The Chicago Years pt 1

Much to my chagrin, I got my start as a DJ over 20 years ago following up on an ad for a spotlight operator for a Rat Pack impersonation group, not the most glamours of jobs I know, but it was one of the best, if not the best I ever had. First day on the job I flat out lied to my new boss when the DJ didn’t show up, and told him I was a “Seasoned Vet” on the turntables at that point at the ripe age of 19. I was obviously ousted as a fraud right away but my new boss applauded my enthusiasm and kept me on board. What follows are some of the more colorful tales…….. that I can tell of course hahahaha.

First off and one of my favorite stories of all time is how I ended up with the name Diamond Entertainment in the first place. Its certainly not the most classy of names and quite frankly is reminiscent of a Strip Club which will make sense shortly. After A long night at work it was not uncommon for my boss to either leave me on the job so he could head out and party, or take me to the party and leave me in the car as he went and talked to some of his more…. Interesting friends lets say. Did it suck…. absolutely, some of the most boring nights ever( have to remember this was well before smart phones). My solution to this was to just go to sleep and an hr or so later, my boss would get back in the work truck and he would take me back downtown from the Chicago burbs. Well one night, I went to sleep around 2am and I wake up around 8am to my boss and his buddies laughing there ass off about how they just left me over night in the freezing Chicago winter out in a van. I was absolutely livid when the morning cold wore off, but these were not the type of people you talked back too… Capische? Well on the ride home while he was laughing his ass off again and he blurted out, “Jr(which is what they all called me since I was not Italian) you should name your business Diamond Entertainment….. cause if you fail as a DJ….. You could go right into Porn…. The day I moved from Chicago and headed back to the east coat I was gifted a jacked by my boss… It was embroidered with the Saying “Diamond Entertainment…. A Cut about the rest.”……. that jacket is my prize possession to this day and wear it every chance I get!!!

The Company I worked for in Chicago was absolutely top notch at the time but has a fairly built in audience and clients. One of those at the time was the Chicago Blackhawks. We got the help DJ and work on some of the charity and fundraiser type stuff for quite some time which was an absolute pleasure, super classy group of people for real!!! Among the many tales I could tell, my favorite of all being near the end of my time in Chicago. I had figured out to to at least pass as a good DJ and was on the main stage for the event b4 everyone moved to a different room to wrap up a silent auction. I obviously played the guests off as they went to another room but one of the people stayed behind. Just to set the stage , I am 20 feet elevated above the dance floor in a club type environment very much removed from the guests but I can certainly see them and they could certainly see me. The very nice lady who stayed behind had apparently taken a liking to me and did her best Elizabeth Hurley “Showgirls” impression for me. It was pretty surreal actually hahahah well at least till security did a once over of the room and very quietly dressed her and got her out of the room and I was in shock. Turns out she was dating and later married one of the Players on the team and in the wake of reality TV years later gained a little bit of fame. So I was not surprised when I read an article on TMZ about her cheating on her husband and them splitting… Can’t say I saw that one coming….. Awkward!!!!!!. True Story

I don’t wanna ruin all the fun on the first installment, but if you had not caught the drift on the kind of events I was working lemme leave ya with this. Along with the Weddings, my old boss would do Sinatra Impersonation work and was fantastic at it. Could really work a room, an unbelievable skill lost by most entertainers today. Seriously its a sight to see this guy in action…. Unreal. Anyway, He would often work do very small restaurants during the week which i never understood why. We were there for an hr or two tops and this guy would pay me my full DJ “freight” (Cost of Service) every time. We were at an absolutely stunning, very well know among the locals type restaurant during the Christmas season when during the middle of his show, while I was working the sound boards the Police surround the building with cruisers… with no lights on and casually send one Officer in. No one seems to be worried about this but me, I had a little bag of weed on me and thought my boss would kill me if he found out… HA!!!! little did I know. The cop casually strolls in… greeted at the door with a hug by what I believe to be the owners wife and was promptly escorted to the best table in the house to talk to a very serious man eating alone. After arriving at the table, the officer leaned over and whispered a few things to the man eating, he then smiled, put his officers cap back on and walked out of the building. To my amazement the show and dinner service had not skipped a beat and after finishing his dinner, talking to his friends and having about two bottles of wine the man, quietly left the building and got into the back of the cop car… Turns out this guy was a VERY serious person, and the cops let him finish his dinner before they arrested him…. I mean seriously…. still blows me away. That was the first time I saw what real power looked like…. and I will never forget it.

Health and Happiness!!! pt 2 coming soon!!!!