- May 18 "Millennium" 3rd studio album by the Backstreet Boys is released - one of the best-selling albums of all time, over 30 million copies sold
- May 29 44th Eurovision Song Contest: Charlotte Nilsson for Sweden wins singing "Take Me to Your Heaven" in Jerusalem
- Jul 22 Woodstock 99 music festival begins Griffiss Park, Rome NY (till 25th) attended by 200,000. Ended due to violence.
Oct 19 "Believe" single released by Cher (Billboard Song of the Year 1999, Grammy Award Best Dance Recording 2000)
- Nov 22 "How Do You Like Me Now?!" single released by Toby Keith (Billboard Song of the Year 2000)