I think, in many ways, D&D is a reflection of the larger/broader culture from which it spawned and has been continually reiterated by/within.
At its dawning, the Saturday afternoon kung-fu movies of the day gave us a Monk class. A resurrgent interest in Tolkien's work -thanks to a few different animated films or tv specials- put Aragorn front and center, leading to a player who wanted to play an "Aragorn," bringing us the Ranger class. The Tolkien species/race options are apparent.
Lovecraft and Moorcock, Vance and Anderson, et al. Gygax & Arneson's literary influences are well documented and shaped their conceptions of how the game would be formed.
Joseph Campbell's Hero with a Thousand Faces (1949) and subsequent work coming into the common discourse with The Hero's Journey and Power of Myth ('87 and '88 respectively) clearly influenced both designers, writers, and players of BECMI, AD&D 1e, and probably 2e.
Disney released The Sword in the Stone in '63. The Rankin-Bass Hobbit in '77 and Return of the King in '80. With the Bakshi psychedelic masterpiece "Lord of the Rings" sandwiched in '78. The Last Unicorn came in '82. The Black Cauldron was '85 (arguably during 1e's hay day, and the Satanic Panic) but may have influenced development for 2e.
The D&D Saturday morning cartoon, of course, influenced and/or was influenced by the release of Unearthed Arcana, adding Barbarian, Cavalier, and Acrobat (as well as numerous additional rules options, spells and magic items) to the game.
The '80s success of the Schwarzenager Conan films can not be ignored. Excalibur! Legend. Time Bandits. The Neverending Story. The Dark Crystal. Fantasy -specifically heroic adventure fantasy- was having a clear and GLORIOUS moment.
The Dragonlance original trilogy, a proud derivative, cemented AD&D's early successes and set a tone and mood for 2e, with their publications in '84, spring and fall of '85. Their second trilogy -throughout '86- enjoyed continuing success.
With the '80s coming to their end, a new edition (following over a decade of D&D and AD&D) must have made some sense. It was the changing of an era. Society -or so we thought- was beginning to make some (slow and long overdue) changes. With 2e's release in '89, and BECM being compiled into the Rules Cyclopedia in '91, D&D was ahead of the game, as it were.
There was some...organizing...and reorganizing. An attempt to codify certain things further than AD&D had done. A good deal of streamlining. Organizing the multiple different Monster books into a single binder where you could access everything. Simplifying the class list (to not include Unearthed Arcanaa bit of restructuring - we lose the Monk in the PHB. Bard becomes a "Rogue" category class with the Thief. Mages get specialists (including the original, Illusionist) but widely open wizard-type options. The introduction of Clerical "spheres" for deities and spells begins a long, and ongoing, broadening of Clerical archetype from the healers to the battle-priests (but NOT the same as a Paladin. No no

to the nature guardian Druid types.
D&D changes hands from TSR to WotC and 3e is born at another moment of pivotal societal change, the new millenium. Computers have become ubiquitous. There is, particularly among the "nerd-/geek-dom" to which most D&D gamers were prescribed, are generally video gamers as well. Computer programming is becoming something of a "hobby" even for those that don't take it on as a profession.
The...."exacting" nature of coding begins to become a societal "view" or expectation. So we get a game that is VERY detailed. A system for all contingencies...just like a computer program. If you don't put it in there, the program won't be able to "understand" your commands or do what you want it to.
So 3e gets granular...and then microscopic... in its exacting completeness. Everything -combat, saves, spell casting, skills- gets broken up into component parts, +1s that add and add and add to make you more powerful. Class archetpyes are split off and split off and split off again into ever-narrowing slices of fantasy-adventurer flavors...and/or directly ripped out of other media -films, comic books ('90s Psylocke is lookin' at you, Soulknife), tv- to be turned into versions for a D&D character.
We also see, I feel, we begin to see the creeping growth of an expectation of "winning." Of D&D being a game that you can "beat." That the monsters and challenges MUST by conquerable by the players.
Coming toward the end of that decade, technology is taking leaps and bounds in availability...AND, notably, getting smaller and smaller and thinner and flatter and (allegedly) easier and easier to access. Makes sense then, that 2008's 4e is an attempt to do all of that with what had become 3.x's MASSIVE sprawling system of options upon options upon options upon options...you get the idea.
4e is going to be as easy to play and accessible to -not just RPGers, not just D&D's loyal fandom- but ALL of geek-dom and young people as a video game. Streamlined, streamlined,and streamlined some more...to literally play, at the table, like an MMO. Characters have set powers and suites of selectable options that are very carefully pruned and shaped to create a particular flavor of character. The "winnable D&D, PCs just fight-and can automatically defeat- and move on to the next reward" attitudes begun in 3e have become ubiquitous as a culture of immediate gratification (internet) and pure lack of consequences (everyone gets a trophy for showing up) has seeped, quite pervasively, into the societal zeitgeist... so, not surprisingly, found among D&D gamers (who are almsot certainly also video gamers and/or playing their RPG games online).
Thankfully, from my perspective, that version of D&D does not succeed/last for a full decade and 5e releases in 2014.
Much has been written about 5e's desired design aesthetic of "returning" to some of D&D's origins, while maintaining a robust -but not persnickety or overly granular as the 3.x's- rules set. What would people suppose were the pervading cultural elements -aside from 4e's apparent monetary failures- that might have contributed to this change of direction and tone and preferences for 5e?