With the recent passing of Jerry Heller (aka ‘the Jew who broke up my crew’ according to one Mr. O’Shea Jackson), it seems like the appropriate juncture to reflect on the long, storied tradition of allegedly shiesty music managers, which have become as a much a cliché as fat gold chains were to the ’80s and wearing designer kilts on stage are to the 2K10s.

Record labels are notorious for being ‘paper gangsters’ who get young, naive artists to sign recording contracts dooming them to years of debt and a tiny fraction of the profits from whatever music they eventually sell, and managers have tended to prey upon these same opportunities. Shit, if I’d been offered a Jeep Cherokee, five pairs of Nike Air Force Ones, and two Le Coq Sportif tracksuits when I was 17 I would have signed my life away too!

Despite the picture painted in the N.W.A biopic/Beats By Dre infomercial Straight Outta Compton, it’s clear that Eazy-E and Mr. Heller knew exactly what they were doing when they drew up the contracts for the rest of the Ruthless Records roster, safe in the knowledge that they were merely continuing the long-standing tradition of milking their artists for every drop of blood, sweat and tears legally owed to them by virtue of a recording contract and the fact that they could afford a half-decent lawyer.

One aspect of the film that did ring true is the scenario where one member of the crew realises that he’s being royally effed in the proverbial ‘A’, jumps ship and is then labeled as a traitor by the remaining members, who later figure out that he was right all along and follow suit. An almost identical situation occurred over in Philadelphia, where local heroes the Hilltop Hustlers (consisting of Steady B, Cool C, DJ Tat Money and Three Times Dope) fell out once EST, Chuck Nice and DJ Woody Wood realised that the crew’s manager, one Lawrence Goodman, was keeping a rather large piece of the pie for himself while they were paid in “Newports and Puma sweats”, as 3rd Bass once put it.

The resulting fall-out saw Steady B and Cool C staying loyal to L.G. and dissing 3xD lookalikes in their videos, a situation that allegedly escalated when the now rival crews ran into each other at a local basketball court and “somebody threw a quarter at EST”, sparking off a fist fight. As with N.W.A., Steady and C eventually came to their senses a few years later when they discovered that yes, they had in fact been getting shafted by their manager and all was forgiven with the acknickulous trio. Sadly, their resulting money problems spiralled into a series of bank robberies which resulted in life sentences and a trip to death row.

Over in New York, Marley Marl was experiencing similar headaches with the Cold Chillin’ Records after having previously released records by founding Juice Crew members on the aforementioned Lawrence Goodman’s Pop Art label (a decision which prompted Mr. Goodman to record Cool C’s record ‘Juice Crew Dis’ in retaliation). Co-owned by the Juice Crew’s manager Tyrone ‘Fly Ty’ Williams and with a lucrative distribution deal via Warner Bros. under their belt, Cold Chillin’ proved to be another classic example of why letting your manager write your record contract is rarely a wise move. After several years of producing hit records for the label and receiving little more than upfront cash, Marley jumped ship with two of his youngest artists (Craig G and Intelligent Hoodlum aka Tragedy) and sued for his publishing, eventually winning the case in what proved to be a particularly fortuitous move given the subsequent popularity of sampling Biz Markie, Kool G Rap, and Big Daddy Kane records in the years to come.

Likewise, Dr. Dre jumped out of the frying pan and into the fire when he ditched Eazy and Heller to partner up with Suge Knight over at Death Row Records before that situation turned sour and he started the still-lucrative Aftermath Entertainment (which produced the golden geese known as 50 Cent and Eminem), while Ice Cube apparently took notes from his time at Ruthless if the history of his Street Knowledge Records is anything to go by—almost everyone ever signed to the label would later make a diss track against Cube or ended up in jail.

Many of these unfortunate situations could have been prevented if the artists involved had followed three simple rules:

1. Don’t sign to a label owned by your manager.
2. Never trust a lawyer provided by your record label.
3. Never do business with your cousin.

There’s also the whole issue of two generations of rappers who signed away their publishing and never received a cent in royalties despite selling a boatload of records, but that’s a tale for another day…