The Number One Hits Of 1999

December 5, 1998 – January 15, 1999
R. Kelly & Celine Dion
I’m Your Angel
R. Kelly is known for writing and producing numerous successful R&B, pop, and gospel songs. Celine Dion has won numerous awards, including five Grammy Awards.
I’m Your Angel was nominated for a Grammy Award for Best Pop Collaboration with Vocals in 1999.
January 16, 1999 – January 29, 1999
Have You Ever
Brandy Norwood is an American singer, songwriter, and actress who gained fame in the 1990s.
Have You Ever is a heartfelt ballad about unrequited love and longing for someone.
January 30, 1999 – February 12, 1999
Britney Spears
…Baby One More Time
Britney Spears is an influential pop icon who has sold over 100 million records worldwide.
…Baby One More Time is Britney’s debut single and became an instant pop classic.
February 13, 1999 – March 12, 1999
Angel Of Mine
Monica Denise Arnold is an American R&B singer and actress who debuted in the music industry in the mid-1990s.
Angel Of Mine covers the original song by the British girl group Eternal.
March 13, 1999 – April 9, 1999
Cher is a legendary singer and actress with a career spanning over six decades.
Believe introduced Auto-Tune as a creative vocal effect and became a dance-pop anthem.
April 10, 1999 – May 7, 1999
No Scrubs
TLC is an American girl group known for blending R&B, hip-hop, and pop music.
No Scrubs is an empowering anthem that addresses men who lack ambition or financial stability.
May 8, 1999 – June 11, 1999
Ricky Martin
Livin’ La Vida Loca
Ricky Martin is a Puerto Rican singer, actor, and author who gained international fame in the late 1990s.
Livin’ La Vida Loca is an energetic Latin pop song that helped launch the Latin music boom of the late 1990s.
June 12, 1999 – July 16, 1999
Jennifer Lopez
If You Had My Love
Jennifer Lopez is an American singer, actress, and businesswoman who has released numerous successful albums and singles.
If You Had My Love is Jennifer Lopez’s debut single, establishing her as a pop sensation.
July 17, 1999 – July 23, 1999
Destiny’s Child
Bills, Bills, Bills
Destiny’s Child is an American girl group that launched the careers of Beyoncé, Kelly Rowland, and Michelle Williams.
Bills, Bills, Bills is a catchy R&B song about financial independence and self-respect.
July 24, 1999 – July 30, 1999
Will Smith featuring Dru Hill & Kool Moe Dee
Wild Wild West
Will Smith is an American actor, rapper, and producer known for his successful film and music career. Dru Hill is an American R&B group, and Kool Moe Dee is a pioneering hip-hop artist.
Wild Wild West is the theme song for the film of the same name, in which Will Smith starred.
July 31, 1999 – September 3, 1999
Christina Aguilera
Genie In A Bottle
Christina Aguilera is an American singer, songwriter, and actress who rose to fame in the late 1990s.
Genie In A Bottle is Aguilera’s debut single, a pop and dance hit worldwide.
September 4, 1999 – September 17, 1999
Enrique Iglesias
Enrique Iglesias is a Spanish singer, songwriter, and actor known for his Latin and English-language pop hits.
Bailamos was featured in “Wild Wild West” and became an international hit.
September 18, 1999 – October 8, 1999
TLC is an American girl group known for blending R&B, hip-hop, and pop music.
Unpretty is a song about self-esteem and self-worth, addressing societal beauty standards.
October 9, 1999 – October 22, 1999
Mariah Carey featuring Jay-Z
Mariah Carey is a renowned American singer and songwriter. Jay-Z is an American rapper, entrepreneur, and record executive.
Heartbreaker is a catchy pop and R&B song about a woman confronting a cheating partner.
October 23, 1999 – January 14, 2000
Santana featuring Rob Thomas
Santana is a legendary rock band led by guitarist Carlos Santana. Rob Thomas is the lead vocalist of the band Matchbox Twenty.
Smooth is a Latin rock song that became a massive hit and won three Grammy Awards.

The Biggest Pop Artists of 1999 include:
Backstreet Boys, Brad Paisley, Brandy, Brian McKnight, Britney Spears, B*Witched, Cher, Christina Aguilera, Deborah Cox, Destiny’s Child, Eminem, Enrique Iglesias, Eve, Faith Evans, Ja Rule, Jay-Z, Jennifer Lopez, Jessica Simpson, Kelly Price, Lauryn Hill, Mariah Carey, Missy ‘Misdemeanor’ Elliott, Montell Jordan, Nas, 98°, *NSYNC, Pearl Jam, Puff Daddy, Q-Top, R. Kelly, Ricky Martin, Rob Thomas, Santana, Shania Twain, Smash Mouth, Sugar Ray, TLC, Vengaboys, Whitney Houston, Will Smith, Wyclef Jean

(HPS music data is compiled from charts, including Billboard’s Pop, Rock, Airplay, R&B/Dance, and Singles Charts. The Hot 100 is the primary chart used for this list.)


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