More of The Greatest Hip-Hop Storytellers —Ever

At one point, Lil Wayne was considered by many young listeners to be the greatest rapper ever. While I don’t fall into that category, Wayne’s skills and star power at his peak were undeniable. In 2018, with the release of the long-anticipated, Tha Carter V, the New Orleans rapper reminded rap fans of his ability. The best example of his skill was on “Mona Lisa,” a song about the story of a woman who set up her boyfriend for a robbery.

Rhyme-for-rhyme, in terms of skill putting words together, Rakim is easily one of the greatest rappers of all time. So there should be no surprise that he is incredibly talented when it comes to storytelling. One of the best examples of his storytelling ability is “Mahogany,” a love song where the New York MC is describing his love of a woman through nutritional metaphors such as, “Each moment’s a mineral, poetry’s protein/ verse is a vitamin, effects like codeine.” That’s just incredible wordplay for an era, not just the 1990s.

It’s crazy how someone as influential and accomplished as KRS-One can be underrated, but he’s one of the greatest to ever touch a mic. While he’s known for being a “Teacha” on the mic, n the 1987 track, “9mm Goes Bang,” from Boogie Down Productions, KRS tells a story about his 9mm pistol. You should listen to the track to appreciate its brilliance, but it essentially is about KRS always keeping his piece by his side.

The first lady of DMX’s Ruff Ryder’s crew, Eve is a talented rapper who did not quite get her credit as a proficient storyteller and lyricist. On her 1999 debut project, Let There Be Eve...Ruff Ryders’ First Lady, on the track “Love Is Blind,” Eve opens up as a vulnerable person, who sees her friend experience an abusive relationship with her boyfriend.

Yeah everyone knows Ice-T as Fin on the long-running television show Law & Order: SVU. But what put him on the map as a rapper and entertainer is the 1987 track “6 N’ the Mornin.” Along with being a tale of a gangster in the streets of Los Angeles who is running from cops, shooting dice with his friends and hanging with his girl, this song also increased the prominence of “Gangsta Rap.”

The greatest band in the history of music always does a great job of getting across heavy and thorough messages, whether it’s on their 2014 album, ...And Then You Shoot Your Cousin or their classic 1999 album, Things Fall Apart. The 1999 track “You Got Me,” is about a relationship that deteriorates over time due to a lack of trust. Black Thought and Eve both come through with incredible verses to cap off this classic track.

Slick Rick is all about storytelling. His debut album, The Great Adventures of Slick Rick, is full of them, most notably “Children’s Story,” which initially sounds like a lovely bedtime story for children but turns into a tale about a kid who follows his friend into a life of crime. While his debut album is filled with incredible stories, another great storytelling song is “The Moment I Feared.”

No surprises here. Nas is universally known as one of the greatest lyricists in the history of rap and also one of its best storytellers. While he has a multitude of songs where he raps amazing stories such as “Shootouts,” “I Gave You Power,” and “The Set Up,” my favorite storytelling song from Nas is “One Love.” Where Nas raps a letter he wrote to his friend who is in prison. Famously, the third verse in the song describes a conversation he has with a young kid; that verse was later depicted in a scene in the 1998 movie Belly.

Hov’s storytelling has changed over the years. On “Friend or Foe,” from Jay-Z’s debut album Reasonable Debut, listeners can hear Jay rap about being a drug dealer and a stranger who he believes is planning to take over his “business.” “Meet the Parents” from Blueprint 2 sees Jay-Z tell the descriptive story of a family’s decline with the moral being to always be there for your kids no matter what.

K. Dot is one of the younger names on this list and is already considered one of the best rappers and storytellers in the history of rap. His debut studio album, good kid, m.A.A.d city, is a story in itself, but also includes a multitude of smaller stories that fit into the overarching theme of that album. Some of those songs include, “The Art of Peer Pressure” and “Sing About Me, I’m Dying of Thirst.” But one of his best is “DUCKWORTH,” where he tells the story of how his father met Anthony “Top Dawg” Tiffith, the man who founded Top Dawg Entertainment (TDE), the label Kendrick eventually signed to.

Known as one of the most ruthless and hardest MCs in the mid-90s, Cube was also one of the most vivid rappers during his heyday. Tracks like “My Summer Vacation” stand out. But he’s most known for the classic track “It Was A Good Day,” where Cube just enjoys a stress-free day where he plays basketball, wins a dice game and goes past the police and rival gangs without incident.

He did it as a member of Geto Boys, and he also did it as a solo artist. Scarface just has a knack for telling dark and descriptive stories in his music and has a plethora of tracks to choose from. One of those tracks that best displays his storytelling ability is “I Seen a Man Die,” which follows the story of a man trapped in a cycle of violence, regret and loss. But, his most famous storytelling song is by far “My Mind Is Playing Tricks On Me.” In the song, Face describes how exhausting it can be to live a life as a gangster dealing with PTSD, loneliness and thoughts of suicide.

For many, Notorious B.I.G. is the greatest rapper of all time. But for me, he’s also one of the best storytellers. Some of his most famous storytelling songs are “Warning,” “Niggas Bleed” and “I Got a Story to Tell.” But my favorite track that displays Biggie’s storytelling skills is “Gimme the Loot”, which sees Big play the role of an OG and a young guy who plans on robbing people in his neighborhood. It’s a pretty violent song, but it nonetheless displays his skills in an amazing way.

One of the most interesting, influential and beloved rappers to ever live, 2pac was known for being multi-layered in his music. He made some of the most hard-hitting songs ever in the 90s, while also writing some of the most emotional and heartfelt tracks of the decade. Most of those heartfelt songs included some sort of storytelling, most notably “I Ain’t Mad at Cha” and “Dear Mama.” But, his most famous storytelling track is “Brenda’s Got a Baby,” which tells the incredible story of an abused pregnant preteen. Throughout the track, Pac addresses pregnancy, abortion, welfare and the Black family structure.

Yes I know, Outkast counts as two artists, but together as a duo, they made such incredible and beautiful music. Some of their most memorable songs are written about descriptive and interesting tales of being a “pimp.” Their third album, Aquemini, included a multitude of those types of tracks including “Da Art of Storytellin’, Pt. 1” and “SpottieOttieDopaliscious.” The former track hears Big Boi on the first verse rapping about cheating on his baby mama with Suzy Screw. The second track hears Andre rap about growing up with Suzy’s friend Sasha and talking about what they want to be when they grow up. The ending of track ultimately ends much sadder than it began.

There are so many dope MCs in Wu-Tang Clan, but I had to single out Ghostface Killah, who’s the best and most consistent rapper in the group. One of the best examples of Ghostface’s storytelling is on Wu-Tang’s sophomore album, Wu-Tang Forever, on the track “The MGM.” You can hear Ghostface and his best friend, Raekwon, rap about watching a Julio Cesar Chavez fight at the MGM Grand in Las Vegas. Another track that showcases Ghostfaces’ skills is the 2001 track “Maxine.”

Unlike some of the other MCs on this list, some of J. Cole’s best examples of his storytelling skills are in light-hearted songs. Most famously, “Wet Dreamz,” which tells the innocent story of J. Cole losing his virginity to a girl. In the story, he tries to play it cool acting like he’s done this before, when it reality, he hasn’t.

Unfortunately, Big L didn’t live long enough to have an extensive list of storytelling songs, but in his short career, he made the most of it. The two best tracks that showed off his skills are “The Heist” and “Casualties of a Dice Game.” The latter takes inspiration from Notorious B.I.G. and tells an interesting and descriptive story of robbery and vengeance.

Mos Def, now known as Yasiin Bey, is one of the more underrated MCs in the history of rap. “Ms. Fat Booty,” was the lead single from his debut album, Black on Both Sides. It is not only his most popular track to date, but also one of the best examples of his storytelling ability. The track tells the tale of Def’s relationship with a girl with an “ass so fat that you could see it from the front.”

Y’all may have forgotten, but before Common was a successful actor, he was a thoughtful and poetic MC. One of the most unique storytelling tracks ever, “I Used to Love H.E.R.” sounds like the Chicago rapper is rapping about a girl who has lost her way and moves to the West Coast to hang out with a crew of gangsters. But, by the end of the song, it turns out he’s been rapping about hip-hop itself the entire time.

Public Enemy has so many hard-hitting songs filled with powerful political messages throughout their impressive catalog. On some of their tracks, they infused their politically charged cynicism in some incredible storytelling songs such as “Black Steel In The Hour Of Chaos.” In the song, Chuck D plays the role of a man who refuses to enter the military to fight for a country he doesn’t believe in. As a result, he’s taken to prison. Eventually, he breaks out of prison along with a multitude of other inmates. While the original track ends with Chuck and his friends on the run, the music video ends with Chuck D getting executed.

I ain’t forget about New York rap legend Kool G Rap. While his stories weren’t always happy or positive, they were always just as detailed. My favorite example of that is on “III Street Blues,” where the mafioso rapper spits about a bartender that needs to pay back his debts. He does the same thing on “Train Robbery” where he raps about committing a robbery along with his friends.