I recently started re-reading the 1st edition AD&D Players Handbook (mainly as a PDF on my iPad mini whilst on the bus, so I haven’t gotten very far yet). Like everything else written by Gary Gygax during his time at TSR, I find the text quite enjoyable, and am discovering minor things that I never noticed before (or perhaps have long forgotten). More generally, I now appreciate that Gygax’s idiosyncratic writing style actually was part of AD&D’s appeal 30+ years ago, not a barrier to it.
By chance, I stumbled upon this post by Trent Foster from 2009 that makes essentially this point (though far better than I could):
The secret of AD&D's marketing success in its peak years (early 80s) was based on a sort of paradox, or even a lie -- the game was aimed at, and written for, adults, even though the core audience was actually kids aged about 10-14. These kids were the ones buying the books and playing the game (and even submitting stuff to Dragon and TSR -- there's tons of examples out there of people sheepishly admitting that a letter or article they wrote for Dragon magazine with a studied "adult professional" tone was really written when they were 14 or whatever) but they all thought they were doing something adult -- something above their expected level of intelligence and sophistication, something vaguely dangerous and forbidden. Hell, this dynamic existed within the very Gygax household -- two of the primary playtesters of his "adult" game were his teenage sons -- Ernie in the 70s, Luke in the 80s (and, for that matter, Alex in the 00s).
A big part of the appeal of AD&D for us 80s kids was the difficulty of understanding it -- that you had to be smarter than average to understand it and, once you did, you earned social cachet by explaining it to the other kids (who didn't have their own copies because they couldn't afford them or their parents wouldn't let them, or who had the rulebooks but couldn't make any sense out of them because they didn't understand the Latinate abbreviations and words like "milieu" and "antithesis of weal"). Likewise with the illicit artwork with violence and nudity and pictures of demons and sacrificial altars and stuff -- and the media-panic surrounding it. Sure anybody who had read the books and played the game knew the accusations were all total crap, but it definitely made the game seem "cooler" (and yes, hard as it is to believe nowadays, there was a time -- when I was in 4th-6th grade, so 1984-86 -- when D&D (or, rather, AD&D -- the D&D boxed sets by Moldvay and later Mentzer were the dirty little secret, the way those of us who understood the game had by and large actually learned it, but we'd never admit that openly because that was "kiddie stuff" whereas AD&D was the Real Thing -- just like we'd sure as hell never admit to watching the D&D cartoon or playing with D&D action figures, even though most of us did) was considered cool, where the kid with the biggest collection of stuff and best understanding of the rules (usually because he had an older brother who he'd learned it from, or because he secretly had one of the Basic Sets (see above)) had an "instant in" with the popular (note: middle-school popular, which is different from high-school popular when cars and drugs and sex are involved) crowd).
When TSR started changing the game around -- making it more kid-friendly by simplifying the language and sanitizing the content, actually marketing it towards the age of people who were playing it rather than the age of people those playing it looked up to and wanted to be like -- the appeal was lost, and D&D went from being the cool, dangerous thing that the smart and sophisticated kids played to being the boring thing that nerdy kids play, which is how it's been known ever since. By making D&D into something safe and accessible that anyone could understand and play, it became something nobody wanted to play.
(Originally posted here.)
My only quibble with this post is that, despite being a few years older than Foster, I don’t recall AD&D ever being especially ‘cool’, even during ‘middle-school’ (though it did seem not especially nerdy in the early-mid 1980s).