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5 of the Saddest Rappers That You Should Be Listening To

Updated on January 9, 2020
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Ethan is a transgender male actively involved in his local LGBTQ+ community. He writes informative articles on his personal experiences.

Depending on what generation you grew up in has a huge impact on what you listen to. I was born in the 90s but grew up predominantly in the 00s. Some generations such as the 60s babies listened to more soft, feel-good rock, while 90s kids grew up listening to Backstreet Boys, Britney Spears, and N*Sync. Regardless of the generation, you grew up listening to, Rap and R 'n B have been popular genres for decades.

Starting in the 00s, there was a sudden shift in teen culture. Music became more open, more emotional. Why? Because we became more expressive. In the 00s "Emo" music, a Punk-Pop hybrid exploded. Suddenly there were Emo bands everywhere. Just like the 80s had their big hair and glam clothes; shaggy, black or neon hair and raccoon-tails became the "in" thing of the 00s.

We had bands such as Bring Me the Horizon, Silverstein, Alesana, and Pierce the Veil blended emotional lyrics with high-energy, heavy-riffed guitar licks. Blending Emo music into heavy metal creating genres like "Deathcore" and "Screamo."

Eventually, as the mid-2000s faded into the rear-view so too did the Emo and Scene fad. Bring me the Horizon, Sleeping with Sirens, and other Screamo bands reinvented themselves, and then we saw a new trend appear around approximately 2010-2012. Emo bands like Issues and Dance Gavin Dance became increasingly popular which started to blend Emo with Rap and R n B.

From around 2015 to 2017, we have seen a new fusion evolve from bands like these, Emo Rap. The "sadboys" as social media has labeled them. These "sadboys" have each left and are continuing to leave their mark in music culture. These 5 saddest rappers are what you should be listening to right now.

The "sadboys," as social media has labeled them. These "sadboys" have each left and are continuing to leave their mark in music culture

Lil Peep - Hellboy
Lil Peep - Hellboy

1) Lil Peep

Gustav "Gus" Ahr was born in 1996 in Allentown, Pennsylvania and raised in Long Island. He originally started releasing music on Soundcloud, and soon became popular after releasing mixtapes such as Hellboy.

His first album, Come Over When You're Sober, Pt. 1 peaked at 39 on the Billboard 200 chart and Come Over When You're Sober, Pt. 2, which dropped after his passing, debuted at number 4. His lyrics are emotionally driven and deep. They evoke a vivid picture of how he looked at love and even at life, which was depicted in some of his songs like Life is Beautiful.

One of the things that is so unique about Peep's music is that he used melodic, grunge-y guitar riffs as backing to his rap tracks. Earning him the nickname the "Kurt Cobain of Rap," as his music was game-changing for the Rap industry, and like Cobain, he met an early and unfortunate end to his life due to an overdose of Fentanyl-laced Xanax in late 2017.

If you like Rap and early-90s Rock, you are sure to love Lil Peep's music.

If you like Rap and early-90s Rock, you are sure to love Lil Peep's music.


2) XXXtentacion

XXXtentacion, whose real name was Jahseh Dwayne Ricardo Onfroy known as X to friends and family, is known as one of the most emotional rappers in history, he rapped about everything from a friend of his who committed suicide while visiting him to sex and drugs. Both him and Lil Peep were met with controversy over their drug abuse as well as X's violent past.

Unfortunately, X is also no longer with us, as he passed from gunshot wounds in June of 2018 which was less than a year after Lil Peep's tragic overdose.

He blended genres like Screamo, Punk, and Rap in his fast-paced flows. If you like Lil Uzi Vert, Trippie Redd, or faster paced rappers like Eminem and Logic and acoustic guitar, you should give XXXtentacion a listen.


He blended genres like Screamo, Punk, and Rap in his fast-paced flows.

3) Juice WRLD

Juice WRLD, Jarad Anthony Higgins, was born in December of 1998 and passed away of a seizure induced by substance impairment 21 years and 6 days later. He created one of the biggest followings in the Emo Rap industry. His album Goodbye & Good Riddance discussed difficult topics such as substance abuse, relationship problems, and suicide. He released his last album last year, Death Race for Love. Unfortunately, he will never see the full extent of the success of the album.

Juice WRLD blended Rap, Emo, and R 'n B in a unique way, his songs are relatable and expressive, and also discouraged substance abuse by rapping about his lifestyle even though it could be seen as the other way around. He did not condone it, yet it eventually took his life.

4) Lil Uzi Vert

Symere Woods, best known as Lil Uzi Vert, Uzi, and Uzi Vert is another pioneer in the Rap industry. Most of his songs discuss the emotional turbulence that he's experienced in different relationships that he has had. He is currently signed with Roc Nation and was formerly signed with Atlantic Records.

Unlike the other rappers that we have discussed so far, Uzi is still alive and well, making hits that blend rock and rap together to create a unique combination that "just works." If you like Marilyn Manson, you'll love Lil Uzi Vert.

5) Guccihighwaters

Guccihighwaters is a name that most people aren't familiar with. Guccihighwaters or Morgan, is an 20 year old Irish vocalist and producer. Now residing in New York, he is one of the most popular rappers/vocalists that has flown under the radar.

Morgan's music is deep and depressing. If you are wanting to listen to something that will break your heart and make you cry, you should listen to his music. His songs are powerful, and have a slower tempo than the prior 4 artists listed above. He sings and raps about suicide and relationships as well as explaining what it is like to fade into the background. If you're shy, you may be able to relate with his music.

Last Word

Tragedy has no doubt rocked the rap industry with the passing of three of these artists. I believe that we can learn a lot about their life prior to their death and keep them alive by promoting and listening to their music.Although they have passed, they no doubt left their mark as talented artists that we can connect to.

As Rap continues to evolve, my hope is that there is more suicide and drug awareness promoted in the music that we listen to. We can all learn a lesson from each of these artist's music and that is why you should give these 5 saddest rappers a listen.



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