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8 years have passed since the tragic loss of XXXTentacion, who was fatally shot during an armed robbery in Deerfield Park, Florida, in June 2018. He was just 20 years old.

Throughout his rapid ascent to fame, XXXTentacion — born Jahseh Onfroy — became a voice for millions of fans, standing out as a prominent figure in the SoundCloud rap movement. His music often revealed raw vulnerability, shedding light on his own struggles with mental health and battling depression.

X fully committed to his music career in 2016, sharing living space with fellow Florida rapper Denzel Curry. By early 2017, he broke into the mainstream with the re-release of his aggressive track *Look At Me!*, which gained massive traction on SoundCloud before expanding to other streaming platforms.

Although his musical talent was undeniable, XXXTentacion’s legacy is complex and controversial. He faced numerous legal troubles, including charges of domestic violence, assault, witness tampering, and robbery. At the time of his untimely death, he was dealing with 15 felony charges linked to an arrest in 2016.

This Friday (January 23) would have marked what would have been X’s 28th birthday. From brooding introspection to unbridled rage, his artistry exhibited a wide emotional range that hinted at boundless potential for his career in his twenties.

Below, we spotlight what we believe are 5 of XXXTentacion’s finest songs.

5. “Amy Winehouse”

“Amy Winehouse” is a hidden gem from a budding XXXTentacion, released on SoundCloud in 2015. The track carries a dark, ominous vibe with X unapologetically boasting about having an intimate encounter with a friend’s girlfriend.

His whispered, haunting delivery feels like it penetrates straight to the listener, accompanied by eerie piano keys that evoke the suspense of a horror film.

4. “SAD!”

“SAD!” stands as one of the most iconic records from X’s catalog, becoming his only top 10 hit while alive. In the week following his untimely death in June 2018, this heartfelt track soared to #1 on the Billboard Hot 100 as fans honored his legacy.

It became the first posthumous chart-topping single since The Notorious B.I.G.’s “Mo Money Mo Problems”. With production from John Cunningham, the song delves deep into X’s emotional struggles with heartbreak and depression, highlighted by the melancholic refrain: “Suicide if you ever try to let go, uh/ I’m sad, I know, yeah.”

3. “Vice City”

“Vice City” offers a glimpse into X’s early artistry and remains a beloved classic among his fans. This was the first song he shared on his SoundCloud in 2014 and later made its way to major streaming platforms eight years afterward.

At just 16, a young XXXTentacion discovered a free “Logic Type Beat” online, sped it up slightly, and turned it into an introspective masterpiece. Lyrics like “If you stated opinions, then bones would begin to shatter” showcase his unfiltered honesty and creative depth, even as a teenager.

2. “F**k Love” ft. Trippie Redd

“F**k Love”, featuring Trippie Redd, exemplifies the undeniable synergy between the two artists. This haunting exploration of a tumultuous love story is hailed as some of their best work together.

The track’s emotional intensity is further amplified by the bittersweet fact that X’s passing coincides with Trippie’s birthday. In 2023, the platinum-certified collaboration reached diamond status, posthumously securing X’s place in music history alongside his frequent collaborator.

1. “Look At Me!”

“Look At Me!” is an explosive anthem that forced its way into mainstream consciousness with unapologetic force. Released in 2015 and later adapted for streaming platforms in 2017, it marked X’s breakthrough moment, capturing the rebellious energy of a disenchanted youth while breaking through Florida’s local music boundaries to gain national attention.

The unfiltered aggression and rawness of the track earned it a spot on the Hot 100 and solidified its place as one of X’s defining works, showcasing his do-it-yourself ethos that resonated with millions.

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