The 5 Best Storytelling Rap Songs From The '90s

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From Biggie's "I Got A Story To Tell" to Ice Cube's "Today Was a Good Day".

Storytelling is the second oldest profession, after prostitution. As the oral tradition evolved, it reached new heights in '90s hip hop, an era that place an emphasis on lyricism -- ideally #bars not for the sake of #bars, but #bars for the sake of humor, drama, or social critique.

Obviously, tough decisions were made as we whittled this list down to five. Do you agree with our choices? Check out our honorable mentions below and click through the gallery for the top five storytelling rap songs of the '90s.

Honorable Mention

Geto Boys - “Mind Playing Tricks On Me”
Jay Z - “Friend or Foe”
Mobb Deep - “More Trife Life”
Notorious B.I.G.  - “Niggas Bleed”
Notorious B.I.G. - “Warning”
Organized Konfusion - “Stray Bullets”
Outkast - "Da Art of Storytellin' (Pt 1)"
Outkast - “SpottieOttieDopaliscious”
The Roots f/ Erykah Badu - "You Got Me"
Snoop Dogg - “Murder Was The Case”


Notorious B.I.G. - “I Got A Story To Tell” (1997)

The 5 Best Storytelling Rap Songs From The '90s

Notorious B.I.G. - “I Got A Story To Tell” (1997) 

Biggie's natural brevity, wit, and flow make him maybe the greatest storyteller in the history of hip hop. In his magnum opus "I Got A Story Tell," he's doing the horizontal hustle with the girlfriend of a player on the Knicks, who, according to Fat Joe, os the late Anthony Mason. To add insult to injury, they're copulating in the player's bed. They finish their business -- then suddenly, they hear a call from downstairs. "Honey, I'm home!"

As he wonders how to make his escape, Biggie devises a plan most most devious. To cover his tracks, he ties up the girl and stages a robbery. In the end, he not only has cuckolded this man, but robbed him of a Prada bag full of cash. He takes off two words - "I'm gone!" - and heads to tell his homies on the block what had just happened.

Quotable Lyrics

The shit she kicked, all the shit's legit
She get dick from a player off the New York Knicks
Nigga tricked ridiculous, the shit was plush
She's stressing me to fuck, like she was in a rush
We fucked in his bed, quite dangerous
I'm in his ass while he playing against the Utah Jazz

Warren G & Nate Dogg - “Regulate” (1994)

The 5 Best Storytelling Rap Songs From The '90s

"Regulate" is told from two perspectives: Warren G, who is getting robbed at a dice game, and Nate Dogg, who is looking for Warren but distracted by a car full or females. Ultimately, Nate arrives on the scene and lets his "gat explode." They peel off into the night with females in tow and head for the Eastside for a long night of hot sex.

REGULATOOOORS!!!!

Quotable Lyrics

[Warren G]
It was a clear black night, a clear white moon
Warren G was on the streets, tryin' to consume
Some skirts for the eve, so I can get some phones
Rollin' in my ride, chillin' all alone

[Nate Dogg]
Just hit the eastside of the LBC

On a mission tryna find Mr. Warren G
Seen a car full of girls, ain't no need to tweak
All you skirts know what's up with 213

Tupac - “Brenda’s Got A Baby” (1991)

The 5 Best Storytelling Rap Songs From The '90s

No artist has ever produced a better debut single than "Brenda's Got a Baby," a story of a 12-year-old girl who gets pregnant by her cousin. Here's what Tupac said about the song in a 1997 interview with the New Yorker:

"When this song came out, no male rappers at all anywhere were talking about problems that females were having, number one. Number two, it talked about child molestation, it talked about families taking advantages of families, it talked about the effects of poverty, it talked about how one person’s problems can affect a whole community of people. It talked about how the innocent are the ones that get hurt. It talked about drugs, the abuse of drugs, broken families…how she couldn’t leave the baby, you know, the bond that a mother has with her baby and how…women need to be able to make a choice.”

Quotable Lyrics

He left her and she had the baby solo
She had it on the bathroom floor and didn't know so
She didn't know, what to throw away and what to keep
She wrapped the baby up and threw him in a trash heap
I guess she thought she'd get away, wouldn't hear the cries
She didn't realize how much the little baby had her eyes
Now the baby's in the trash heap bawling
Momma can't help her, but it hurts to hear her calling

Wu-Tang Clan - “Impossible” (1997)

The 5 Best Storytelling Rap Songs From The '90s

"Impossible" is about two things: the ancient wisdom of the Five Percenters, and the corrosive impact of gun violence on black communities. In Ghostface Killah's unforgettable third verse, he arrives on the scene right after his dear friend Jamie has been shot. Jamie has a young daughter; Ghost begs him, "Don't go!" 

In the end, paramedics arrive and Jamie is pronounced dead. RZA called Ghost's verse the greatest Wu-Tang verse of all-time and The Source awarded it Verse of the Year.

Quotable Lyrics

Call an ambulance, Jamie been shot, word to Kimmy
Don't go son, nigga you my motherfucking heart
Stay still son, don't move, just think about Keeba
She'll be three in January, your young God needs ya
The ambulance is taking too long
Everybody get the fuck back, excuse me bitch, gimme your jack
One, seven one eight, nine one one, low battery, damn
Blood comin out his mouth, he bleedin badly

Ice Cube - “It Was A Good Day” (1993)

The 5 Best Storytelling Rap Songs From The '90s

In his legendary ESPY speech, Jimmy Valvano said that to have a good day, you must laugh, think, and cry. In Ice Cube's "It Was a Good Day", he fucked, drank, won money, didn't get roughed up by the cops or a rival gang, and ate a burger. To each his own, I guess.

Quotable Lyrics

Drove to the pad and hit the showers
Didn't even get no static from the cowards
Cause just yesterday them fools tried to blast me
Saw the police and they rolled right past me
No flexing, didn't even look in a nigga's direction
As I ran the intersection
Went to Short Dog's house, they was watching "Yo! MTV Raps"
What's the haps on the craps?

About The Author
<b>Staff Writer</b> <!--BR--> <strong>About:</strong> President of the Detlef Schrempf fan club. <strong>Favorite Hip Hop Artists:</strong> Outkast, Anderson .Paak, Young Thug, Danny Brown, J Dilla, Vince Staples, Freddie Gibbs
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