Just verbal diarrhea a bunch of music/pop culture/politics stuff that YOU remember from these eras, or that you perceive as having been popular.
And also correct mine if you think it's wrong somehow. I left a lot blank because I stopped paying attention to pop culture around 2015ish
1996-2000:
pokemon, CDs, walkmans, Goosebumps, backstreetboys, nsync, britney spears, eminem, nickelodeon, y2k, dotcom bubble, Blade, The Matrix, Monica Lewinsky, hanging chads, spongebob
2001-2005:
9/11, iraq war, afghanistan, ipods, 50 cent, DVDs, smash bros. melee, xbox, Halo
2006-2010:
housing crash, Obama, Ron Paul, Taylor Swift/Kanye (both them getting popular and the VMA debacle),
2011-2015:
"birtherism"/Trump, 2012 Mayan prophecy, Vine, Twitter, Trump getting popular around 2015
2016-2020:
2021-now:
1996-2000: Internet Piracy, Nintendo 64, Playstation, Video Game Violence debates, Couch multiplayer, Yo-Yos, POGS, Pixar, Bosnia/Balkins, Saddam Hussein bombing/gassing Kurds, Dr. Dre, "Boomer Shooter" era, Half-Life + CounterStrike, Starcraft, Microsoft anti-trust, , Rap War + deaths + PARENTAL ADVISORY, Pulp Fiction, Star Wars re-relaseased in theaters, LEELO DALLAS MULTIPASS! (The Fifth Element), email takes off, cell phones, pagers, Columbine
2001-2005: Enron (Era of corporate accounting scandals), terrorism,
, terrorism, Lord of the Rings, Harry Potter, terrorism, Jason Bourne movies, Kill Bill, Star Wars Prequels, Spiderman + XMen trilogy, Google (and Gmail), Amazon, eBay, Paypal, Myspace, Razr phone (the "hip" feature phone era), BitTorrent, Michael Moore, School Shooters become a regular thing
FrenchFreedom Fries/Toast/etc, Christian revivalist wave, New Atheism wave, terrorism, Eminem and his endless lawsuits, Apple renaissance (return of Jobs, iPod, iMac, etc), Playstation 2 golden age, LAN parties, MTG, Arena shooters overtake Boomer Shooters, terrorism, Quake III or Unreal game engine dominance, early 4chan, Web 2.0, color-coded terrorist threat warnings, ebaumsworld + Newgrounds for flash games, IRC+AIM+MSN+ASL, hangover from Dot-Bomb era leaving the stock market stagnant -> triggering start of housing bubble,2006-2010: George Bush backlash, Iraq war coverage fatigue, HOPE
, first presidential run for 
, Sarah "Mavricky!" Palin, The Tea Party, Hurricane Katrina, Brown Bloom era of Video Games, Facebook, Youtube, Digg, WHO IS THIS 4CHAN GUY?!, Anonymous' first protest IRL against Scientology, Nintendo Wii + DS prints Nintendo money, 300 movie (and the rise of Snyder), beginning of the Marvel Cinematic Universe, Disney busy Pixar and Marvel, prestige TV like Breaking Bad, iPhone and the dawn of the Smartphone era, Anime + Manga begin to break into mainstream culture, An Inconvenient Truth, Avatar, Christopher Nolen's Batman, Bitcoin first released
2011-2015: Disney buys Lucasfilm, Game of Thrones, Obama disenchantment, Occupy Wall Street + Crackdown, Arab Spring + Crackdown,
, Romney's binders of women, Epic Rap Battles of History, Youtube becomes a global phenomenon, Hipsters, Bacon, Coffee, Rave music revival, Iraq deteriorates and ISIS begins, Instagram, Snapchat, Reddit, Facebook crushes any competition, Marijuana legalization, Tech "Unicorns" (worth over $1 billion) and ramping up of Venture Capital, iPhone and Android push out feature phones, Cloud computing, Anonymous hacking everybody (lulzSec) and its resulting 
mop-up, 4chan's /pol/, GamerGate, Ferguson + BLM protests, Snowden leaks, bitcoin jumps from a few cents to hundreds of dollars
2016-2020:
era, Charlottesville, ISIS, Alt-Right, Wojak + Pepe memes escape containment (meme wars), Monopoly Tech reaches its zenith, Drones, Epstein spotlight, #MeToo, COVID, Star Wars sequels (and other stuff too), Dakota Access Pipeline protests, cryptotokens, r/cth banned
2021-now:
Damn I didn't know Marjorie Taylor Green was well known in the early 00s
excellent job
I feel like there's more we could write for the 2016 era but I'm guessing your as old or older than I am, so you kinda lose track
Yeah I'm old. My Super Nintendo is turning 31 👴
2016+ was definitely a blur, which is why I handwave it under
Era. Its hard to pull that out when it took over so much of the zeitgeist. If anything, I think the previous entries are longer because politics were orderly/boring day-to-day so stuff stood out.
I'd put Hamilton and #Resistance cringe under the 2016- era, specifically the very beginning of
's term.
1996-2000 and early 2000s: Final Fantasy, nu-metal, Napster, wrestling, South Park, Titanic, Fight Club
2001-2005 and continuing into 2006-2010: emo, metalcore, Something Awful (beginning of many future internet trends including memes and 4chan), Guitar Hero and Rock Band, Snakes on a Plane (beginning of corporate internet meme monetization attempts), Angry Nintendo/Video Game Nerd, Cracked.com, Call of Duty (first game was already popular but Modern Warfare was what really launched the series into the stratosphere), FarmVille, Mythbusters, World of Warcraft, Michael Bay's Transformers, Twilight
2011-2015: Hunger Games, Frozen, Flappy Bird, decline of physical media starts, Netflix and Steam start to get popular, rise of indie games, Gangnam Style foreshadows the future rise of K-pop in the West, Mad Max: Fury Road