Recollections around working the overnight shift and some of the characters I’d encounter…

Have you ever found yourself out and about really late at night? I mean reeeeally late, say 3:00 or 4:00 am? There’s a certain atmosphere to the outside world when you’re navigating it during those overnight hours – the streets are empty, stores are mostly closed, everything is dark and everyone is sleeping. It looks different, it feels different. Heading into a 24-hour establishment is a little odd too. What are any of us doing here at this hour? By all rights we shouldn’t even be here.

Twice in my life I found myself working the graveyard shift at Walgreens, the retail drugstore chain, and with plenty of hindsight (this was 20 years ago!) I can safely say it was an interesting experience. Working overnights is definitely not for everyone, but if you have a natural tendency to stay up at all hours of the night and can deal with the fact that your working “day” will be both mind-numbingly boring and also super freaking weird then maybe it’s for you.

There are, of course, pros and cons to working 3rd shift, especially when it comes to your level of social interaction with the world. If you’re an introvert like me, then you’ll likely enjoy being able to put in your 8 hours without having to interact with the normal amount of people you would average during the daytime. Sweet!

However, not only will socializing at a reasonable hour with your friends and family become increasingly difficult, but you may also tend to fill that void with your coworkers and the types of customers that you’ll encounter. I have to say that the most interesting and oddball customers I ever dealt with in that near-decade of working retail came through when the rest of the world was fast asleep. Drunks, weirdos, those who are lost and wandering, people who you can tell take no joy in being awake at that time and those who are completely accustomed to it. Most of the time, there’s a reason they’re up and shopping at that hour and it’s not because they’re super well-adjusted by societal standards…

Two such patrons stand out in my mind and if you’re up for it I’ll tell a few little anecdotes about them.

 

The First Part

The first time I worked overnight was when I moved from my hometown of Orlando up to Tallahassee for a spell. Having depleted the meager savings in my checking account that I was living off of, I found myself in dire need of employment and foolishly I thought I could waltz into the local Walgreens and get a job working in the photo lab (since that’s what I was doing in Orlando before packing everything up for Tallahassee). Turns out the real world doesn’t work that way and my plans were foiled, but the store manager was kind enough to offer me a position for the 3rd shift in their 24-hour store. This was new for me – my previous store was only open until midnight.

But hey — since I needed that paycheck, I agreed. Shortly afterwards I was paired up with a manager who showed me the ropes. His name was Mr. Anderson, and quite unlike Keanu’s character in The Matrix, he was a Southern man whose family would take him on weekly “hunts” to find roadkill to cook up and eat for supper. He was nice enough but since I’d already worked at Walgreens before there wasn’t much training needed and he kinda left me to my own devices. From the hours of 11:30pm to 7:00am it was just the two of us working in the store, and he liked to keep to himself.

Work was alright but life in general got strange. When you’re in your early twenties and living in a college town but wake up around 8pm ahead of your 11pm shift, well, you’d be hard-pressed to find anyone that wants to hang out at that time of night. Likewise, getting off work at 7:30am means nobody wants to see you in the morning either. Have you ever been excited to hang out with your weirdo friend at 8:00am on a weekday?? The timing is just really inconvenient for everyone.

Before long I was beginning to feel isolated not only from my friends in town, but also from the general public. It was super easy to fall into a Me vs “Normal People” mentality as I lost sense of what it was like to be on a typical sleep schedule. Another thing I hadn’t anticipated was the clear separation felt between the daytime and evening employees vs the overnighters. You see both crews at the beginning and end of your shift, but there’s such a short period of overlap that you never really gel – or at least I didn’t. Hence, I was on my own.

Enter “Number One”: the first customer I’m going to tell you about. From the outset, I was instructed to call him Number One because, according to him, he was voted the “Number 1 Firefighter in America”. Who ran this poll and bestowed upon him this incredible accolade? Probably someone that existed solely in his own mind. But that’s beside the point.

Number One was an older gentleman who had nothing better to do at 3:00am than to take a walk down to his local Walgreens and follow me around while I tried to get some work done. He would regale me for hours with stories about his time as a firefighter, the repair work being done on his Chevy Cavalier, his time as a firefighter, meeting the NYC firefighters who were first responders during 9/11, his time as a firefighter, how much the FDNY loved him, his time as a firefighter and when he was voted the Number One Firefighter in America. He may have also mentioned he was a firefighter before retirement.

Number One was pretty harmless and because of this I got to a point where I’d stopped attempting to engage him and would just let him talk while I concentrated on my job duties. He was an older guy, probably in his late 70’s / early 80’s, and never spoke of any family or friends (besides the FDNY Fire Chief being his BFF and all). Because of this I surmised that he was just a lonely guy; being able to come into Walgreens overnight helped him get that socialization that he needed and likely wouldn’t have been able to find during “normal” business hours.

Despite never buying anything and being incredibly eccentric he was always nice to me and even named me “Harry” because he thought I looked like Harry Potter (a character he only knew because one of the films had just come out and Daniel Radcliffe was on the cover of a magazine [to clarify – I didn’t look like Harry Potter!]). I strongly suspect he had an issue with remembering names anyway – heck, I can’t recall him ever telling me his real name.

To this day whenever I see anything about New York City firefighters I think of Number One with his Members Only jacket and collection of Fire Dept ballcaps he’d rotate through every night – sometimes NYC, sometimes San Francisco, Honolulu, Kansas City, etc. He bragged that they were gifted to him by those fire departments themselves, but I knew better.

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After a while things in my personal life came to a head and I decided to move back down to Orlando – my time in Tallahassee wasn’t a total failure but it didn’t exactly feel like a success either. A lot of that definitely has to do with working the overnight shift and the aforementioned social isolation that can occur, but to be honest, things weren’t going to work out for me there regardless.

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Second Time Around

The next time I worked overnight was, interestingly enough, after another failed move. Similar story – my personal life was not going great and I thought a change of scenery would be nice! Off to California I went, but things didn’t quite go as I’d hoped and before long I was back in Orlando in need of a job.

Check me out, strolling into Walgreens yet again with the bright idea that I could just get my old job back with no issues! Predictably, things didn’t work out that way but I gladly accepted the overnight position on offer since I’d done it before and nobody else wanted to (also, yeah, I really really really needed a job). Deja freaking vu.

At this point in my life I had no “IRL” social life to speak of, however I rather luckily had a great bunch of friends from an online message board who lived all around the world. This was handy because my free time matched up with their free time. With social isolation not being a concern this time around, I found myself much happier with the graveyard shift. Not to mention there were 3 of us per shift and my manager was cool.

The store I worked at was near Walt Disney World and we’d get these little waves of customers that worked late at the theme parks and would head in on their way home. This helped with the monotony of an empty store because Disney cast members can be a rowdy yet fun bunch, but we certainly had long periods with no customers at all.

Much like Number One in Tallahassee (but thankfully far less frequently), we had a regular visitor who’d walk over to the store during those dead hours. To us employees his name was “Tropicana Hat” but I never called him that to his face. No idea about his real name, just that he always wore a bucket hat with the Tropicana orange juice logo on it – old, dirty and tattered.

Tropicana Hat Guy was not harmless like Number One. They were both elderly white men with health issues but that is where the comparisons end. Frankly, he was a mean old guy. Not in the lovable “Grumpy Old Men” way, more like the abusive grandfather with whom your family has cut off contact. This is a man who came into the store looking for something or someone to complain about, always itching for an argument no matter how trivial. In hindsight I get that he might’ve been doing this for the same reasons as Number One – namely, a lack of family and friends in his life – but it didn’t make him any easier to deal with.

Well, I say nobody in his life, but he did have a caretaker who would come to his apartment to help him out. Naturally, I only know this because he would make unprompted racist comments about her, usually while comparing her ethnicity to a coworker of mine.

One thing I can say is that his nastiness could be so over the top that it became funny to us – “oh shit, here comes Tropicana Hat, get ready”. What’s wrong tonight? “Your drinks are too cold!“. Hmm, yesterday he yelled about the drinks being too warm. Oh look, he’s having a tantrum and banging his fist on the counter because he beat one of us to the register… “Can’t get any goddamn service around here!”

My favorite moment of his was when Walgreens started automatically printing coupons with the receipts and after I’d handed him one, he asked what it was for? I replied back that it’s a coupon for your next visit. “Well I’ll use it now then”, he grumbled back. “Actually, it won’t be valid until tomorrow”, I explained. He examined it for a few beats and then in his most miserable cadence said, “What’s the point? I’ll be dead by then anyway”.

Tropicana Hat didn’t die the next day, nor the following, or even the remainder of my time working overnights. Soon enough I went back to a “normal” shift and began running the photo lab again. Left retail a while later to begin working in IT and never thought about him until recently. I suppose he probably is dead by now, as this story was just over 20 years ago. But then again you never know, sometimes the mean ones outlive us all…

Like I said, working overnights isn’t for everyone but I’m glad that I was able to do it both times. Who knows, maybe one day I’ll have a job that lets me work those hours again… hopefully with fewer oddball interactions though.