Popsugar Entertainment Nostalgia Saddest Songs of 2000 40+ Songs From the Year 2000 That'll Get You All Up in Your Feels 20 December 2019 by Olivia Luchini View On One Page Photo 4 of 43 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 4 "He Wasn't Man Enough" by Toni Braxton It's about post-breakup confidence, but it can definitely be a good song for a post-breakup cry. Previous Next Start Slideshow NostalgiaMusic