Somewhere, deep within my father’s mid-Missouri basement, are at least a couple of large boxes filled with an assortment of Betamax and VHS tapes filled with episodes of ‘Late Night with David Letterman.’

I wish someone would comb through all 1,819 episodes of Letterman’s ‘Late Night’ and put them on the Internet in easily digestible video clips like we see every morning from Fallon, Meyers, Kimmel, Stewart, Colbert and even Letterman’s own current ‘The Late Show.’ Yes, some of this stuff is on YouTube, but you kind of have to know what you’re looking for to be able to find it. It’s difficult to come across the hidden gem.

I think there’s a misconception that people under a certain age today don’t quite realize what a genius David Letterman was when he hosted ‘Late Night.’ The truth is, even back in the 1980s, people who didn’t stay up to watch Letterman every night didn’t know Letterman was a genius. There were no morning Internet clips to get yourself caught up. It was either “watch the show” or just not know what happened.

When ‘Late Night with David Letterman’ first premiered, my parents banned me from watching the show because they assumed for some reason that Letterman was “dirty.” Which, of course, made me want to watch Letterman even more.

(As a side note: it should probably go without saying that today my mother loves David Letterman and that fact makes me a little sad.)

I’d try to sneak in a show every now and then (with the volume turned way down so my parents would not hear Dave being “dirty”), usually during the summer when my parents had gone to bed and I didn’t have to get up for school. Plus, living in the Midwest at the time, Letterman started at 11:30 p.m., which still to this day seems like a reasonable time for a late night show to start. (The thing I miss the most about living in the Midwest is the Central Time Zone start times.)

Letterman made me feel like someone else out there understood that this was all bullshit.

It wasn’t until junior high school that I really started to appreciate what I was staying up so late to watch.

1986 was a weird year for me. We had moved from a relatively small Missouri town to a much larger city (at least comparatively) and, as an only child starting in a new school system, it wasn’t easy for me to adapt and I didn’t make many friends right away. I was really miserable. This is the time period that I really got into Letterman and, while watching, it was really the only time I was happy.

To watch during the school year, I would record Letterman on our old Betamax VCR, then, later (after my parents finally accepted they were on the losing side of the VCR format wars), on our brand spanking new VHS machine. I’d wake up every morning at 5:45 a.m. so I could watch Letterman before school. Because, again, if you missed one of Letterman’s classic bits, that was that – you missed it.

While the kids at school were telling crass actual dirty jokes, Letterman’s humor was perverse. While he was skewing the concept of television, what he was really doing was poking holes in the concept of societal norms -- norms that at the time were making me unhappy in my new surroundings. Letterman made me feel like someone else out there understood that this was all bullshit. Knowing it was bullshit made me happy. Letterman wasn’t “cool” (even though he was, but not in the sense that someone like Fallon or even Carson are/was cool), but his irreverence spoke to a hopelessly uncool kid like myself.

I couldn’t figure out at first why I was so sad on Thursday after learning about Letterman’s decision to retire. I do still watch the show from time to time, and I still think Letterman is the best interviewer working today, when he wants to be. But, I wasn’t a devoted watcher like I once was – and I knew this day would be coming sooner rather than later. But, yet, there it was: An immense feeling of sadness.

One afternoon, in the school cafeteria -- sitting near some other kids so it appeared like I wasn’t sitting alone, but far enough away that these particular kids wouldn’t think I was trying to sit near them -- I quoted Letterman’s show from the night before. It got a laugh. Now, I didn’t become friends with those particular kids, but I started quoting Letterman more and more often. I soon found other kids who also loved Letterman -- which was startling for two reasons: a) I was actually making friends, and b) I had no idea that other people watched Letterman.

The format of ‘Late Night with David Letterman’ had a way of making me feel like I was the only one watching – which is in stark contrast to a show like Fallon, which has a way of making it feel like everyone is watching. (And, according to the ratings, that might actually be true.) Letterman rejoiced when something went wrong with a bit; Fallon rejoices when everything goes right. Circa 1987 David Letterman and circa 2014 Jimmy Fallon -- both now experts at what they are trying to accomplish -- could not be more different. And that’s okay! But, I do wonder if there’s a junior high kid out there right now who feels that connection toward Fallon as I did – and many others did – toward Letterman.

I wonder if someday, as that current junior high kid inches closer and closer to 40, if he or she will feel this same amount of sadness the day that Fallon retires. I hope so.

Mike Ryan is the senior editor of ScreenCrush. You can contact him directly on Twitter.