Stranger Than Fiction

As I mentioned in yesterday’s post, I’m a suburban kid. Well, “adult,” now, sadly. I grew up next-to-houses-that-all-look-the-same just as much as the next dude from a town, not a city. Living in the ‘burbs, I was too middle class to become a white collar criminal, too cut-and-dry to morph into a hardened hustler. The closest the teenage-me ever came to an illegal lifestyle was lifting packs of blank cassettes from a local electronic store; our very own Ocean’s 11-like operation, where my friend worked at the store and would take the bar-code off of the packaging and then toss the packs into an outside dumpster. There, myself or whichever other bootleg-crook would grab the pack from the trash, and go home with a fresh stock of future mixtapes.

Instead of causing mischief in those days, I was a Poindexter without the glasses. The town library was my favorite spot, and I’d breeze through a good three books a week. Primarily fiction of the horror/thriller/dark varieties. It’s a love of literature that still exists today—just last week I used my eyes to run through Richard Matheson’s What Dreams May Come, Chuck Palahniuk’s Diary and Dennis Lehane’s awesome Shutter Island (for the third time). All are highly recommended, by the way.

“So what’s all of this book-talk have to do with hip-hop?” You’re probably asking yourself that, and I can’t blame you. There’s a point to all of this, though. I’ve always had a special appreciation for storytelling songs, but I’ve noticed lately that I’ve gravitated more toward those that have plots beyond hustler tales. I respect records such as Jay-Z’s “Dead Presidents,” but prefer “Meet the Parents.” And all of the books that I’ve been reading lately have sent me into a bizarre-story-zone.

What I’ve realized in the process is that there’ve been several rap songs that fall into this realm. Weird first-person narratives, tragic concept stories. The tracks where an MC pushes his own creativity, not fearing any potential loss of connection with the listener. If written well, such conceptual storytelling will hit the bull’s-eye every time; if attempted by somebody in the Mims, page-turners on wax become paperweights.
Here’s a few of my personal favorite left-field storytelling rap songs. This isn’t definitive in any way, so I welcome you to offer your own faves. Just ask yourself before suggesting a song—“Would this make one fucked-up movie or not?”

Mr. Len ft. Jean Grae – “Taco Day”
Included on Mr. Len’s 2001 compilation Pity the Fool, “Taco Day” is the hands-down greatest kid-murders-up-his/her-students song of all time, if you ask me. Yes, Pearl Jam’s “Jeremy,” I’m looking at you. Len’s beat is a macabre beast in its own right, but this is Jean’s show. Grae, always a superior lyricist, blew me away with this 9-minute epic of a prom queen gone homicidal, slickly intercut with newsroom audio. Becky, the song’s main character, starts off as a popular girl harboring dominant insecurities and teetering sanity; by the song’s blood-soaked finale, she’s given family members and peers EZ-Pass access to the pearly gates. Devastating and sad. Makes me wish that Grae would give screenwriting a stab.

Lupe Fiasco – “The Cool”
I consider Lupe’s Food & Liquor to not only be the best rap album of 2006, but also a modern-day classic. A flawless LP. And the album cut that officially forever turned me into a Lupe apologist was this, a nightmarish Kanye West beat paired with a zombie tale that even George A. Romero (if you don’t know who Romero is, part of my horror-geek-heart will crumble) would have to applaud. Lupe continued The Cool’s story arch on his sophomore album, but nothing on Lupe Fiasco’s The Cool packs such a haunting punch as this record.

Louis Logic ft. Apathy and Celph Titled – “Best Friends”/”Revenge!!!”
Ten cool points instantly awarded if you also love Louis Logic’s 2003 sleeper Sin-a-Matic, a venerable one-stop-shop for fans of conceptual storytelling. The centerpiece is this two-parter, which starts off as Logic asks his friend Apathy to hang out with his girl while Logic hits the road. Unfortunately, Apathy lays the pipe, forcing Logic to recruit Celph Titled and enact life-ending revenge on Ap. The plan fumbles, though, and what we’re left with is a story of vengeance that’s as funny as it is vicious.

“Best Friends”


Cage – “The Subtle Art of the Break-Up Song”
Cage’s Hell’s Winter is another underappreciated gem, and this is the disc’s bleakest work of creative fiction. I was on the fence between citing “The Subtle Art of the Break-Up Song” or “Lord Have Mercy”—my favorite overall song on the album, but, honestly, I couldn’t even begin to explain what the fuck happens on “Lord Have Mercy.” It’s the rap equivalent of a David Lynch film—I love it even though I’m left utterly mystified. “Break-Up Song,” though, presents a clear-cut vision of domestic violence, only given Cage’s uniquely-disturbed sensibility.

BONUS: Souls of Mischief – “Anything Can Happen”
I’m cheating a bit with this one, being that its central plot is closer to straight criminology than these others. But it’s totally underrated, thus earning a slot here. The four Souls—Opio, Tajai, A-Plus, Phesto—spit a hook-free, continuous, multiple-POV yarn, where the accidental death of one’s mother is paid back in trigger-happy full. Their ’93 Til Infinity album is a classic in my world, and this is the track that I replay most of all. -Matt Barone

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  • Moving Sideways

    That is an incomplete list without mentioning Immortal Technique’s ‘Dance With the Devil’ or ‘You Never Know’.

  • General

    Royce da 5 9 – “Part of Me”

    Joe Budden – “In My Sleep”

  • DJ Postman

    Cosign on Lupe Fiasco. Both of his albums are instant classics.


    Most of Eminems catalog…”STAN” stands out, The Pharcydes”For better or worse”(fat lips verse), Gravediggaz”Diary of a madman” is a good listen…

  • Jerm

    I always enjoyed Outkast’s Art of Storytellin parts 1, 2, and 4. Andre is real nice with his storytellin, even when he kinda tells it in present tense, like “You Remix” with Lloyd and Nas, if that counts…

    Ludacris – “Runaway Love”

    DMX – “ATF”, “Heat”

    Chamillionaire – “Think Im Crazy”

    those are also nice

    • latino heat

      co-sign Jerm
      Think i’m Crazy was hot. people sleep on Chamillionaire. dude has crazy lyrics and wordplay and dosen’t even have to curse.

    • HNIC

      Has Outkast ever stated why they never made an Art of Storytelling Pt. 3? Or is it going to be a track on their next collaborative album that will be coming out in Neveruary 2030?



        • daz_oc

          I always took pt. 3 to be the remix which actually was not on an album, they just made a video for it with the puppets

  • Mas

    Aesop Rock- Fumes

  • http://XXL TheGodJustice

    Okay, I didn’t even start listening to the songs yet, and I cee JEAN GRAE’s fine ass!! OMG, that is one sexy chick. And to top it all off she’s a BEAST ON DA MIC!! Dat’s what makes her even sexier to me. Just my kind of girl 4 real.

  • BrooklynNY


    should have topped this list.

    • Pierzy


    • P. Harris

      CO SIGN!!!!!

      top of my list…

      • Lowedwn

        co-sgn that all day, that would definitely be one ill flick as would Biggie’s “Story to Tell”.

        Big L’s – “Casualties of a Dice Game” & “The Heist”

    • beaver

      didn’t think any1 would bring up
      “Undying Love”by NAs…dats a dope song..feels lik i got front row at a movie..
      great storytellin by NAs,,listen 2 it guys..

      • beaver

        oh yea..
        i just remembered..
        Eminems “Yellow Brick Road” off Encore..
        dats a dope song also..
        same shit 4 NAs Undying Love..
        Seems lik a movie 2 me..

  • latino heat

    A Story To Tell. Notorious B.I.G.

  • $ykotic/Don McCaine


    No Slick Rick?

  • abdulnasir

    co-sign on lupe’s “cool’ and chamillionaire’s “think i’m crazy”.

  • Super.Woman

    Joe Budden – “Secrets”

  • El Tico Loco

    $yk- I don’t think he was going for the obvious.

    But where’s Apathy’s “School” acting out characters was a dope ass concept.

    MC Lyte- Cappuchino

    • Lowedwn

      damn…gotta throw in Lyte’s “Georgie Porgie” too

  • zood

    Plenty by Slick Rick, one of my favourites being a Teenage Love.
    Lupe has plenty as well The instrumental and hip hop saved my life are a couple of my top rated.
    Brenda’s got a baby by Tupac.

  • P. Harris

    Q-tip’s verse on “Drink Away the Pain”

  • DJReMike

    lupe fiasco- and he gets the girl is another good one

  • Tony Grands

    Leftfield storytelling….

    Dr. Octagon’s “Halfsharkalligatorhalfman”

    I’ll throw in Geto Boy’s “Mind Playing Tricks On Me”. I think we hear the beat & systematically nod to the song, & granted, we know what the songs about, but the concept of the 3 stories was way ahead of it’s time.

    Also, see most of Brotha Lynch Hung’s catalog.

  • EmCDL

    Dang ain’t nobody mention the track “SpotRusherz” off OBFCL??? Thats one of my favorites right there, as well as most of Lupe’s stuff

  • capcobra

    the de la soul joint “millie pulled a gun on santa” plus “rewind” and “one love” from nas.


    jean crae is one of the best rapers i ever heard wish she had more material. that taco day was crazy as hell i like it

  • ?

    Stan- Eminem
    Duhhhh :]

  • thoreauly77

    * stands up and applauds this post *

    great drop! i teach english and i use immortal technique’s “dance with the devil” and aesop rock’s “no regrets” to teach plot diagram and theme. the kids love both because they are so fucked up and vivid.

    also, “one for the griot” by j-live; all of mr. lif’s album “i phantom”, and the streets’ album “a grand dont come for free”, both of which are continuous, linear story lines from beginning to end.

    hmm. good look on “taco day”.

    ghostface’s “masquerade” is also amazing. RA’s verse off of “uncommon valor” by jedi mind tricks….

    • Dub Sac

      It’s a little on the cheesey side, but “Tooken Back” off Pretty Toney has a nice narrative. I like that you get both voices, and the change of tone from Ghost between the 1st and 3rd verse.


    The Juggaknots- 1. Clear blue skies 2. I’m a kill you 3.Loosifa

  • Dub Sac

    Ghostface has stories for days – “Malcom,” “Alex (Stolen Script)” & “Scary Hours” are some of my favorites.

    “Talking In My Sleep” by Elzhi is one of my more recent favorites. Qualifies for heavy rewinds.

  • Federal Ranga

    EmCDL, Grand$, $yk, P, Tico, Paris what up, niggaz?! We in the house…. anyways

    Are you niggaz serious? I like all the aforementioned tracks, but come on… Em got that bugged out story shit on lock. about half of the Slim Shady LP was a bunch of crazy ass mufuckin stories…

    Bonnie & Clyde 97?
    Brain Damage?
    As The World Turns? Shit, I could go on!!!

    Who could forget Murder She Wrote. Slim tells some pretty weird ass tales, yo.

    E6 up ya’ll… E7 preppin!


    • Tony Grands


      What’s good, Fed!?

      Co-sign SSLP. One of the best hip hop albums ever, story-wise AND lyrically.

      *sidenote: Any of y’all cats catch that CNN video of Michael Jackson’s ghost walking across the hallway in his bedroom @ Neverland Ranch?

    • Federal Ranga

      Thats right E7 commin soon. This next vlog is gonna be another classic. For anyone that has yet to watch my vlog series, please check it out, because I promise that you will not be disappointed. These vlogs are comedy at its finest.

      Classic hood shit

  • Victor

    Good work Matt, your turning out to be an astute writer with a good knowledge of hip hop. 93 Till Infinity is a near flawless LP

    I’ve never given cage much time and the track didnt really change my mind.

    I heard the first part of that louis logic track on an Apathy mixtape but hadnt heard the 2nd part which is equally illy.

    Jean Grae is ridiculous on the mic, she stands tall wiv lauryn hill and mc lyte as the premier female lyricist. I had no clue she was smoking hot either, a testament to her ability that she shunned the use of her looks!

  • eesco

    I’m diggin th list but he said about lupe that on hid second cd he didnthave anything as haunting as the the cool on his first lp yo u gotta check the coolest on the second lp. the beat alone is haunting and the story is bananas. ( to a crying dihonered baby mama whos the mama to a daughter that I had fathered from afar, my new lady gave me a mercedes and a necklace with a solid gold key like th starter of a car the opener of a door or two pounds of raw, you gave me a baby but what about lately, then ha ha ha’d right up in her face G there more fish in the sea, I’m on my mission to be the coolest nigga) that shit is cold

  • lefthand slim

    can’t believe that no one thought to mention murs….if you have never heard 1st love or trevor an them go find them ASAP

  • beaver

    Mr. Len ft. Jean Grae – “Taco Day” is so fuckin dope..
    this my 1st time listenin..dope track..gotta download quick..ha

  • Jamal7Mile

    I had no idea Mr. Len put in that much work with other artists like Jean Grae! I became a diehard Len fan on this very site when he used to post audio sets almost everyday. He never screamed over the tracks and still knew how to tell a story with track selections alone. Be sure to check out the Lunchtime w/Mr. Len posts on this site.

    Great drop, Matt! Check out this British author named Brian Lumley who wrote the “Necroscope” series since you like monsters and otherworldly type fiction. A guaranteed page-turner! You won’t believe it!!

    A few other stories not mentioned:

    Murder Was The Case
    Just Lyke Compton – Quik
    Hypnotic – The Roots
    Once Upon A Time In The Projects – Ice Cube
    Gangsta’s Fairytale – Cube
    Streiht Up Menace – MC Eiht

  • Curtis75Black

    I have to remember this is a mainstream Hip hop site. I always find it funny when threads/blogs like this in particular come up, the same songs are always mentioned, not saying they don’t deserve it but Damn !! I was just wondering why no one ever mentioned
    Common’s – Stolen Moments ?

  • chillin mayne

    whoaaaaaaaaaaa, yall missin a couple hot ones

    I’ve Committed Murder – macy gray, mos def

    Children’s Story – Slick Rick

    and little weapon by Lupe fiasco is xtra hot son

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