For fun, I've applied Spengler's cyclical civilization model to web technology. I don't know what to make of it, but there could be some nuggets in the bogus.
Intuition, powerful cultural creation from awakening souls, unity and abundance.
Birth of a grand myth signifying a new conception of God. Fear and longing for the world.
HTML 2.0, Netscape, <blink>, screen-scraping, "Cyberspace!", jodi.org, Flash intros, Perl
Earliest metaphysical organization of the world. High scholasticism.
C2 Wiki, dmoz
Maturing consciousness. Earliest urban-civil society and critical thought.
Reformation: revolt of the religious moderates against the early religion.
CSS, HTML 4, XHTML, HTTP 1.1
Beginnings of a purely philosophical movement. Contrasting idealistic and realistic systems.
A List Apart, Jakob Nielsen
Mathematical breakthroughs leading to a new conception of the world.
RSS, XML, early web frameworks, Flash sites
Rationalism. The depletion of mysticism from religion.
"This is not like in Neuromancer.", Python
Urban rise. High point of disciplined organizational strength.
Faith in the omnipotence of rationality. Cult of Nature.
XHTML 2.0, Atom, high-CSS, Flash used for audio-in and storage
The height of mathematical thought.
high-REST, continuation-based servers, CLOS in ruby-colored straightjacket
The last idealists. Theories of knowledge and logic.
Coming fissure in the world-urban civilization. Exhaustion of mental organization strength. Irreligioussness rises.
Materialism: Cults of science, utility, and luck.
Ajax, Ruby on Rails, microstartupism
Ethical-social ideals: philosophy without mathematics, skepticism.
del.icio.us, reddit, microformats, JSON-APIs
The last mathematical thinkers.
Google architecture, Pugs
Decline of abstract thinkers, and the rise of specialized academic philosophy.
digg, "Ruby is a butterfly"
Spread of the last ideas.