Back when I was in high school, New York Magazine did an expose article on ‘prep school gangsters’. These were all kids who went to NYC private schools and I went to school with tons of them. From uptown to downtown, they were everywhere…
For the most part, they were bored rich kids who watched too much Yo! MTV Raps. During that time, I was deeply immersed in hip hop shit, I was obsessed. The whole “keeping it real” angle never really appealed to me so I stuck with just the music part. The prep school gangsters (who were rarely hard and usually retarded) were the kids who also liked rap. I’d be lying if I said it was much of a conversation piece but it was a commonality between us. As time went on, we all got older and people kinda scattered in their different directions. A thing I’ve noticed since maybe 1995 or so is that these prep school thugs love of “the game” was fleeting. After biggie died it seems they all just shrugged their shoulders and picked a new thing to be all about. Not to mention, it’s hard to be hard when you go to Vassar or U. Penn. In the last few years, these old people from the past have popped up here and there and it always bugs me out to see them. Mostly cause it’s amazing the directions these people have gone. Since I’m a fan of stereotypes, I figured it would be interesting to see all the reincarnations of the ‘post prep-school gangster’…at least the ones I’ve noticed:

1) The Wall Street Douche

When all is said and done, this was destiny for most of these kids. Sure, they rocked crazy polo sweaters and had 4 beepers, but when the chamber doors closed the gruff accent dropped and it was tea time with mommy and daddy (and possibly a butler). Their parents had this plan for them before “Rappers Delight” was ever recorded. No amount of fucking off in college or blunts smoked would ever change this path. Like Nas’ second album (that they probably kinda liked), It Was Written.

2) The Club Guy

Back in high school, there were club parties some of these dudes would throw. They were corny and full of the worst upper east side dick faces on the planet. They would play reggae, hip hop and shit like “come baby come” by k7. These dudes ruled that particular social scene with a smug grimace on their faces. But, as they got older, they didn’t leave the party. Their connections didn’t vanish so they went from high school club promoter to a regular club promoter. Not much of a change BUT you wouldn’t recognize them if you passed them on the street. Gone were the baggy jeans and baseball hat. They were replaced with some queer eye gear and hair gel. Very persian. The funniest thing about these guys is when I run into them, they still persist with the thuggy accent even though they look like Madonna back up dancers. I figure if you’re gonna let it go that hard, let it ALL go. Then again, these guys are all rich with super hot girlfriends so I can assume they could give a shit what I think.

3) The Fat Rap Guy

For some reason, they are always fat…and have goatees. These are the guys that stuck with the hip hop like their lives depended on it. Most of them were DJ’s and while I applaud their dedication, it is a blind dedication. They will swear up and down that KRS one is still amazing and how DJ Premier is incapable of making a half assed beat. They are purists to the point of delusion. They are also just setting themselves up for the ultimate life lesson when they realize (sometime down the line) that hip hop isn’t looking for the next 35 year old sensation…that shit will sting.

4) The Hipster

Not to be confused with club guys, these guys don’t go to Marquee and buy bottles. They’re more about the scene then the venue. From Girbaud to the tightest skinny jeans ever seen on a man, they’ve got the hair, the stubble and the tattoos. This one always bugs me out cause it’s doing a complete 180. Like if they could see what they were gonna become in high school, they’d kill themselves (or maybe just gay bash themselves).

Obviously, everyone is going to change a lot from high school into adulthood and beyond…but this shit is so telling of the reality that people never really change. In the mid 90′s hip hop was the hot shit. Now, it’s this hipster shit (is it rock? I think so but I can’t really tell…) These guys just went with what was there. There’s nothing wrong with getting sick of a music style or a scene, it happens. Shit, I make hip hop for a living and the last thing I wanna do now is listen to new rap. However, there’s a difference between expanding your horizons and abandoning something completely. It’s depressing to run into these types and when I tell them what I do, they look at me like; “You’re still into that shit? Don’t you read Vice Magazine?”

My issue with these types is that they reject any connection to that scene that occupied their lives for their most formidable years. It shows that, chances are, they were never really down with it
to begin with. It was a stepping stone to the next hip thing. In 5th grade, we would call someone like that a poser and I’m willing to bet, in 5th grade, most of these guys were frantically trying to figure out where to buy the new Garbage pail Kids so they could fit in. Fucking posers…