1999

Issue date 	Song 	Artist(s)
January 2 	"I'm Your Angel" 	Céline Dion and R. Kelly
January 9 	"...Baby One More Time" 	Britney Spears
January 16 	"...Baby One More Time" 	Britney Spears
January 23 	"...Baby One More Time" 	Britney Spears
January 30 	"...Baby One More Time" 	Britney Spears
February 6 	"...Baby One More Time" 	Britney Spears
February 13 	"...Baby One More Time" 	Britney Spears
February 20 	"...Baby One More Time" 	Britney Spears
February 27 	"Pretty Fly (For a White Guy)" 	The Offspring
March 6 	"Fly Away" 	Lenny Kravitz
March 13 	"Believe" 	Chér
March 20 	"Believe" 	Chér
March 27 	"Believe" 	Chér
April 3 	"Believe" 	Chér
April 10 	"Maria" 	Blondie
April 17 	"No Scrubs" 	TLC
April 24 	"No Scrubs" 	TLC
May 1 	"No Scrubs" 	TLC
May 8 	"No Scrubs" 	TLC
May 15 	'"Kiss Me"' 	Sixpence None the Richer
May 22 	'"Kiss Me"' 	Sixpence None the Richer
May 29 	"Livin' la Vida Loca" 	Ricky Martin
June 5 	"Livin' la Vida Loca" 	Ricky Martin
June 12 	"Livin' la Vida Loca" 	Ricky Martin
June 19 	"Livin' la Vida Loca" 	Ricky Martin
June 26 	"Livin' la Vida Loca" 	Ricky Martin
July 3 	"If You Had My Love" 	Jennifer Lopez
July 10 	"If You Had My Love" 	Jennifer Lopez
July 17 	"If You Had My Love" 	Jennifer Lopez
July 24 	"Bills, Bills, Bills" 	Destiny's Child
July 31 	"Wild Wild West" 	Will Smith featuring Dru Hill and Kool Moe Dee
August 7 	"I Want It That Way" 	Backstreet Boys
August 14 	"I Want It That Way" 	Backstreet Boys
August 21 	"I Want It That Way" 	Backstreet Boys
August 28 	"I Want It That Way" 	Backstreet Boys
September 4 	"I Want It That Way" 	Backstreet Boys
September 11	"I Want It That Way" 	Backstreet Boys
September 18	"Genie in a Bottle" 	Christina Aguilera
September 25	"Genie in a Bottle" 	Christina Aguilera
October 2 	"Genie in a Bottle" 	Christina Aguilera
October 9 	"All Star" 	Smash Mouth
October 16 	"Bailamos" 	Enrique Iglesias
October 23 	"Bailamos" 	Enrique Iglesias
October 30 	"Unpretty" 	TLC
November 6 	"Heartbreaker" 	Mariah Carey featuring Jay-Z
November 13 	"Heartbreaker" 	Mariah Carey featuring Jay-Z
November 20 	"Mambo No. 5 (A Little Bit Of...)"	Lou Bega
November 27 	"Mambo No. 5 (A Little Bit Of...)"	Lou Bega
December 4 	"Smooth" 	Santana featuring Rob Thomas
December 11 	"Smooth" 	Santana featuring Rob Thomas
December 18 	"Smooth" 	Santana featuring Rob Thomas
December 25 	"Smooth" 	Santana featuring Rob Thomas