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