Billboard Year-End Hot 100 singles of 1999 From Wikipedia the free encyclopedia Cher (pictured) topped the list with "Believe" after the song was number one on the Hot 100 chart for four weeks, making her the oldest female artist to top the chart. It also gave her her first number one on the Hot 100 since "Dark Lady" in 1974, giving her the longest gap between number ones at nearly 25 years. Whitney Houston (pictured) had four songs, all of which came from her 1998 album My Love Is Your Love, on the Year-End chart, the most of any artist that year. These included "Heartbreak Hotel" at number four, "It's Not Right but It's Okay" at number 44, "My Love Is Your Love" at number 73, and "When You Believe" with Mariah Carey at number 99. "I Still Believe" and "When You Believe", two singles by Mariah Carey (pictured) from her 1998 compilation album #1's, made it onto the Year-End list at numbers 36 and 99, respectively, while her song "Heartbreaker" placed at number 35. Two singles by Faith Evans (pictured) from her 1998 album Keep the Faith—"Love Like This" and "All Night Long"—appeared on the Year-End list at numbers 58 and 74, respectively. Evans was also featured on "Heartbreak Hotel", which appeared at number four on the list. This is a list of Billboard magazine's Top Hot 100 songs of 1999.[1] No. Title Artist(s) 1 "Believe" Cher 2 "No Scrubs" TLC 3 "Angel of Mine" Monica 4 "Heartbreak Hotel" Whitney Houston featuring Faith Evans and Kelly Price 5 "...Baby One More Time" Britney Spears 6 "Kiss Me" Sixpence None the Richer 7 "Genie in a Bottle" Christina Aguilera 8 "Every Morning" Sugar Ray 9 "Nobody's Supposed to Be Here" Deborah Cox 10 "Livin' la Vida Loca" Ricky Martin 11 "Where My Girls At?" 702 12 "If You Had My Love" Jennifer Lopez 13 "Slide" Goo Goo Dolls 14 "Have You Ever?" Brandy 15 "I Want It That Way" Backstreet Boys 16 "I'm Your Angel" R. Kelly and Celine Dion 17 "All Star" Smash Mouth 18 "Angel" Sarah McLachlan 19 "Smooth" Santana featuring Rob Thomas 20 "Unpretty" TLC 21 "Bills, Bills, Bills" Destiny's Child 22 "Save Tonight" Eagle-Eye Cherry 23 "Last Kiss" Pearl Jam 24 "Fortunate" Maxwell 25 "All I Have to Give" Backstreet Boys 26 "Bailamos" Enrique Iglesias 27 "What's It Gonna Be?!" Busta Rhymes featuring Janet 28 "What It's Like" Everlast 29 "Fly Away" Lenny Kravitz 30 "Someday" Sugar Ray 31 "Lately" Divine 32 "That Don't Impress Me Much" Shania Twain 33 "Wild Wild West" Will Smith featuring Dru Hill and Kool Moe Dee 34 "Scar Tissue" Red Hot Chili Peppers 35 "Heartbreaker" Mariah Carey featuring Jay-Z 36 "I Still Believe" Mariah Carey 37 "The Hardest Thing" 98 Degrees 38 "Summer Girls" LFO 39 "Can I Get A..." Jay-Z featuring Amil and Ja Rule 40 "Jumper" Third Eye Blind 41 "Doo Wop (That Thing)" Lauryn Hill 42 "Mambo No. 5" Lou Bega 43 "Sweet Lady" Tyrese 44 "It's Not Right but It's Okay" Whitney Houston 45 "(God Must Have Spent) A Little More Time on You" NSYNC 46 "Lullaby" Shawn Mullins 47 "Anywhere" 112 featuring Lil Zane 48 "Tell Me It's Real" K-Ci & JoJo 49 "Back 2 Good" Matchbox 20 50 "808" Blaque 51 "She's So High" Tal Bachman 52 "She's All I Ever Had" Ricky Martin 53 "Miami" Will Smith 54 "Hands" Jewel 55 "Who Dat" JT Money featuring Solé 56 "Please Remember Me" Tim McGraw 57 "From This Moment On" Shania Twain 58 "Love Like This" Faith Evans 59 "You" Jesse Powell 60 "Trippin'" Total featuring Missy Elliott 61 "If You" Silk 62 "Ex-Factor" Lauryn Hill 63 "Give It to You" Jordan Knight 64 "Black Balloon" Goo Goo Dolls 65 "Spend My Life with You" Eric Benét featuring Tamia 66 "These Are the Times" Dru Hill 67 "I Don't Want to Miss a Thing" Mark Chesnutt 68 "I Do (Cherish You)" 98 Degrees 69 "Because of You" 70 "I Will Remember You" Sarah McLachlan 71 "Chanté's Got a Man" Chanté Moore 72 "Happily Ever After" Case 73 "My Love Is Your Love" Whitney Houston 74 "All Night Long" Faith Evans featuring Puff Daddy 75 "Back That Thang Up" Juvenile featuring Mannie Fresh and Lil Wayne 76 "Almost Doesn't Count" Brandy 77 "Man! I Feel Like a Woman!" Shania Twain 78 "Steal My Sunshine" Len 79 "I Need to Know" Marc Anthony 80 "So Anxious" Ginuwine 81 "Faded Pictures" Case featuring Joe 82 "Back at One" Brian McKnight 83 "When a Woman's Fed Up" R. Kelly 84 "How Forever Feels" Kenny Chesney 85 "Amazed" Lonestar 86 "Sometimes" Britney Spears 87 "Ghetto Cowboy" Mo Thugs 88 "Out of My Head" Fastball 89 "Hard Knock Life (Ghetto Anthem)" Jay-Z 90 "Jamboree" Naughty by Nature featuring Zhané 91 "Take Me There" Blackstreet featuring Mýa, Mase and Blinky Blink 92 "Stay the Same" Joey McIntyre 93 "A Lesson in Leavin'" Jo Dee Messina 94 "Iris" Goo Goo Dolls 95 "Satisfy You" Puff Daddy featuring R. Kelly 96 "Better Days (And the Bottom Drops Out)" Citizen King 97 "Music of My Heart" NSYNC and Gloria Estefan 98 "Write This Down" George Strait 99 "When You Believe" Whitney Houston and Mariah Carey 100 "(God Must Have Spent) A Little More Time on You" Alabama and NSYNC See also[edit] 1999 in music List of Billboard Hot 100 number-one singles of 1999 List of Billboard Hot 100 top-ten singles in 1999 References[edit] ^ "1999 The Year in Music: Hot 100 Singles". Billboard. December 25, 1999. pp. YE48, YE50. Retrieved June 18, 2017. vteBillboard Year-End Hot 100 singles1946–1949 1946 1947 1948 1949 1950–1969 1950 1951 1952 1953 1954 1955 1956 1957 1958 1959 1960 1961 1962 1963 1964 1965 1966 1967 1968 1969 1970–1989 1970 1971 1972 1973 1974 1975 1976 1977 1978 1979 1980 1981 1982 1983 1984 1985 1986 1987 1988 1989 1990–2009 1990 1991 1992 1993 1994 1995 1996 1997 1998 1999 2000 2001 2002 2003 2004 2005 2006 2007 2008 2009 2010–present 2010 2011 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 2023