06/24/2014 11:55 am ET Updated Aug 23, 2014

Trapped in the Booth: Part 2

Disclaimer: This is a semi-fictionalized version of my all-too-real experiences working as a DJ in New York City. Most of the names of venues, organizations or people mentioned herein have been changed or, in some instances, totally pulled out of my ass so stop even trying to guess, cool? Cool.

I have an especially bone-chilling list on Twitter that I drunkenly dubbed "Nightlife Hellhole." Usually I avoid it at all costs, for "Nightlife Hellhole" is just what it sounds like - a dingy inferno of delusion, dashed dreams, desperation and despair. But late one night last week after a particularly exhausting gig I took a dangerous trip down the rabbit ho- pardon me, down the Hellhole. And it was just as barren as I remembered.

As I clicked through profiles of various dim-eyed promoters, club-owners with too-smart haircuts, and former bottle service waitresses I used to dance to Aaliyah with at the end of my sets, I came across a profile that made me pause and shed a patented 4AM tear.

The handle belonged to a female DJ I knew only vaguely, mostly through social media. Her bio read: "Blogger, Sound Designer, Branding Expert. Celebrity DJ. "

Blogger. Sound Designer. Branding Expert. Celebrity DJ.

Now personally I've always been confused by the term "Celebrity DJ." Is the Celebrity DJ a DJ who is himself a celebrity? Or, more pitifully, is a Celebrity DJ a DJ who often plays in the presence of celebrities, kinda like Heidi Fleiss is a "Celebrity Pimp"? Can a Celebrity DJ, one who is himself a celebrity, be a Celebrity DJ without playing for many other celebrities as well? Conversely, can a Celebrity DJ, the kind who is not famous of his own accord and yet plays other people's songs in front of celebrities, become a Celebrity DJ, one who is famous by his own achievement? Most importantly, who makes these decisions?! WHO IS THE ARBITER OF CELEBRITY DJ-DOM?!

Regardless of definition, contemporary nightlife is laden with Celebrity DJs, at least to the extent that we can trust a Twitter bio (and I trust them all implicitly).

As I've mentioned before, I don't think I'd call myself a Celebrity DJ, although DJing has certainly brought me into contact with various celebrities. Ke$ha once exited a party I was spinning because I played a Ke$ha song. Malin Ackerman slipped me a 20 to play a mysterious lullaby she referred to as "Yellow Diamonds" by Rihanna at a Cosmo party. And yes, Hills luminary Lo Bosworth has labelled me a "pretty good DJ." To my face.

For some special DJs the relationship between nightlife and celebrity, faux or otherwise, seems easy and maybe even mutually beneficial. If you look at Instagram or a gossip blog, it appears like these chosen DJs head out into the night to spin their celebrity-hosted event and exit the venue casually laughing their drunken heads off with Katy Perry while the paparazzi snap away.

Me? I somehow always manage, even with the best intentions, to horrify even the lowliest of reality star with either my coarse attempts at a "joke" or my "play it cool, DJ" shtick, the biggest acting fail since Beyonce took to the screen.

As I continued my trip through Nightlife Hellhole and combed the depths of my mind about just what a Celebrity DJ is, my thoughts wandered to the many legendary tales of me unitentionally frightening famous people at work.

My favorite example happened whilst DJing an end-of-summer pool party for a large vodka company that shall remain nameless. (It's heavily endorsed by a perennially name-shifting hip-hop mogul who rose to fame in the mid '90s and also gave Aubrey O'Day her 15 minutes. But I'm not naming names, guys.)

The main draw of the event, aside from the obvious enticement of a pool in Brooklyn and of course, my beautiful face, was that it was to be hosted by Gossip Girl ingenue Penn Badgley.

I arrived on that Saturday afternoon around 12PM to set up, still fully aboard the hangover express from the night before. It was a blistering hot August day out on the pool deck, maybe 95 degrees, and, being Jewish, I began sweating immediately upon arrival. A PR intern, shuffling around in her Herve Leger bandage dress and pre-party flip-flops, gave me the lay of the land. "Over there is the bar, there is the photo booth, here is where Penn will be sitting," she explained. Then, she turned and pointed her finger towards the heavens, "and here is your booth!"

I spun around and gazed in horror. There it was, a DJ booth made of nightmares, dubiously situated atop a rickety old lifeguard tower. "Great!" I squeaked out only semi-believably, dabbing my brow.

I climbed the ladder to the booth (this sentence never precedes good things), situated my records, needles and computer, and proceeded to peer over the edge of the tower I was sure would play host to my demise. I could feel my bottom clench, quickly remembering my life-long suffocating fear of heights. However, I had just recently seen a commercial for the US Army that touted the tagline "Army Strong," a call to stare adversity right in the face and punch it the fuck out. "DJ Strong," I thought to myself as I swallowed hard, placed the needle of the record and started to play tunes.

Somewhere between the first and second hour of the party, between alternating bouts of vertigo and sunstroke, I discovered that a bottle of sponsored liquor had been conveniently stashed for me underneath the the booth. "YASSSS Biiitttcchhh" I thought as a I twisted off the top, "Daddy needs his medicine!" (The sun had clearly impaired by logic). I turned out to be my complete and utter downfall.

It was around the 5th or 6th swig, just when things were starting to look rather rosy, when my aquatic-rescue fort / DJ citadel began to rattle. I noticed the same PR intern from earlier, now resplendent in black patent-leather Louboutins, shimmying her way up the ladder. She heaved herself onto the platform and and panted, "Hey Louie! The photographers want to take some pictures of you and Penn. Can Penn come up here?"

"Surely!" I slurred (surely?), now dripping with vodka shvitz but caring about it way less than I had earlier.

My fortress was then once again scaled, this time by a slender, moppy haired brunette and before I knew it, there I was standing mere inches from the 3rd most important star of Gossip Girl himself.

"Hi, I'm Penn," said Penn Badgley.

"And I'm Louie," said myself softly, futilely attempting to mask my vodka breath.

We shook hands and turned to face the swarm* (*3) photographers stationed at the bottom of the ladder of my musical minarette. Now, posed pictures at events are always awkward. Someone should really teach a class on what exactly a person should do in these scenarios. I usually go with the "I'm miserable-but-chic" facial expression I learned from Kate Moss as a teenager and call it a day. Any attempt at smiling and I end up looking like a 12 year old who just smoked crack for the first time, only less cute.

Compounding the normal challenges of event photos, I slowly became aware of the fairly ample moisture dripping down my neck, slowly sliding toward my upper back and splashing onto Penn's perfectly manicured hand, which was, at present, resting on my shoulder.

Penn, of course, looked fresh as a daisy, as if heat was an absolute non-factor in his life (the sun and its awesome powers apparently have no negative effect on the famous). I, on the other hand, could now add "massive anxiety because I'm sweating all over a complete stranger" to the multitude of reasons why I was currently perspiring all over Dan Humphrey.

Halfway through the shoot, it hit Penn that his fingers were soaked. He pulled his hand off my shoulder, hollered "hold on!" to the photogs, and wiped his drenched paw on a promotional towel that was hanging over the side of the lifeguard tower. It was also right about this time that my buzz turned on me and I basically wanted to dive head-first off the tower into the pool in humiliation, and spend the rest of the party hanging out under water.

In retrospect, this would have been significantly better than what I actually did next.

"I'm sorry, it's so fucking hot," I said. "No problem at all!," Penn replied. "It's excruciating up here." (Penn was actually a very nice young man.)

"You know," and here is why I should never be allowed to drink in public, "I could cool you down with a nice, refreshing vodka shower!" I thought I joked, pointing to the half-empty comped bottle on the floor. "It'll make for a pretty funny picture. It'll be just like Nelly's "Tipdrill" video!"

Dated Nelly references and all, Penn turned and looked at me a little cross-eyed. "Ha, no thanks," he said with utter reticence and turned back to face the shutterbugs.

"Leave it there, buddy" is probably what a rational person would have thought next. I, however, thought, "HMM, Maybe he didn't get the joke the first time? How can I help him? How can I aid Penn Badgely, 8-time Teen Choice Award nominee, in seeing what an utterly hilarious joke I just made?"

It was here, in my drunken, fried lunacy, that I then proceeded to lean down, pick up the half-full comped vodka bottle and hold it over the former Mr. Blake Lively's gorgeous head with a dopey smile plastered on my face. "See! It'll be hilarious!"

Disclaimer: I want to be clear that I never had any intention of actually dousing Mr. Badgley in fine vodka. The bottle was capped and it would have been merely a mime, of course. But like any sane person would, PB looked back in me in abject horror, something like Marion Crane when a knife-brandishing Norman Bates pulls back the shower curtain in his dead mom's dress.

"Woah! Nah, seriously that's okay. Can you put that down?" he said holding his hands over his face to shield himself. Uh oh. "Oh no, I was just kidding!" I said, attempting to salvage any last shreds of my dignity. "I would never actually pour vodka all over you, Penn! It was just a joke because, ya know, rappers in videos pour [insert unnamable brand of vodka here] on girls? Haha, get it?" But there was no watering hole in this desert. "Let's just finish these pictures," said Penn, wholly unamused.

My Lonely Boy rendezvous continued for another excruciating 30 seconds of awkward posing and fake smiles before Penn jumped on the ladder out of my sun fortress. "Thanks, I'm so sorry again" I blurted out as he descended. He gave me a half-hearted smile back, then turned and ran full tilt across the pool deck toward the exit, leaving me to my solitude, high atop my Obelisk of Shame.

Years of reflection and I'm now pretty clear that this behavior alone has probably forever excluded me from the Celebrity DJ club. I cannot be trusted around celebrities. If I had ever considered adding that title to my Twitter bio, that August afternoon by the pool with Penn had certainly hammered the final nail into that coffin. Which is cool, I guess.

Although I will tell you that the next day a prominent nightlife website covering the event posted pictures from the party complete with a series of Penn and I in stationed in DJ Rapunzel's castle. The main photo they featured was taken while we were shaking hands and life was good, moments before I straight-up napalmed any possible future as Mrs. Badgley. We were smiling and looking pretty damn chummy, if I do say so myself. So if the Celebrity DJ thing is just an illusion anyway, maybe I did pull it off there for that first 30 seconds, just enough to get over, get the photo and look like a cool guy. Right before I playfully offered to bathe a CW star in liquor.