7 of the Best Storytelling Rappers of All Time

Jermaine Cole took the rap world by storm with his debut 2011 single, Workout. The single recounted the ups and downs of a modern "situationship," with Cole recounting how he liked a woman but couldn’t quite commit to her. The single would serve as the catalyst for many of Cole’s relatable and nostalgic singles.

Wet Dreams perfectly summarizes the experience of the hormonal rage of a young teenage boy and the nerves associated with having sex for the first time. Cole’s lyrics are also often praised for tackling social and economic issues through distinct and clever wording which is part of what catapulted him to be one of this generation's favorite rappers.

One of the OG rappers, Slick Rick introduced music storytelling with his hit single, Children’s Story. Through a catchy beat and clever lyricism, the rapper recounts the story of a young teenager who takes the wrong path by robbing and mugging people. While fictional, the song tackled a serious issue, as in the late 80s, youth crimes were at an all-time high.

Rick also went on to make more story-based singles like Teenage Love, which talks an adolescent through the trials and tribulations of young love. Children’s Story was eventually turned into a real published children’s book, which further highlighted the rapper's storytelling skills.

This Queens based hip-hop group serves as an iconic part in the hip-hop community. Known for introducing an alternative hip-hop blend with jazz, their singles like Electric Relaxation and Award Tour gave listeners an inside look into the group's personal lives — whether it was chasing girls in New York City or the love and appreciate they recieved while on tour. The group was also praised for keeping their lyrics clean and tasteful.

Mentioning hip-hop without mentioning the notorious B.I.G. should be considered a cardinal sin. Hearing a Biggie song instantly transports you to 1990s Bedford Stuyvesant, which was filled with bright yellow taxis and the sounds of roaring trains.

While the rapper’s fame was at the height of the East Coast/West Coast war, it never changed the fact that many related to his lyrics. Whether it was when the rapper talked about struggling or arguing with his landlord about heat, or never having enough money (Mo’ Money, Mo’ Problems) the lyrics remained a part of Brooklyn and hip-hop history.

Kendrick Lamar’s debut album Good Kid, Maad City serves as a foolproof version of lyrical storytelling. Sprinkled with verbal anecdotes, the album tells a story with each track. Lamar recounts struggling with alcoholism in his family, and the territorial battles of southern California. A nimble mix of jazz sounds infused with hard hip-hop helps qualify the rapper as one of the best lyricists of the generation.

Tech N9ne is one of the rappers who helped bring underground rap to light. Many may remember his iconic cypher from the BET Hip Hop awards and the occasional song appearance in popular video games. Worldwide Choppers follows him as he finds other talents across the midwest while Am I A Psycho allows a peek into the feelings the musical lifestyle can bring.

Big Boi and Andre 3000 took the rap world by storm when they formed Outkast. Between six studio albums and 20 million record sales, the duo is known for their canny and gifted use of lyrics. The International Players Anthem provided an inside look into the duos struggles with the women in their lives, while Hey Ya! examined the state of relationships in the 2000s.

While the chorus and hook were upbeat and easy to dance too, 3000 states that it ponders on whether they want to stay in the relationship and how most people stay because that's what they’ve been told.

(But does she really wanna // But can't stand to see me walk out the door?// Don't try to fight the feeling //'Cause the thought alone is killing me right now // Thank God for Mom and Dad // For sticking two together 'cause we don't know how)