Sing About Me: Rappers Keeping The Art of Storytelling Alive

From Kendrick to Lupe, only the true greats can bring other characters to life through their rhymes.

You never know what to expect the first time you hear a new artist. Pressing play on an album is like showing up for a blind date, unable to predict what awaits, thrilled by the unknown. You reach the highest of highs when impressed and the lowest of lows when underwhelmed. 

I recently rediscovered that elation when I met DJ Booth Top Prospect Jay IDK at A3C. Before I heard any of his music he told me if I ever got a chance to hear his album, Subtrap, I needed to listen from beginning to end, instructions to ensure that I got the full experience. He was right. By the end of my first listen I was ready to play it again, the album is an experience that can only be truly appreciated when played in its entirety. Jay didn’t just make an excellent album, he executed a brilliant concept, one that truly feels fresh and inventive. Jay takes us into the trap but there’s no Versace being worn, Trap Queens cooking pies or yams being stored in his auntie’s basement. The trap he speaks of is too big to be told from one man’s eyes, so he tells stories based on the trap from multiple perspectives.

He tells the tales of a starving artists selling weed to make music, the greedy plug with dollar signs for pupils, the street hustler with a family that needs the block to survive, the fiends that are chasing their next hit, the college student using drugs to cope with the pressure of his future, and the man like many men before him that falls victim to the power of women. Jay doesn’t just narrate these characters, he becomes these characters – one man as the voice of many. It’s like listening to the circle of life told from the block, a jungle that thrives off greed, desperation, and addiction. By the end, you see how certain stories intersect; it's impeccable storytelling through and through. Storytelling is in the DNA of hip-hop, emcees have been using words to paint pictures since the Genesis, but Jay takes it a step further. So many rappers can tell their own stories but to truly inhabit someone else’s mind and body, that’s some advanced artistry. He’s far from the first, it’s not a common approach, and at times it’s done in a banal way, but when it’s executed with perfection, it’s hard not to be impressed.

The first time storytelling really caused my soul to stir was on Lupe Fiasco’s Food & Liquor. Track number 4, “He Say She Say,” is a simple song, but the way the Chicago veteran elegantly articulates the struggles of a single parent home from the mother’s perspective and then the fatherless son by just changing a few words is astounding. A masterpiece doesn’t have to be complex, simple can be equally as powerful. If you believe Genius, this song is the childhood story of Michael Young History, the character that awakens in a grave on song “The Cool.” Lupe has an uncanny ability to illustrate, he has the pen of a screenwriter, the rich details could easily be translated to the big screen. If these two songs are based in the same universe it’s an interesting parallel, a glimpse at his childhood and resurrection before diving into the depths of the character. He saves the much bigger story though for his sophomore album, The Cool.

Unlike Jay, Lupe didn’t dedicate the entire album to Michael Young History (MYH), throughout the 19 songs, Lu spreads the story out through four-and-a-half songs. I didn’t realize until browsing Rap Genius that the first verse of “Superstar” explains why Michael came back to life. It’s a little weird because Lupe juxtaposes himself trying to get into the club and MYH trying to get into heaven. The song switches between these two viewpoints. There’s a line from God that goes, “Go back, whatever you did you undo.” This is where he's rejected from both heaven and hell, reborn as a man with a fleshless right hand. Since the story lacks a linear narrative it's easy to get lost in the sauce. It’s also pretty slick how he slides such a critical part of the story into one of his most popular commercial singles. Before “Superstar” is the song “The Coolest,” prequel to “The Cool,” and the first time Lupe steps into the shoes of MYH. This masterpiece is also the first song that introduces the other characters intertwined in the story, The Game and The Streets. The story’s climax and MYH’s death is told on “The Die,” a frame by frame look at the feverish angst that was building up on his last living day. Lupe plays a friend that is telling MYH of what is being said in the streets and not to worry while Gemstones is the shooter that’s planning to take his life.

That explanation given doesn’t begin to do Lupe justice, The Cool saga could easily be translated into literature, the way he’s able to give so much story through so few records will always be something that I admire. Unfortunately, the story never got its true conclusion due to LUPend being shelved indefinitely. It’s like when your favorite show is canceled before its final season, a true hip-hop tragedy, but it will forever solidify Lupe’s place as one of rap’s greatest storytellers.

You can’t write about masters of modern storytelling without mentioning King Kunta. Kendrick is a true writer, able to observe and recite; this is a man that captured the spirit of a generation, documented the madness of his city and then the world. Kendrick is the kind of rapper you turn on and enter his universe, there are countless stories being told across his albums but there’s only one that truly feels like he transcended into that next echelon of storytellers, “Sing About Me/ I’m Dying Of Thirst.”

What makes this song so special? It comes after the extended version of “Swimming Pools” on the GKMC album, there’s a skit that depicts a shooting and the death of a friend. The first verse of “Sing About Me” is Kendrick rapping from the friend’s brother’s perspective. You hear Kendrick’s voice but it’s obvious that he’s completely immersed in this character, a gangbanger that is trapped in the cycle of violence and has found solace in this path, there’s a certain sincerity that tugs at your heart during the candid verse, you just can’t help but feel sorry for him. When he says, “If I die before your album drops” and then the sound of gunfire cuts him off, it’s like watching G-Baby die in Hardball all over again. In the second verse, Kendrick steps into the stilettos of Keisha’s sister, a woman that he wrote about on Section80, the previous album. The tone he uses for her is much more menacing, she’s outraged by Keisha’s Song, seeing the homage as unwanted and distasteful. I like how he’s able to give this unnamed woman so much life, the life of a prostitute that just buried her older sister and had to hear about the tragic story on a rap album. The eeriest part comes at the end, after she admits that a doctor has diagnosed her with some sickness that she continues to deny, breaking into a full blown rant, saying, “I’ll never fade away, I’ll never fade away” and after that, her voice slowly begins to fade. It’s chilling, simply chilling.



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Both stories are true, Kendrick has had multiple interviews saying that the two verses represent two people with polar opposite views on him and his music. One sees his music as a way of taking his story and shedding a positive light upon the tragedy, he wanted to be sung about. The other didn’t see it that way, she actually asked him not to sing about her on the album. For him to take those two encounters and write verses from their perspectives without their assistance is a testament to his skill as a writer. In the final verse Kendrick confronts them and himself, ultimately asking will the world sing about him when it’s all said and one. It’s a sad yet beautiful song. The kind that will be ranked at the top of his discography when it’s all said and done, and it’s his ability to truly inhabit another person’s point of view that makes the song a classic.

The Game is another Compton offspring that was able to turn his wild youth into some unforgettable hip-hop. One song that I always felt didn’t quite get its recognition is “Never Can Say Goodbye” from his third album, LAX. It’s a song that pays homage to the final day in the life of Tupac, Biggie, and Eazy-E. The Game does his best impression, trying to match the voices, cadences, and flows of the three legends. For a rapper known for being able to adapt to the styles of others, this shows that he can add a bit of depth to his imitation and makes for a pretty incredible song.

Fans of J. Cole know that his pen has jotted stories since the days of “Lights Please,” he has a knack of making the kind of music that feels like it's reflecting genuine human emotion. The best example of this has to be “Lost Ones,” from his debut album, Cole World: The Sideline Story. It’s a tender exchange between a young couple dealing with an unplanned pregnancy, the first verse from the man's perspective implying that abortion is the best way, but the song truly comes to life in the second verse, when the woman shares her feelings of betrayal. Cole really nails her passion, giving the listener both sides, a fictional story that is delivered in a way that feels very real.

This is just scratching the surface, hip-hop is littered with immaculate storytellers that can speak from the vantage point of someone other than themselves. What Eminem did with “Stan” is in a different class of artistry, a flawless diamond that’s perfect in every way. “I Gave You Power” by Nas is pure genius, a song told from the outlook of a gun, it takes a master wordsmith to even attempt such a record. With that said, it should come as no surprise that the heralded lyricist Pharoahe Monch rapped from the perspective of a bullet on “Damage.” Can’t forget about Joe Budden’s “Three Sides To A Story” and Jay Z’s “Meet The Parents.” There are also plenty of concept albums in hip-hop that have been dedicated to next level storytelling, for example, The Roots Undun, Flying Lotus You’re Dead, Sticky Fingaz Blacktrash: The Autobiography Of Kirk Jones, and of course Kool Keith’s Dr. Octagonecologyst.

Throughout the history of rap, you’ll find practitioners that truly pushed the envelope on storytelling, creating unforgettable characters that are able to touch a listener in a way that wouldn’t be possible if the rapper couldn’t come out of himself and speak from a new outlook. I see Jay IDK joining their ranks with Subtrap, an album that truly sets itself apart during a time where trap music feels the most copied and redundant.

God bless the storytellers that remind you of how amazing this art form truly is.


By Yoh, aka the Yohryteller, aka @Yoh31.

Art CreditTrysten Josiah HarnessCarrillo



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