A key ability for a rapper is how to spin a yarn. Historically, the best rappers knew how to weave a tale that would grip listeners and captivate their imaginations. So I’ve compiled a list of storytelling raps that encompass creative writing, plot twists, vivid imagery, literary devices, and are all around dope. Here are some of the most evocative storytelling raps that will make your hair stand on end.

D Rrugs – Cam’ron

Cam’ron doesn’t get the credit he deserves as a wordsmith. This song has him tell the story of many kids in the ghetto who become affected by the dangers of drugs. The character of D Rugs is personified and made into Cam’ron’s step-father. Using the sample of Curtis Mayfield’s “I’m Your Pusherman”, Cam’ron builds on stories of substance abuse, using wordplay for each drug, to explain how each drugs is consumed on the first verse. Then Cam’ron delineates how he came to be a drug dealer on the block. D Rrugs evolves from being a pimp exploiting his mother, to being Cam’ron’s greatest benefactor.

December 4th – Jay-Z

What makes this song great is its autobiographic nature. The song is intercut with narration from his mother as they paint a picture of what it was like for a young Shawn Carter while also being a curtain call for Jay’s career — at least at the time of its release. “December 4th” named after his birthdate, draws a picture of how a boy became the man known as Jay-Z. The story is incredible, in the sense, of how short of a time span, Jay is able to detail the importance of music, the loss of his father, and the beginning of his rap career.

Subtle Art of the Breakup Song – Cage Kennylz

One of the most harrowing stories on this list. On this track, Cage details the story of how he accidentally killed his girlfriend in a car accident whilst being high on Ketamine – on her birthday no less. The track has foreshadowing as Cage makes several mentions of the rain throughout the song, that eventually makes him lose control of the car. The rain and delayed response time from being on Ketamine end up making a deadly combination.  Removed from his body, he sees the events unfold. The song is exceptionally dark as he tries to bleed out after crashing on the freeway looking at what he has done. 

Warning – Notorious B.I.G

An epic tale told by the Notorious B.I.G, of how greed has gotten his rivals into a frenzy over his wealth. Biggie plays himself as well as the role of Pop on the phone, a role originally reserved for Craig Mack. What makes this song great is Biggie’s vivid descriptions. You can picture Biggie being armed to the teeth after receiving a troubling phone call. The paranoia is quite convincing. Biggie questions if friends have turned into foes and is ready for war. It comically ends with the perpetrators having a “red dot”on their heads before being blown away by Biggie’s heavy artillery. 

Duckworth – Kendrick Lamar

An amazing story on the pulitzer prize winning, DAMN album. On this song, Kendrick tells the tale of Anthony and Ducky. Anthony is the street wise kid who grew up in the projects hustling and selling crack, while Ducky is a KFC worker who had moved from the Southside Projects to Compton who is hip to the game. Anthony was planning to rob the KFC but refrained from doing so, as Ducky would always give him extra chicken and biscuits and liked him. The irony of the song is revealed at the end where Kendrick explains that Ducky is actually Kendrick’s father and Anthony is the real name of TDE CEO Top Dawg.

Dance with the Devil – Immortal Technique

An underground classic. This song extrapolates the repercussions of living the gang life. Following the story of Billy William Jacobs and how he further descends into wickedness. While the story of Billy William Jacobs is an urban legend, it serves as a metaphor for the damage done to black and latino communities through gang and drug violence. Adding to the eerie feeling of the song is the sample, “Theme from Love Story” by Henry Mancini as Immortal Technique describes Billy’s corruption. The supposed dance with the devil is how hustling can be a slippery slope, and the twist is M. Night Shyamalan worthy.

Da Art of Storytelling Pt.1 – Outkast

On this song, Outkast regales us with the story of  two different women, Susie Skrew and Sasha Thumper. Big Boi’s verse delves in the topic of promiscuity, discussing a known “hoodrat” named Susie Skrew. But Andre’s verse is the real star here. Andre’s verse about Sasha Thumper is a coming of age story that ends in tragedy. Andre’s vivid descriptions of dancing under street lamps help paint a picture of an intelligent young woman who ends up making bad choices and faces an untimely demise as a result. Andre implements a real sense of pathos, giving the song its poignancy.

Mind Playing Tricks On Me – Geto Boys

A song about post traumatic stress. Scarface’s verse was years ahead of its time. While Bushwick Bill’s verse helped pioneer the genre of horrorcore.

Scarface really shines on the song. Like Biggie’s “Warning”, Scarface gives vivid depictions of paranoia as a result of a life of violence catching up to him. Face feels like the walls are closing in on him as he sees his double in the shadows. The fantastical elements of the song also help create a sense of spookiness. From the claustrophobic feeling of Scarface’s verses to Bushwick’s unreliable narration, this song set a precedent for many future storytelling raps after.

Uncommon Valor: A Vietnam Story – Jedi Mind Tricks FT. R.A the Rugged Man

The only song with a feature on the list. While Vinnie Paz’s verse rapping from the perspective of a soldier in the midst of a Vietnam battlefield is quite well-executed, detailing the historical and social context of the Vietnam War, it’s R.A’s verse that will have listeners completely in awe. R.A the Rugged Man’s verse is him rapping from the perspective of his father SGT. John Andrew Thorburn, who really served in the Vietnam War. The personal nature and the mile-a-minute flow while diving into the psychology of a Vietnam War soldier and it detailing the after effects of PTSD, the damage of Agent Orange on the sergeant’s kids make this song incredible as a piece of art.

Rewind – Nasir “Nas” Jones

Not every rapper has been gifted with storytelling abilities. To engage listeners in a story whether fictional or not without them losing interesting is a great skill for a rapper to have in their repetoire. It’s quite difficult to master. Even harder is to have the ability to make a story make sense to an audience when told in reverse. “Rewind” is the song equivalent of Memento. Nas’ storytelling ability here is incredible as he paints a vivid picture in a logical order backwards. Even some of the dialogue is backwards too which would make for a confusing song from a lesser rapper.

Honorable Mentions:

Pigeon by Cannibal Ox

One of the more abstract storytelling songs, Cannibal Ox contrasts the life of a pigeon to those in the ‘hood. It works quite well as the comparisons aren’t obvious at first but then touches on various social issues including: food deserts, socioeconomics, and gang violence. “Pigeon” provides a bird’s eye view of life in the ghetto.

Kenji by Fort Minor (Mike Shinoda of Linkin Park)

Kenji follows the story of Ken, who was a Japanese immigrant storeowner living in Los Angeles who had his and his family’s life upended after the attack on Pearl Harbour. Kenji’s family then become prisoners of war living in internment camps in America. Hanging on to hope, Kenji becomes a gardener in the camp and gives fruits and vegetables to the soldiers. Eventually, he and his family are released and able to return home, only to see their house vandalized. Thanks to Mike Shinoda’s effective storytelling, you really feel for them. The song serves as a reminder of the pernicious effects of xenophobia.

The Gates by Cunninlynguists

A Piece of Strange is Cunninlynguists’ Magnum Opus. It’s gospel bluesy raps are a heady trip for southern hip hop fans. “The Gates” stands out as one of the more conceptual tracks with Tonedeff rapping from the perspective of a firefighter at the pearly gates.

In Her Music Box by Atmosphere

Almost any song off of Atmosphere’s When Life Gives You Lemons could have made this list truthfully, as its cast of characters that are downtrodden feel so real. But to me “In Her Music Box” stands out as its most effective and serves as the perfect album closer. The song is told from the perspective of a drug dealer’s baby girl. It’s infectious hook, and music box instrumental service the song really well. The music box takes on multiple meanings, from the imagery of a little girl’s ballerina music box but also the car itself that has become a music box itself.

Do you agree with our list? What’s another song you think we should’ve included?