List of Billboard Hot 100 number - one singles of 1999 - wikipedia List of Billboard Hot 100 number - one singles of 1999 Santana 's `` Smooth '' was the longest - running single of 1999, topping the chart for 10 consecutive weeks. The Billboard Hot 100 is a chart that ranks the best singles of the United States. Published by Billboard magazine, the data are compiled by Nielsen SoundScan based collectively on each single 's weekly physical sales and airplays. There were 15 singles that topped the chart this year. The first of these, `` I 'm Your Angel '' by R. Kelly and Celine Dion, spent two weeks at the top, concluding a six - week run that had begun in December 1998. During the year, 12 acts had achieved a first U.S. number - one single, including : Britney Spears, Christina Aguilera, Destiny 's Child, Enrique Iglesias, Jennifer Lopez, and Jay - Z. The longest running number - one single is `` Smooth '' by Santana featuring Rob Thomas, which attained 12 weeks at number - one. Ten of those weeks were logged in 1999 and two additional weeks were logged in 2000. Contents 1 Chart history 2 See also 3 References 4 Additional sources Chart history Pop singer Cher earned her 4th number - one single when `` Believe '' topped the chart. Pop singer Christina Aguilera earned her first U.S. number - one single, `` Genie in a Bottle ''. Pop singer Britney Spears earned her first U.S. number - one peak with ``... Baby One More Time ''. Singer Ricky Martin earned his first U.S. number - one single with `` Livin ' la Vida Loca ''. Key Indicates best - performing single of 1999 Issue Date Song Artist ( s ) Reference January 2 `` I 'm Your Angel '' R. Kelly and 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 featuring 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 featuring Jay - Z October 16 October 23 `` Smooth '' Santana featuring Rob Thomas October 30 November 6 November 13 November 20 November 27 December 4 December 11 December 18 December 25 See also 1999 in music List of number - one hits ( United States ) Billboard Year - End Hot 100 singles of 1999 List of Billboard Hot 100 top 10 singles in 1999 References Jump up ^ `` The Hot 100 chart listing for the week of January 2, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of January 9, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of January 16, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of January 23, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of January 30, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of February 6, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of February 13, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of February 20, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of February 27, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of March 6, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of March 13, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of March 20, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of March 27, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of April 3, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of April 10, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of April 17, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of April 24, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of May 1, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of May 8, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of May 15, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of May 22, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of May 29, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of June 5, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of June 12, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of June 19, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of June 26, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of July 3, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of July 10, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of July 17, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of July 24, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of July 31, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of August 7, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of August 14, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of August 21, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of August 28, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` Boys Still ' Larger Than Life ' On Billboard 200 ''. Billboard. Nielsen Business Media, Inc. 1999 - 08 - 19. Archived from the original on February 10, 2009. Retrieved 2009 - 01 - 24. Jump up ^ `` The Hot 100 chart listing for the week of September 4, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of September 11, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of September 18, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of September 25, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of October 2, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of October 9, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` Mariah Scores 14th No. 1 Single ''. Billboard. Nielsen Business Media, Inc. 1999 - 09 - 30. Retrieved 2009 - 05 - 05. Jump up ^ `` The Hot 100 chart listing for the week of October 16, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of October 23, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of October 30, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of November 6, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of November 13, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of November 20, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of November 27, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of December 4, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of December 11, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of December 18, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Jump up ^ `` The Hot 100 chart listing for the week of December 25, 1999 ''. Billboard. Nielsen Business Media, Inc. Retrieved 2010 - 04 - 23. Additional sources Fred Bronson 's Billboard Book of Number 1 Hits, 5th Edition ( ISBN 0 - 8230 - 7677 - 6 ) Joel Whitburn 's Top Pop Singles 1955 - 2008, 12 Edition ( ISBN 0 - 89820 - 180 - 2 ) Joel Whitburn Presents the Billboard Hot 100 Charts : The Nineties ( ISBN 0 - 89820 - 137 - 3 ) Additional information obtained can be verified within Billboard 's online archive services and print editions of the magazine. Lists of Billboard number - one singles 1940 -- 1959 1940 1941 1942 1943 1944 1945 1946 1947 1948 1949 1950 1951 1952 1953 1954 1955 1956 1957 1958 1959 1960 -- 1979 1960 1961 1962 1963 1964 1965 1966 1967 1968 1969 1970 1971 1972 1973 1976 1977 1978 1979 1980 -- 1999 1980 1981 1982 1984 1985 1986 2000 -- present 2017 2018 By decade 1930s 1940s 1950 -- 1958 1958 -- 1969 1970s 1980s 1990s 2000s 2010s See also Top - ten singles Hot 100 Year - end List of Billboard Hot 100 chart achievements and milestones Retrieved from `` https://en.wikipedia.org/w/index.php?title=List_of_Billboard_Hot_100_number-one_singles_of_1999&oldid=826585969 '' Categories : 1999 record charts Lists of Billboard Hot 100 number - one songs Hidden categories : All articles with dead external links Articles with dead external links from October 2010 Wikipedia indefinitely semi-protected pages Talk View source Contents About Wikipedia Čeština Deutsch Español Français Bahasa Indonesia Italiano Nederlands Polski Português Русский Svenska Türkçe Tiếng Việt 4 more Edit links This page was last edited on 19 February 2018, at 23 : 26 ( UTC ). 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Question: what song was number 1 on december 12 1999
Answer: Smooth