Popsugar Entertainment Playlist Best Songs From 1999 Because the '90s Are Maybe the Best Decade Ever, Here's a Fun Playlist From 1999 30 December 2019 by Emily Mallden Image Source: YouTube user Christina Aguilera There are playlists, and then there are epic playlists. We pulled up the best of 1999 — better known as one of the greatest years for iconic hit songs — for an absolutely epic playlist. Right at the cusp of the millennium, 1999 saw some of the best of boy bands, R&B, pop, and a few hybrid sounds. If you want to feel a bit nostalgic, take a look at our list of the greatest songs to belt out and dance to from 1999. Look through the hits and then flip over to Spotify to jam out any time you'd like. Just remember: you'll need to download the free Spotify software or app to listen to our playlists! "All Star" by Smash Mouth 1 / 25 "I Want It That Way" by Backstreet Boys 2 / 25 "Genie in a Bottle" by Christina Aguilera 3 / 25 "Steal My Sunshine" by Len 4 / 25 "Livin' La Vida Loca" by Ricky Martin 5 / 25 "Wild Wild West" by Will Smith feat. Dru Hill and Kool Mo Dee 6 / 25 "(You Drive Me) Crazy" by Britney Spears 7 / 25 "Mambo No. 5" by Lou Bega 8 / 25 "Say My Name" by Destiny's Child 9 / 25 "Music of My Heart" by N*Sync and Gloria Estefan 10 / 25 "Where My Girls At" by 702 11 / 25 "Larger Than Life" by Backstreet Boys 12 / 25 "All the Small Things" by Blink-182 13 / 25 "Every Morning" by Sugar Ray 14 / 25 "Higher" by Creed 15 / 25 "My Name Is" by Eminem 16 / 25 "808" by Blaque 17 / 25 "Please Remember Me" by Tim McGraw 18 / 25 "Una Noche Más" by Jennifer Lopez 19 / 25 "Beautiful Stranger" by Madonna 20 / 25 "She's All I Ever Had" by Ricky Martin 21 / 25 "Sometimes" by Britney Spears 22 / 25 "I Try" by Macy Gray 23 / 25 "Heartbreaker" by Mariah Carey and JAY-Z 24 / 25 "Learn to Fly" by Foo Fighters 25 / 25 PlaylistNostalgiaMusic