1. Slick Rick – Children’s Story (1988)

“This ain’t funny so don’t ya dare laugh / Just another case about the wrong path / Straight ‘n narrow or yo’ soul gets cast…” 

Slick Rick is known as one of the greatest rapping storytellers of all time. This song cemented that notion. It was released before the era of gangsta rappers and the idolizing of the guns, money, and drugs. With the Zulu Nation and Hip Hop’s roots still holding sway over rap culture, this song followed the more positive message of rap. It’s a message from an era far gone, where tales of gangsta lifestyle still end with the bad guy losing because souls “gets cast.”

2. Aesop Rock – No Regrets (2001)

“Look, I’ve never had a dream in my life / Because a dream is what you wanna do, but still haven’t pursued / I knew what I wanted and did it till it was done / So I’ve been the dream that I wanted to be since day one!”

I used No Regrets to teach my former junior high students about rap beyond the radio. Every year, first week of school, I played this for my students to teach them that in order to achieve a dream, it takes hard work and denying those attempting to deter you. Lucy’s work ethic is a little more intense and focused than most and is definitely one end of the focused-in spectrum, but man do I love it when she ignores all those hatin’ ass neighbors and kids.

3. Yasiin Bey (Mos Def) - Ms. Fat Booty (1998)

“I tried to play it low key but couldn’t keep it down / Asked her to dance and she was like, yo I’m leaving now…”

“I’m about to murk, I say peace to the family / She hop up like, how you gon’ leave before you dance with me”

These four bars foreshadow the conclusion of this story. Mos diggity Def is getting played by Sharice. Despite their long relationship, it was destined to end tragically. And how does it end but with Mos being dissed for another chick. Gotta watch out for those chicks with an “ass so fat so you can see it from the front.”

4. Notorious B.I.G. - I Got a Story to Tell (1997)

“She’s stressin me to f**k, like she was in a rush / We f**ked in his bed, quite dangerous”

It came out recently that this song is actually a true story. Fact #2 is that the New York Knicks player B.I.G. robs is none other than badass, mean mutha-effer Anthony Mason. Fact #3 is that my friends and I who watched basketball religiously used to think Anthony Mason’s team would beat the crap out of people in basketball and then go a rob a liquor store. They were seriously that tough. Turns out not as tough as a quick-thinking Biggie. New York must’ve been a tough place to grow up.

5. The Coup – Fat Cats, Bigga Fish (1994)

“That’s when I stepped back some to contemplate what few know / Sat down, wrestled with my thoughts like a sumo / Ain’t no one player that could beat this lunacy / Ain’t no hustler on the street could do a whole community / This is how deep shit can get / It reads “macaroni” on my birth certificate / “Puddin’-Tane” is my middle name, but I can’t hang / I’m getting hustled only knowing half the game…”

I don’t know if hustlers are listening or have ever heard this song, but if not, they should. This beat is crazy dope. Listen beyond the beat and this story is incredible. Boots Riley flexes why he’s one of the dopest lyricists never given his due. For most the song he is talking about why he is a “hustla for real.” He uses his game to get a free meal and his other skills to pick pockets a “fat cat.” However, after being allowed entrance into a party for rich CEO’s and other business owners – who are discussing, openly in front of the wait staff, their “hustla” skills of being able to buy elections, gentrify low income communities and manipulate the media, all while gaining the help of Jesse Jackson – he learns how he’s not as much of a hustler as he thought he was. Rappers should consider themselves lucky to learn this lesson.

6. Binary Star (One Be Lo) - Glen Close (1999)

“Coulda said “I’ll see ya later” but I stayed to child support her / I didn’t love the baby’s mother / Now she’s colder cuz I told her

One Be Lo takes storytelling one-step further with this song by doing that’s always made them stand out in my mind. They switch the beat up mid-song immediately changing the mood. Here, they employ the technique masterfully by switching it at the moment One Be Lo begins detailing that “when trouble started” between him, his ex and his ex’s mother (who might or might not have put something in her spaghetti to kill the rapper). In the end, One Be Lo’s life is spared.  His true love, however, is not.  The woman he left his ex-girlfriend for, that made the ex all crazy, takes it out on the rappers new chick. Which again exemplifies there is nothing as dangerous as a woman scorned.

7. Cage – Too Heavy For Cherubs (2005)

“Erratic then gone, I go from manic to calm / Watching the yellow liquid dripping back out of his arm / No automatic alarm sounded / Trying to wrap my six-year-old brain around it / Went in his pockets took his money and couldn’t count it…”

Like a few other songs mentioned here, I hope this song is a complete work of fiction. Cage’s dad, who is an ex-military heroin addict, asks a 6-year-old Cage to tie a plastic cord around Pop’s arm. This has to be one of the most terrible stories I’ve ever heard. But in the short time frame I spent learning about the juvenile court system in Arizona, I know reality is often times worst than fiction. Cage’s ability to provide realistic imagery makes this track often hard to stomach. In this song, I am reminded that Hip Hop paints a picture of a world that is dangerous and not pretty. KRS-One didn’t call it the ghetto’s Reading Rainbow, he called it the ghetto’s CNN.

8. Jedi Mind Tricks ft. R.A. The Rugged Man – Uncommon Valor: A Vietnam Story (2006)

I should just post The Rugged Man’s entire verse but I’m not. Please do yourself a favor and go to http://rapgenius.com/Ra-the-rugged-man-uncommon-valor-lyrics to read R.A. The Rugged Man’s lyrics for this joint.

R.A. The Rugged Man is a master lyricist who has never received the attention he deserves. Every record he’s ever made has been dope. In Uncommon Valor, he manages to explain (with a rapid fire, multiple rhymes in one bar-delivery) one man’s experience in Vietnam and after. The story is better or as good as every Vietnam story ever made. I especially love the line that was a common propaganda type refrain during the war how it really wasn’t a war, it was a “military conflict.” What’s the difference??? Do yourself a favor, listen to the song and read the lyrics right now….like right, right now.

9. Nas – I Gave You Power (1996)

“Always I’m in some shit / My abdomen is the clip, the barrel is my dick uncircumcised / Pull my skin back and cock me / I bust off when they unlock me / Results of what happens to niggas shock me…” 

Years after Organized Konfusion’s Stray Bullet came out, Nas invokes the metaphor of him being a gun. Nas introduces a concept that I personally believe was true – a gun with a conscience. “Tired of murdering and not being cleaned,” the gun ultimately decides to not function during a standoff. The result is his owner is shot by a “newer version” of him. A gun or new jack – one who hasn’t seen the bloodshed the other has experienced – ultimately kills the owner. The lyrics are clever and poignant, however the result is inaccurate because really guns don’t kill people, people kill people.

10. Brother Ali – Dorian (2003)

“I said somebody need to beat your ass / And then teach your ass, and I’m sorry I can only do half…” 

Brother Ali, a man whose lyrics have always illustrated him as a moralistic and idealistic man, learns in this song that you can’t save those who don’t wish to be saved. Like he states, he does beat the shit out of Dorian only to learn that Dorian’s wife continues to enable Dorian’s domestic violence against her. Thus Dorian never learns it’s not okay to hit a woman.

11. Common – I Used to Love H.E.R. (1994)

(Spoiler Alert – the following analysis of this song gives away the ending – and if you get mad at that, that is your fault. You’ve had your entire life to hear this classic and by not doing so, well sorry. At least take solace knowing it’s the type of song that gets better with each listen and that helps Hip Hop heads learn more about the history of the culture.)

“But I’mma  take her back hoping that the shit stop / Cause who I’m talking bout y’all is Hip Hop”

Listen, I could go on and on about this song. The man wraps Hip Hop into a metaphor about a girl. I can relate because my love for women is equaled by my love for Hip Hop. I could discuss how it’s a story about Hip Hop’s evolution or how it how very intelligently packages Hip Hop’s history into three verses. I could discuss how it started one of the best rap beef’s of all time between Common and Ice Cube.[2]

Instead, I’m going to say that Common had a point to make. But the issue shouldn’t have been directed towards the artists making music. They were merely rapping about their environment. As Questlove says in his book, “The younger me may have sat up all night with band mates raging against Puffy or DMX or whoever, but the fact is that they were never the problem. The problem was that someone in the corporate chain of command felt that there was a need to play those songs fourteen times a day to eliminate alternatives.” Now it doesn’t even matter – Cube and Common starred in a horrible movie together, but made millions doing it, and recorded a record for the soundtrack. Once again proving, money changes everything.

12. Ugly Ducklings – Journey To Anywhere (2001)

“Who can maneuver on Chutes and Ladders to a make believe land?”

The message here – good old fashioned fun, imagery, metaphor, symbolism, and simile. Honestly, I love the original version of this song much better. In its raw form it appeared on a compilation for Los Angeles school’s music programs.

This overproduced version that appears on the album of the same name overdubs the f**k out of a great song. It is all good though because the content remains and that is what makes this song a beautiful journey through 80’s and 90’s toys, books, games, shows, cartoons, and other pop culture. The make

The make believe land created by California rappers Dizzy Dustin and Andy Kat name check Pat Sajak, Glass Joe, the Groovy Ghoulies, and Pippi Longstocking. I love it because of the nostalgia associated with these characters and my own youth. It takes all my favorite things from my childhood and throws them together into an imaginative world that sees things like Captain Hook making shish kabobs with Etch a Sketch knobs and Schleprock from the Flintstones fighting with the Rock Em Sock Em Robots.

13. Eyedea & Abilities – Birth Of A Fish (2001)

“I’ve always lived inside this glass box that reminds him of his head / It just goes to show ya that your mind is your own monster / Reality is what you make it, if you take it away / You’re just a fish, like me, swimming in the powdered water…” 

From KRS-One’s philosophy to Eyedea’s various tracks, rap runs the spectrum of what content can and will be discussed. I think every rapper has pondered their existence or their reality in one form or another. Here, Eyedea compares human reality of living in “powdered water” to that of a fish swimming around in actual water. The differences you ask? Well, there’s not much because the rapper, who passed way too early like so many other greats, learns from the fish that “reality is what you make it.”

14. The Roots – The Hypnotic (1996)

“And slowly parted – reminiscin’ of when it started / It keep me feelin’ heavy hearted – a stolen moment periodic / Addicted to her presence like a narcotic / Though I wonder if she ever got it – the hypnotic / That faded like a dream sequence that persuaded / Beyond being infatuated – spiritually intoxicated / Comps are dated – I concentrated / On how to get in touch with her / Cause the fact of the matter remain that I miss the hypnotic…” 

I included this song for one because Questlove’s book inspired me to write this. I included it secondly because it was a toss up between this and Lost Boy’s Renee. Both are good songs in my opinion. As far as being a better song and better-told story with beats and lyrics that promote the idea that a story is being told, I’m going to go with the Hypnotic. Renee’s beat doesn’t match the sad story being told. Ultimately the payoff is weak as well. I don’t feel Freaky Tah brought the emotional touch Black Thought did with the Hypnotic, which basically tells a similar story.

Maybe I love the idea of Alana more than Renee or the fact that Black Thought tells this story of desperation so masterfully, I’m not sure. I know for sure though that Black Thought makes the most inconspicuous sexual reference of the millennium when he says Alana “lubricated his meridian points.” Damn Alana, why did you have to go?

15. Boogie Down Productions – Love’s Gonna Get’cha (Material Love) (1990)

I’m going to cheat here because KRS-One basically explains the entire song. While the following is not lyrics, it is the beginning of the story. Thanks Chris…

“Ya know that’s why man I be telling you all the time man, you know love, that word ‘love,’ is a very serious thing, and if you don’t watch out I tell ya, that (Love’s gonna get you) because a lot of people out here say “I love my car” or “I love my chain” or, or “I-I-I’m just in love with that girl over there” so, for all the people out there that fall in love with material items, we gonna bump the beat a little something like this…”

Don’t get it twisted here. KRS-One is not discussing the type of love like Black Thought had for Alana or Prince had for Apollonia or that Ralph Tresvant had for his candy girl or that ABC had for Iesha. He dissed material love. He’s warning about the dangers of love when it’s love for jewelry, sneakers, cars, and money. He stresses at the end you can like those things but not love them. Most of rap’s modern commercial culture is about these things and it has been for a long time. The discussion really could derail into rap’s influence on youth who can’t all have a “wicked jump shot” or rhyme like Pac so they resort to “slangin’ crack rock.” So some take the same route as the kid in this song. The pitfall of such behavior being exactly what KRS-One rapped about – you know, getting arrested, death, etc.

https://www.youtube.com/watch?v=5sQVSfM-AjA

16. Lupe Fiasco – He Say She Say (2006)

“She said to him / I want you to be a father / He’s your little boy and you don’t even bother / Like ‘brother’ without the R” 

“So he said to him / I want you to be a father / I’m your little boy and you don’t even bother / Like ‘brother’ without the R”

Lupe Fiasco goes all in on non-present Dad’s. He derides a father from the Mother’s perspective and then proceeds to mimic the mother’s derision from the son’s perspectives. The effect of which creates a situation where the first verse (the Mother’s) could be disregarded as another disappointed, frustrated mother playing the role of mother and father. However, when the son repeats his mother’s words, the words hit harder. The efect is that now the mother’s words are reinforced and much more difficult to reconcile. An example is when the mother tells the father that the son asks if his father is sick of them because he never picks the kid up. Then the son repeats this refrain but instead says his friends ask if the father is sick of the son because he never picks him up – notching up the stomach gut-punch effect of this similar question.

17. Kendrick Lamar – Keisha’s Song (2011)

“See a block away from Lueders park, I seen the El Camino parked / In her heart she hate it there, but in her mind she made it where / Nothing really matters, so she hit the back seat / Rosa Parks never a factor when she making ends meet…” 

Old men would say Kendrick Lamar has an old soul. He’s a throwback to the civil rights era, a prodigy of Public Enemy, a conductor on the underground railroad. His raps illustrate the struggle amidst struggle but seek to empower those within the struggle’s grasp. When he tells Keisha’s story, its hard not to feel her pain. She’s not ignorant of her situation, she feels and understands every bruise, every time she’s taken advantage of, and the pain of selling her body. Despite how intentional her actions are, Kendrick Lamar makes sure we understand Keisha is a victim.

18. Immortal Technique – Dance With The Devil (2001)

“He fiended for props like addicts with pipes and needles / So he felt he had to prove to everyone he was evil / A feeble-minded young man with infinite potential / The product of a ghetto-bred capitalistic mental”

I’ve listened to this song hundreds of times. Every time I find myself trying to figure out if this story is true like Immortal Technique wants us to believe. My god, if it is, well then I understand Technique a lot more. If not, then Tech is a masterful storyteller who, in this nine-minute gem, is able to make the listener feel like he or she is right in the streets with William and his boys witnessing a horrific act of violence by a son against his mother.

Also, I can’t discount how the Henry Mancini Love Story sample adds an ominous chill to this song. The mood of the lyrics is definitely matched up perfectly with the beat and that Phantom of the Opera like piano sample.

Honorable Mention: Common – Stolen Moments Part 1 – 3 (1997)

“There was a Hardy Boy mystery I was trying to solve / Can’t understand who the fuck was involved…” 

I threw this in here as an ode to one of my favorite albums of all time, Common’s One Day It Will All Make Sense. The story is kind of cheesy. And the cheese gets spread on, not for one but three different songs with different beats and guest artists Black Thought and Q-Tip. Each song tells a different part of the story. The second song is my personal favorite as far as the beat is concerned. I play it the most because the beat makes it work as a stand-alone song.

Common is a man cut from the same cloth as me in that the crime perpetrated is frustrating in various senses but the most frustrating thing Common states is that someone took his Donny Hathaway tape that he would’ve used to subside his frustration. I concur with Common, like Bob Marley said, “when the music hits you, you feel no pain.” Fucking punks – taking his Iverson’s AND his Donny Hathaway tape. The worst part is the culprit turns out to be his friend. And guess what??? He “pops the tape” in the deck as they are riding together.

[1] Even though I really meant the week of June 18th.

[2] One that Common quickly dispersed with The Bitch in Yoo. Though Cube’s style ultimately wins out because west coast gangsta rappers win the charts once Dr. Dre’s The Chronic comes out. By the way, Ice Cube was definitely wrong to feel dissed but I understand rap is an egotistical art medium. Any words about another man’s “game” are met with equal force and vitriol. So I understand why Cube was upset. If this beef had occurred in modern times where the effect of blogs and the internet would have amplified it by a million, then it might have made TMZ, the Huffington Post, and World Star front pages. You had a relatively new rapper with one previous respected, but not great selling album, going at an established star. This is like Canibus going after LL. The only bigger beef is obviously 2Pac-Biggie and Jay-Z-Nas. Again, I could write forever about this one.