The 5 very sad songs that make you cry are those songs that make you want to weep like a little baby because your feelings have been made raw. They are also songs that put into words and forms of expressions feelings that you have, but which you are not capable of communicating yourself in an intelligible way.
- "Down In A Hole." While songs from metal and grunge musicians typically are not the first sad songs that make you cry that you can think of, "Down In A Hole" by those masters of pure, musical giftedness, Alice In Chains with their original lineup that includes the late, great Layne Staley, is just the song to do it. "Down In A Hole" has been misinterpreted by some to be about the late, great Layne Staley's long-term drug addiction that finally killed him in 2002, but it was in fact a Jerry Cantrell-penned song about dying relationships. The beauty of Alice In Chains is how their songs are open to be applied as you like.
"On Bended Knee." From Boyz II Men (remember them?), "On Bended Knee" holds the very lofty distinction of taking over the top spot on the Billboard Hot 100 from the previous Boyz II Mens single, "I'll Make Love To You." This was the first time a band had ever achieved this, but as for the message in "On Bended Knee," it is clearly about men desperately trying to get their girlfriends back. Hence, the "bended knee" reference in the title, which is why it sits at number two on this very sad songs that make you cry list.
- "How Do I Live." This sad song to make you cry from 1997 was famously sung by both Trisha Yearwood and LeAnn Rimes, and it was extremely popular back in the late 1990's and even into the early 2000's. This song conveys the singer's yearning and single-minded obsession with the object of her affection, plainly declaring–in a sort of doomed, Romeo-and-Juliet sort of way–that her life has no meaning without her lover/friend/husband. Back in the late 1990's, people of all colors were throwing themselves pity parties to this song.
- "Black." "Black" was one of another grunge band's, Pearl Jam, biggest hits that came off of their debut album, "Ten." The high content of grunge bands contributing to this list of very sad songs to make you cry is indicative of the grunge scene's obsession with drug-taking and the gloomy weather in Seattle. "Black" is a song that was supposed to have made some Pearl Jam fans who were contemplating suicide stop from actually going through with said self-destructive act, so while a very sad song about loss and yearning, it has actually had healing effects, too, on account of its pure awesomeness.
- "The Show Must Go On." From the greatest British band (and some would say even the greatest band of all time), the legendary Queen, comes this very sad song to make you cry. You can't help not avoid feelings of morose sadness while listening to this song since it has essentially been consistently interpreted as the late, great Freddie Mercury's resolve to continue performing, even though he's approaching his death due to AIDS.