40+ Songs From the Year 2000 That'll Get You All Up in Your Feels

While the year 2000 is generally defined by Britney Spears and the Backstreet Boys hip-hopping across stages and making listeners want to do the same, there are plenty of songs that topped charts in 2000 that make us want to look out a window on a rainy day and gently touch our hands against the glass, contemplating life. Yes, sad songs certainly did exist in the world of low-rise jeans, velour tracksuits, and denim disasters, and a lot of them are still bops to this day. Here's a compilation of songs that sound sad or talk about sad, sad things to add to your 2020 playlists.