The 99 Greatest Songs of 1999: Critics’ Picks. At the end of the millennium, popular music was behaving like we really might only have one year left.

Scroll through the list of No. 1 songs in 1999, from "...Baby One More Time" to "No Scrubs" to revisit the end of the millennium.

What follows is a list of 25 songs turning 25 in 2024. It’s a testament to the wonderful weirdness of 1999, the year that gave us indelible hits by Limp Bizkit, Christina Aguilera, Macy Gray ...

But I dare you not to sing along when someone chooses “I Want It That Way” at karaoke. 1999 was the peak year for boy bands, noted by *NSYNC’s first top 10 hit and 98 Degrees’ chart ...

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 ...

SEX. Rating: 4/10. Tying with money, sex is also a hot topic in turn-of-the-century jams. But just like our country hits analysis, it's usually hinted at, but not said explicitly.

Twenty years ago in 1999, we were all "Livin La Vida Loca." It was the year when Ricky, J.Lo, Christina and Britney gave us some of the biggest hit songs of our generation.