Billboard Year-End Hot 100 singles of 1999

This is a list of Billboard magazine's Top Hot 100 songs of 1999.

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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.