Though I didn't grow up during the era, I've found that the 1990s were a decade in popular music defined by death and sadness, more so than the decade before it and far more so than the decade afterwards. So many of the 1990s' most popular songs are fully-forced, emotionally impactful songs about the death of the beloved. These songs are among the most popular hits in music history, and they're made to get listeners crying.

Mariah Carey and Boyz II Men - One Sweet Day (1996)

The Sentimental 90’s Elegy Ballad had its biggest success in one of the most obvious fusions of two artists in musical history – 1995’s “One Sweet Day” by Mariah Carey and Boyz II Men. Before they collaborated, each artist had sentimental classics of their own hit number one on the Billboard Hot 100, Mariah in 1991 with “I Don’t Wanna Cry” and Boyz II Men in ’92 with “End of the Road” – and those are far from the only examples of balladic excellence from these two. This finished at the top of the year-end Hot 100 in 1996, and the top of the decade-end chart by the end of 1999. It held the number one spot down in 1996 for sixteen weeks. This formula, combining one of the most emotional female R&B singers with one of the most emotional male R&B groups at the height of their success created a monolithic and sentimental hit which we haven’t seen the likes of since.

Puff Daddy & Faith Evans featuring 112 - I'll Be Missing You (1997)

Puff Daddy didn’t have a huge pedigree in sentimental songs when “I’ll Be Missing You”, a duet with Faith Evans featuring 112 came out in 1997. That being said, his life had been struck by a major tragedy in the sudden death of Chris Wallace – better known as the Notorious B.I.G. in 1996. As far as sentimentality goes, this one goes a little bit further than one might expect, stepping hard into saccharine territory. It was rare to see Hip-Hop guys be so straightforwardly emotional, especially at that time, so forgive him for being a little clumsy with it. I can appreciate the magnitude of the sentiment; this song goes all out. Diddy’s “Mo Money Mo Problems” is a great celebration of Biggie’s life, and stands as a better song twenty years later, so I recommend that if you’re looking to learn about Hip-Hop’s mindset after Biggie’s death

Bone Thugs 'n' Harmony - Tha Crossroads (1998)

I don’t think anyone was surprised to hear Bone Thugs ‘n’ Harmony put out such a direct, emotional ballad about death, but I don’t know how anyone could expect the fortitude with which they did it. "Tha Crossroads" hits the middle ground between sadness and melodrama, which is surprising considering how broad the subject matter is. This song isn’t an elegy for anyone; it’s an elegy for everyone. “Can somebody, anybody tell me why, we die, we die?” the song asks, a broad question, but one that almost all people will ask at some point. This has the desired effect for the most part, but that broad scope added to such a forceful chorus makes it work basically anywhere – I played "Tha Crossroads" on the way to the destruction of a building last year and it worked wonders. Also, yes, the video is a special sort of ridiculous 90’s R&B video, where the grim reaper leads a group of ghosts – including the ghost of Eazy-E – to the top of a mountain before a shirtless angel holding a baby. I think that adds to the charm.

Elton John - Candle in the Wind 1997 (1997)

This song wasn’t originally about Princess Diana, but it will be forever linked to her after Elton John’s performance of this song at her funeral. He originally released Candle in the Wind in 1987 but rewrote it after Diana’s death in 1997. It went to #1 in 23 different countries and is one of the highest selling singles in music history during a decade when album sales were more pronounced than singles were – well after the days of vinyl singles and a few years before digital downloads could take off. A classic, heartfelt song like this one had the power to do that, and it’s still a beautiful tribute to this day.

It wasn’t just Pop and Hip-Hop, either - Alternative rock had its own elegy songs, too like Alice in Chains’ “Would” about the death of Mother Love Bone singer, Andrew Wood, and R.E.M.’s “Let Me In” about the death of Nirvana frontman, Kurt Cobain. Something about the 1990s led musicians to think and sing about death on such a high-profile stage in a way that hadn’t been done the same way before, and has not been done since. So much emotion was dropped into these songs; it has helped them stay around in the public mindset ever since.