There are two different sides to RiFF RaFF aka. Jody Highroller.  On the one hand the former G’s to Gents contestant is that guy sporting MTV, BET and Bart Simpson tattoos, along with a jewelry selection that could make Ghostface shake his head in disbelief, whose look inspired James Franco’s character in the movie Spring Breakers and is part of a rap collective called Three Loco, along with comedians Andy Milonakis and Simon Rex.  On the flipside he’s well connected, able to count on producers Harry Fraud, Dame Grease and Diplo amongst his beat suppliers and having collaborated with respected rappers like Action Bronson, Meyhem Lauren, A$AP Rocky and Earl Sweatshirt.  Somewhere in his past there’s also an alleged affiliation with Swishahouse head honcho OG Ron C.

It’s tough to tell if he’s a new version of Ali G that the world hasn’t quite caught on to yet or if he really means it, maaan.

Either way, he does have an undeniable work ethic, having shot and released an insane amount of videos accompanying his prolific musical output.  Those videos are a big part of the hype RiFF RaFF has been able to generate.  They’re hilarious parodies (intentional or not) of southern rap subculture, memorable for their outlandishness and overall weirdness.

http://www.youtube.com/7ohbKidZLiA

The problem is that once you disconnect the music from the visuals, a lot of entertainment value is lost in the process.  That’s a feeling you can’t quite shake when listening to the Birth of an Icon mixtape, which serves as the perfect introduction to the Jody Highroller universe.  At the same time the music does hold up better than you’d expect considering RiFF RaFF works better as a comedic character than as a mere recording artist.  Dude isn’t a lyrical marvel by any stretch of the imagination but when paired with the right talent behind the boards the results are satisfying enough to warrant a listen away from your computer screen.  The beats and hooks are catchy, in that deliberately candy coated sunshine kind of way, and you can always count on Highroller for some ridiculous one-liners to be delivered in earnestness.  There are plenty of them throughout the 25 tracks that make up this tape.  Some prime examples include: “ice on my fingers/looks like I slapboxed a penguin” (Deion Sandals) or “Shook dice with Larry Bird down in Barcelona!” (Larry Bird).  The undeniable odd couple vibe transmitting from the collabo with Chief Keef might actually be sufficient motivation to check out this record.

http://youtube/nB9au3UBSqI

It’s tough to tell what the future will hold for RiFF RaFF, it could go both ways.  At his worst he’s a continuation of LMFAO’s brand of grating party-rap.  At his best he’s a guy with an ear for a cool beat that will get stuck in your head for days on end, never trying to overshadow his more skilled cohorts on a track.  The route taken will probably depend on whether or not he manages to keep working with respected producers and emcees who are grounded firmly in rap’s vibrant underground scene or if some major label decides to seriously cash in on his pop potential and pairs him with a supporting cast that completely disconnects him his hop-hop roots.  If that happens you’ll be glad to revisit his current output so you might as well enjoy it now.

What landed Jamal Barrow in jail could easily have been another ‘when keeping if real goes wrong’ sketch on the Chappelle’s Show. Everybody knows the backstory. No need to dwell on it too much: young kid gets thrust into the limelight and has to run with the ball after the untimely passing of the late great Christopher Wallace. He’s the biggest star on arguably the biggest hip-hop label at the time, Bad Boy Records, with the best in-house production team in the industry. How could this possibly go wrong? One nightclub shooting later, the next big thing ends up doing a ten year bid. Take that, take that.

It seemed that his legacy would be confined to two solid and highly underrated albums, his self-titled debut and ‘Godfather buried alive’. And his life could be summed up with a Bill Duke line from Menace II Society: “you know you done fucked up, right?”

Against all odds, all the drama ends up seeming as a mere prelude to Shyne’s actual recording career. After the jail time, converting to Judaism while incarcerated and getting deported to Belize upon release, Shyne aka Moses Levi releases the Gangland mixtape. Truth be told my expectations weren’t high for this one since he’d been deprived of The Hitmen’s production genius and at first glance didn’t sound like the nimble 21 year old rapper that exploded on the scene more than a decade ago. Gangland is a monster of a record through, to the point you actually feel like you’re doing it a disservice calling it a mere mixtape. Shyne comes across as the last real rapper alive of the course of the album’s 18 tracks and as a refreshing alternative to rap’s current batch of manufactured drug Kingpins, personified by the omnipresent Rick Ross.

Shyne’s fluidity on the mic has been replaced by a slower, hoarse flow and he’s trying to come to terms with the fact that he’s lost nearly ten years of his life. As such Gangland might not be a demonstration of skill, dude’s lost a step over the course of the last decade from a mere technical standpoint, but it does make for an utterly compelling record as a more contemplative Shyne emerged after all the trials and tribulations. At times he sounds bitter, other moments remorseful but always brutally honest. There’s no glorification of crime or his past actions. There are no excuses being made, shit happens. Gangland is a headphone masterpiece, one of those instances where a rapper’s words carry so much weight that they transcend nearly all of his limitations as an artist. Don’t get it twisted, Shyne is still a gifted rapper and gets to ride some gritty and bleak soundscapes as he takes you with him through his personal purgatory. There’s none of the gloss of his debut album and only a few nods to current trends, with some Lex Luger style drum programming and synths thrown in the mix. For the most part it’s that vintage boom-bap, Nuevo York aesthetic that’ll keep your head bopping throughout.

He’ll probably never be a household name again but if this tape is any indication he’s going to end up being one of rap’s brightest stars, on his own terms. The King of New York is back.

Recommended: You’re welcome, Meyer Lansky, King Judah, King David