – March 6, 1999: Angel of Mine – Monica
March 7 – April 3, 1999: Believe – Cher
April 4 – May 1, 1999: No Scrubs – TLC
May 2 – June 5, 1999: Livin’ la Vida Loca – Ricky Martin
June 6 – July 10, 1999: If You Had My Love – Jennifer Lopez
July 11 – July 17, 1999: Bills, Bills, Bills – Destiny’s Child
July 18 – July 24, 1999: Wild Wild West – Will Smith featuring Dru Hill & Kool Moe Dee
July 25 – August 28, 1999: Genie in a Bottle – Christina Aguilera
August 29 – September 11, 1999: Bailamos – Enrique Iglesias
September 12 – October 2, 1999: Unpretty – TLC
October 3 – October 16, 1999: Heartbreaker – Mariah Carey featuring Jay-Z
October 17, 1999 – January 8, 2000: Smooth – Santana featuring Rob Thomas

Song-by-Song Notes on the 1999 Billboard No. 1 Hits

I’m Your Angel – R. Kelly & Céline Dion

I’m Your Angel opened the 1999 Billboard Hot 100 calendar after beginning its No. 1 run in late 1998. The duet paired R. Kelly with Céline Dion, combining R&B songwriting with adult-contemporary ballad power.

Its early-January placement gave 1999 a slow, sentimental start before the year shifted quickly into teen pop, R&B, Latin crossover, and dance-pop comebacks. It was the calm before the Britney-shaped storm.

Have You Ever? – Brandy

Brandy reached No. 1 with Have You Ever?, a Diane Warren-written ballad from her album Never Say Never. The song gave Brandy another major Hot 100 moment after her 1998 success with Monica on The Boy Is Mine.

Its two-week run kept late-1990s R&B balladry near the top of the chart. Brandy’s vocal restraint helped make the song feel intimate rather than oversized.

…Baby One More Time – Britney Spears

Britney Spears earned her first Hot 100 No. 1 with …Baby One More Time. The song’s Max Martin production, school-hall video, and instantly recognizable opening helped launch one of the biggest teen-pop careers of the late 1990s and early 2000s.

Its two-week run was short compared with its cultural impact. This was not just a No. 1 single; it was a pop-culture starting whistle with pigtails and a key change.

Angel of Mine – Monica

Monica reached No. 1 with Angel of Mine, a ballad originally recorded by British group Eternal. Her version became one of 1999’s biggest R&B-pop crossover hits.

The song spent four weeks at No. 1 and ranked No. 3 on Billboard’s year-end Hot 100 for 1999. It gave Monica another major solo moment after the enormous success of The Boy Is Mine.

Believe – Cher

Cher’s Believe spent four weeks at No. 1 and became Billboard’s year-end Hot 100 song of 1999. Its dance-pop production and famous Auto-Tune vocal effect helped make it one of the most influential pop singles of the late 1990s.

The song also made Cher the oldest female artist to top the Hot 100 at that time. It was a comeback, a club hit, and a production milestone all at once. Not bad for a song that asked one very dramatic question and then answered it with a beat.

No Scrubs – TLC

TLC returned to No. 1 with No Scrubs, a sharp R&B-pop anthem from FanMail. The song’s direct lyrics, sleek production, and unforgettable hook made it one of 1999’s defining hits.

It spent four weeks at No. 1 and finished as Billboard’s No. 2 Hot 100 song of the year. The word “scrub” did not start with the song, but TLC made sure nobody used it the same way again.

Livin’ la Vida Loca – Ricky Martin

Ricky Martin reached No. 1 with Livin’ la Vida Loca, one of the central Latin-pop crossover hits of 1999. The song’s horn-driven pop-rock energy, bilingual-friendly title, and charismatic performance helped introduce Martin to a massive English-language U.S. audience.

Its five-week run made it one of the year’s biggest chart moments and helped frame 1999 as a breakthrough year for Latin pop in the mainstream Hot 100 conversation.

If You Had My Love – Jennifer Lopez

Jennifer Lopez earned her first Hot 100 No. 1 with her debut single If You Had My Love. The song’s smooth pop-R&B production and video-heavy rollout helped move Lopez from film stardom into music stardom.

It spent five weeks at No. 1 and became one of the year’s strongest debut singles. The transition from movie star to pop star is not always smooth, but this one landed directly on top of the chart.

Bills, Bills, Bills – Destiny’s Child

Destiny’s Child reached No. 1 for the first time with Bills, Bills, Bills. The song’s staccato production, group harmonies, and sharply worded financial frustration helped define the group’s late-1990s breakout sound.

Its one-week run was brief, but its importance was much larger. Destiny’s Child would become one of the central pop/R&B groups of the next several years.

Wild Wild West – Will Smith featuring Dru Hill & Kool Moe Dee

Will Smith reached No. 1 with Wild Wild West, featuring Dru Hill and Kool Moe Dee. The song came from the film Wild Wild West and reworked elements from Stevie Wonder’s I Wish into a movie-friendly rap-pop single.

Its one-week run continued Smith’s late-1990s streak of soundtrack-linked pop hits. The movie had its problems, but the single still rode straight to No. 1.

Genie in a Bottle – Christina Aguilera

Christina Aguilera earned her first Hot 100 No. 1 with Genie in a Bottle. The song’s sleek teen-pop production, strong vocal performance, and slightly more mature edge helped distinguish her from the broader teen-pop wave.

It spent five weeks at No. 1 and made Aguilera one of 1999’s biggest new artists. The bottle opened, and the chart got a new powerhouse vocalist.

Bailamos – Enrique Iglesias

Enrique Iglesias reached No. 1 with Bailamos, a Latin-pop crossover single connected to the film Wild Wild West. The song helped introduce Iglesias to a wider English-language U.S. audience.

Its two-week run added to 1999’s Latin-pop wave, alongside Ricky Martin and Jennifer Lopez. By late summer, the Hot 100 had clearly made room for a much broader pop sound.

Unpretty – TLC

TLC scored their second No. 1 of 1999 with Unpretty. The song’s lyrics addressed beauty standards, insecurity, and self-image, giving the group a more reflective chart-topper after the sharp attitude of No Scrubs.

Its three-week run showed TLC’s range within the same album era. They could call out scrubs in spring and still deliver one of the year’s most thoughtful pop/R&B singles by fall.

Heartbreaker – Mariah Carey featuring Jay-Z

Mariah Carey reached No. 1 with Heartbreaker, featuring Jay-Z. The song continued Carey’s late-1990s blend of pop, R&B, and hip-hop collaboration.

Its two-week run gave Carey another Hot 100 chart-topper and added Jay-Z to the list of artists earning their first No. 1 credit in 1999. The song was glossy, playful, and very much part of Carey’s remix-era pop identity.

Smooth – Santana featuring Rob Thomas

Santana and Rob Thomas closed the 1999 Billboard Hot 100 year with Smooth, which carried into January 2000. The song mixed Santana’s Latin-rock guitar with Thomas’ pop-rock vocal style, creating one of the most successful cross-generational collaborations of the decade.

Smooth spent 12 total weeks at No. 1, the longest run connected to the 1999 chart year. It also helped power Santana’s massive Supernatural comeback and became one of the signature songs at the turn of the millennium.

Biggest Billboard Hot 100 Stories of 1999

Believe Was Billboard’s Year-End No. 1

Cher’s Believe finished as Billboard’s top Hot 100 song of 1999. Its dance-pop sound and Auto-Tune vocal effect helped reshape how pop production would sound in the years that followed.

Teen Pop Fully Arrived

Britney Spears and Christina Aguilera both earned their first Hot 100 No. 1 songs in 1999. Their breakthroughs helped define the teen-pop explosion that carried into the early 2000s.

Latin Pop Had a Landmark Year

Ricky Martin, Jennifer Lopez, and Enrique Iglesias all reached No. 1 in 1999. Their success helped make Latin-pop crossover one of the year’s biggest mainstream music stories.

TLC Had a Major Comeback

TLC scored two No. 1 songs in 1999 with No Scrubs and Unpretty. Together, those singles gave FanMail both attitude and emotional depth.

Santana Bridged the Decade

Smooth began its No. 1 run in October 1999 and carried into January 2000. It helped make Santana’s Supernatural one of the biggest comeback stories in modern pop and rock history.

1999 Billboard Number One Hits Trivia

Believe by Cher was Billboard’s year-end Hot 100 song of 1999.
Smooth by Santana featuring Rob Thomas spent 12 total weeks at No. 1 and carried into 2000.
…Baby One More Time gave Britney Spears her first Hot 100 No. 1.
Genie in a Bottle gave Christina Aguilera her first Hot 100 No. 1.
If You Had My Love gave Jennifer Lopez her first Hot 100 No. 1.
Bills, Bills, Bills gave Destiny’s Child its first Hot 100 No. 1.
No Scrubs and Unpretty gave TLC two No. 1 songs from FanMail.
Heartbreaker gave Jay-Z his first Hot 100 No. 1 credit.
Livin’ la Vida Loca, If You Had My Love, and Bailamos helped define the 1999 Latin-pop crossover boom.

Why the 1999 Billboard Number One Hits Matter

The 1999 Billboard Number One Hits list showed the Hot 100 at the edge of a new pop era. R&B was still strong, teen pop was exploding, Latin crossover became a major mainstream story, and veteran artists like Cher and Santana returned with era-defining hits.

The year also set up the sound of the early 2000s. Britney Spears, Christina Aguilera, Jennifer Lopez, Destiny’s Child, Enrique Iglesias, Jay-Z, and Rob Thomas all earned major No. 1 breakthroughs or crossover moments, while TLC and Mariah Carey kept established star power in the mix.

For chart fans, 1999 was a handoff year. The decade ended with pop reinvention, global crossover, R&B attitude, and Santana riding a guitar riff straight into the next millennium.