Our next artist also had her major breakthrough in 1996 before becoming her generation’s next Anita Baker. While she’s had plenty of other great R&B hits, this song remains one of her all-time classics. The chorus remains indelible while at the same time heart-wrenching, and it remains one of the biggest slow R&B songs of the 90s. Coming in at #19 is Un-break My Heart by Toni Braxton.

We begin our countdown of the top 20 songs turning 30 years old this year with an artist that essentially made her mainstream debut in 1996.  While an acquired taste for some, her songs remain a key fixture in both pop culture and adult contemporary music. While another song from this initial album might have been bigger, that wouldn’t come about until the following year. But this year, 1996, this song broke through and starts our list at #20 – it’s You Were Meant For Me by Jewel.

We have finally come to the #1 songs, and what song could possibly supersede the all-time Billboard chart classic?  This one.  Given the subject matter, it’s incredibly hooky chorus, and the fact it has remained a staple of the hip-hop/R&B music scene for decades, it’s hard not to put this song as the top song released in 1995.  The #1 song turning 30 years old this year is – Waterfalls by TLC.

For more than two decades, this song held the record for being the longest reigning number 1 song in Billboard chart history.  The fact it took that long for its record to be displaced speaks volumes.  This band (who has made numerous appearances in prior countdowns) and this artist were collectively, arguably, the biggest R&B stars of the time, and this song is a high marker, but just not #1.  At #2 it’s One Sweet Day by Boyz II Men & Mariah Carey.

As soon as the vocals hit, you know what song it is and you’re ready to start dancing.  One of the biggest hip-hop/R&B songs of the 90s, it has never lost its luster and continues to be heard from TV commericials, to sports arenas and backyard parties.  Coming in at #3 is This Is How We Do It by Montell Jordan.

Despite the controversy this group carried throughout their existence, it is hard not to consider them one of the most iconic pop/rock groups of the 90s, and this song remains one of their most celebrated tracks.  Even when you think they are faded, playing this track reignites their flame and notifies us they have been great songwriters.  At #4 it’s Wonderwall by Oasis.