Hit play. Dim the lights. And try not to tear up when the saxophone kicks in. [Full list of 100 songs available below—organized by year, key change intensity, and "crying in the car" viability.]
You will find Boyz II Men on the list seven times. You will find Aerosmith’s "I Don’t Want to Miss a Thing" (Armageddon edition). You will find that one Hootie & the Blowfish song you forgot you loved.
The breakup anthem for when you know it’s over, but you refuse to admit it. It’s the song you played on repeat while laying on your bedroom floor carpet. It holds the record for longest #1 hit (13 weeks) because the 90s were collectively heartbroken.
The tear. The single tear rolling down her cheek in the video. This song stripped away all the production. No boy band harmonies. No sax solo. Just a shaved head, a black turtleneck, and the raw realization that Prince wrote the perfect breakup song.