EVERY Billboard Hot 100 #1 Hit of 1999

There were 15 different songs that reached the top of the Billboard Hot 100 chart in 1999. Given the artist and their respective issue dates, can you name every song?

The weeks are listed as "issue date," meaning the song was at #1 when the list was published on that Saturday

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Last updated: October 5, 2025

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First submitted	October 5, 2025
Times taken	5
Average score	55.8%
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Issue Date	#1 Hit	Artist
January 2	I'm Your Angel	R. Kelly & Céline Dion
January 9
January 16	Have You Ever?	Brandy
January 23
January 30	...Baby One More Time	Britney Spears
February 6
February 13	Angel of Mine	Monica
February 20
February 27
March 6
March 13	Believe	Cher
March 20
March 27
April 3
April 10	No Scrubs	TLC
April 17
April 24
May 1
May 8	Livin' la Vida Loca	Ricky Martin
May 15
May 22
May 29
June 5
June 12	If You Had My Love	Jennifer Lopez
June 19
June 26
July 3
July 10
July 17	Bills, Bills, Bills	Destiny's Child
July 24	Wild Wild West	Will Smith ft. Dru Hill and Kool Moe Dee
July 31	Genie in a Bottle	Christina Aguilera
August 7
August 14
August 21
August 28
September 4	Bailamos	Enrique Iglesias
September 11
September 18	Unpretty	TLC
September 25
October 2
October 9	Heartbreaker	Mariah Carey ft. Jay-Z
October 16
October 23	Smooth	Santana ft. Rob Thomas
October 30
November 6
November 13
November 20
November 27
December 4
December 11
December 18
December 25