INTERNETHISTORYCHAOS

The Internet's
Greatest Moments

A Timeline of Digital Chaos

From the Space Jam website (1996, still live) to Gangnam Style breaking YouTube's view counter to ChatGPT hitting 100 million users in two months. Every iconic internet moment, meme, and event — with commentary from a guy who lived through all of it and is now using an AI to write about it. The irony is not lost on me.

30 Years of Beautiful Chaos

The internet went from “cool, I can email my cousin” to “an AI just generated a fake video of the Pope in a puffer jacket” in about 30 years. That's not a lot of time for that much change. We went from dial-up modems to AI coding agents and most of us are still processing it.

I got my first email address in the late 90s. I remember AIM away messages, the sound of dial-up connecting, and waiting three minutes for a single image to load. Now I argue with an AI about TypeScript errors at 2am and it builds me a website with 960 pages. The trajectory is insane if you stop and think about it. So I stopped and thought about it. This is the result.

30+

Years Covered

1996 to 2025

Moments

that shaped the internet

5.4B

People Online

as of 2025

Site Still Live

spacejam.com, baby

The Timeline

24 moments that made the internet what it is. For better or worse.

1996

Space Jam website goes live

Warner Bros. built spacejam.com in 1996 to promote the movie. Tiled backgrounds. Tiny GIFs. Centered tables. They never took it down. It's STILL LIVE. Go check right now — spacejam.com. It's the most beautiful time capsule on the internet. Read the full Space Jam tribute. Every web developer should be required to visit spacejam.com once a year as a humility exercise.

1998

Google launches from a Stanford dorm room

Larry Page and Sergey Brin built a search engine in a garage. Their first server was made of Lego. LEGO. The company that now controls what most of humanity sees on the internet started with a toy brick server rack. They almost sold it for $1 million in 1999. The buyer said no. That buyer thinks about this every single day.

1999

Napster launches. Music industry has a heart attack.

Shawn Fanning was 18 years old when he built Napster. Eighteen. He single-handedly panicked an entire industry. 80 million users at its peak. The music industry sued a teenager and won, but the damage was done — the idea that music could be free was out there and you can't un-ring that bell. Spotify exists because of Napster.

2003

MySpace launches. Tom is everyone's first friend.

Tom Anderson was literally everyone's first friend on the internet. He had that one photo — the white t-shirt, the slight smile, the whiteboard behind him. MySpace taught an entire generation how to customize CSS (badly), how to auto-play music on your profile (crimes against humanity), and how to rank your Top 8 friends (the most stressful social exercise of the 2000s).

2004

Facebook launches from a Harvard dorm

Mark Zuckerberg built a website for rating people's attractiveness and it turned into a $900 billion company. The early days of Facebook were magical — you needed a .edu email, it was just college kids, and poking people was a feature. Now your aunt shares minion memes on it. We didn't know how good we had it.

2005

YouTube uploads its first video ("Me at the zoo")

Jawed Karim stood in front of elephants at the San Diego Zoo and said "and the cool thing about these guys is that they have really, really long trunks." That's it. That's the first YouTube video ever. 19 seconds that launched a platform with 800 million videos. The elephants had no idea they were making history.

2006

Twitter launches. Nobody knows why.

Jack Dorsey's first tweet: "just setting up my twttr." 140 characters. No images. No threads. No quote tweets. No main character of the day. It was just people posting what they had for lunch. We had no idea it would become the town square of the internet. Or that it would be sold to Elon Musk and renamed X. Nobody saw any of this coming.

2007

iPhone announced. Steve Jobs casually changes everything.

Steve Jobs walked on stage and said "today Apple is going to reinvent the phone" and everyone thought he was being dramatic. He wasn't. He was underselling it. The iPhone didn't just change phones — it changed cameras, maps, music, banking, dating, and basically every other aspect of human existence. The crowd reaction when he scrolled with his finger is still incredible to watch.

2008

Obama "Hope" poster goes viral

Shepard Fairey's poster of Barack Obama became the most iconic political image of the 21st century. It wasn't commissioned by the campaign — Fairey just made it. A street artist made a poster that helped elect a president. The internet made that possible. Try doing that with a pamphlet.

2009

Bitcoin whitepaper circulates. $0.00 per coin.

Satoshi Nakamoto (whoever that is) published a paper about digital money and disappeared. Bitcoin was worth literally nothing. You could've bought thousands of them for the cost of a pizza. Someone actually did — they paid 10,000 BTC for two Papa John's pizzas. I'm not a crypto guy (at all) but the irony of that pizza transaction is objectively funny. Those pizzas would be worth hundreds of millions today.

2010

Old Spice "The Man Your Man Could Smell Like"

Isaiah Mustafa walked out of a shower, onto a boat, onto a horse, in one continuous shot and created the template for every internet ad that came after. This commercial turned Old Spice from "what your grandpa wears" to "actually kind of cool." They responded to fans on YouTube in real-time. It was the first time a brand actually understood the internet.

2012

Gangnam Style breaks YouTube's view counter

PSY made a song about a neighborhood in Seoul and it got so many views that YouTube had to upgrade their view counter from a 32-bit integer. The platform literally could not count high enough. 2.1 billion views before YouTube even had a system that could handle numbers that big. The song is silly. The dancing is silly. None of it should work. It worked so hard it broke the infrastructure.

2013

Doge meme. wow. such internet. very meme.

A Shiba Inu named Kabosu became the most recognized dog on the internet. Comic Sans text in broken English around a confused-looking dog. That's the whole format. It spawned a cryptocurrency worth billions (don't get me started), inspired 10,000 imitators, and the original Doge photo is now an NFT. The dog had no idea. The dog was just sitting there.

2014

Ice Bucket Challenge raises $115M for ALS

People dumped ice water on their heads, posted it online, and donated money to ALS research. It raised $115 million. That's more than most charities raise in a decade. The internet decided to do something genuinely good for once and it actually worked. The research it funded contributed to a real breakthrough in understanding the disease. Sometimes the internet gets it right.

2015

The Dress. Blue/black or white/gold?

A single photo of a dress broke the internet harder than anything before or since. People genuinely could not agree on what color it was. Families were torn apart. Coworkers stopped speaking. Neuroscientists wrote papers about it. The answer is blue and black. If you see white and gold, your brain is lying to you and I'm sorry. It's blue and black.

2016

Harambe. That's it. That's the entry.

A gorilla at the Cincinnati Zoo became the biggest meme of 2016. I'm not going to explain the whole thing. If you know, you know. If you don't, just trust me that a gorilla became one of the most referenced cultural figures of the decade. The internet mourned Harambe harder than most historical figures. "Take your d— out" became a thing people said in public. 2016 was a different time.

2017

Fyre Festival. The cheese sandwich heard round the world.

Billy McFarland promised a luxury music festival in the Bahamas. Influencers promoted it. People paid thousands. They got disaster relief tents and cheese sandwiches. The photo of that cheese sandwich — two slices of bread, a slice of cheese, and some lettuce in a styrofoam container — is the most important image in the history of consumer fraud. Read the full Fyre Festival timeline. Two documentaries were made about it. Both are excellent.

2019

Area 51 raid meme. 2M RSVP. 150 show up.

Someone made a Facebook event called "Storm Area 51, They Can't Stop All of Us." Two million people clicked "Going." The US Air Force had to issue an official warning. On the actual date, about 150 people showed up to the desert, stood around awkwardly, took some photos, and went home. The gap between internet enthusiasm and real-world commitment has never been more perfectly illustrated.

2020

Tiger King. Everyone watched Tiger King.

The entire world was locked inside during a pandemic and collectively decided to watch a documentary about a man who kept tigers, tried to hire a hitman, and ran for president. Joe Exotic became a household name. Carole Baskin became a household name. 64 million people watched it in the first month. The internet had nothing else to do and it showed.

2021

GameStop / WallStreetBets short squeeze

Reddit's r/WallStreetBets noticed that hedge funds had shorted GameStop's stock more than 100%. So they bought it. All of it. The stock went from $17 to $483. Hedge funds lost billions. A guy named Keith Gill ("Roaring Kitty") became a folk hero. Robinhood stopped people from buying, Congress held hearings, and for one brief, beautiful moment, the internet beat Wall Street. Then Wall Street adapted. But for that one week? Chef's kiss.

2022

ChatGPT launches. Everything changes.

OpenAI released ChatGPT on November 30, 2022 and hit 100 million users in two months — the fastest-growing consumer app in history. Everyone had the same reaction: "Wait, it can DO that?" followed by "Wait, is my job safe?" We're still working through both of those questions. AI went from science fiction to your coworker overnight.

2023

Threads launches. Twitter becomes X. Nobody's happy.

Meta launched Threads, a Twitter competitor, and got 100 million signups in five days. Then everyone stopped using it. Meanwhile, Elon Musk renamed Twitter to X, removed the blue checks, and added a subscription tier. The bird logo that everyone recognized for 17 years was gone. Nobody was happy about any of this. We're still not happy.

2024

AI slop floods the internet

AI-generated content hit critical mass. Facebook got flooded with AI images of Jesus holding shrimp. Google Search started serving AI answers that told people to eat rocks. Deepfakes got good enough to fool most people. The internet entered its "we can't tell what's real" era, which is either terrifying or hilarious depending on your personality type. I choose hilarious because the alternative is too depressing.

2025

Claude Code builds websites while you sleep

I'm going to break the fourth wall here. This very page — the one you're reading right now — was built with Claude Code, Anthropic's AI coding agent. This entire website has 960+ pages and most of them were built by an AI that I argue with at 2am about TypeScript errors. We've reached the point where an AI is writing a timeline of the internet's greatest moments ON the internet. We're so meta it hurts. The future is weird and I'm here for it.

Glen's Take

I've been on the internet since the late 90s. I remember when “going online” was an event — you'd sit down, connect to dial-up, and you had maybe 30 minutes before someone needed the phone. Every webpage felt like a discovery. AltaVista was the search engine. AIM was the social network. And if you wanted to know something, you didn't Google it. You asked Jeeves.

Now I'm sitting here in 2026 using Claude Code — an AI coding agent made by Anthropic — to build a 960-page website that includes a shrine to Space Jam, ranked lists of billionaires, and this very timeline you're reading. The AI and I argue about TypeScript errors. We disagree about import paths. Sometimes it tries to use framer-motion instead of motion/react and I have to correct it. It's like having a very fast, very opinionated coworker who never sleeps.

If you told 10-year-old me — the one waiting for spacejam.com to load on dial-up — that in 25 years I'd be arguing with an artificial intelligence about how to build a website, he would've believed you. Because that kid watched a movie about Michael Jordan playing basketball with cartoon aliens and thought, “yeah, the future is going to be weird.”

He was right.

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Frequently Asked Questions

What's the greatest internet moment of all time?

The GameStop short squeeze. No contest. The internet — specifically a subreddit full of self-described degenerates — took on billion-dollar hedge funds and WON. For one week. Hedge funds lost billions, a regular guy became a folk hero, and Congress held hearings because people bought stock they liked. That's the internet at its peak: chaotic, hilarious, and genuinely consequential.

Is spacejam.com really still live?

Yes. Go check. spacejam.com. It's been live since 1996 and Warner Bros. has never taken it down. It's the oldest continuously live movie website on the internet and it's absolutely beautiful in its 90s web design glory. Tiled backgrounds. Centered tables. Tiny GIFs. It's perfect.

Was the Ice Bucket Challenge actually effective?

Incredibly effective. It raised $115 million for ALS research in about 8 weeks. That funding contributed to the discovery of a gene — NEK1 — that's linked to ALS. So yes, pouring ice water on your head and posting it online actually advanced medical science. The internet did something genuinely good and it worked. That's rare.

Is Glen anti-crypto?

Deeply. I'm not going to tell you what to do with your money, but I will tell you that I put mine in GSE preferred stock, which has been in conservatorship since 2008. So I'm not exactly in a position to give investment advice. But I will note that the 10,000 BTC pizza transaction is objectively hilarious regardless of your opinion on crypto.

Did Claude Code really build this page?

Yes. This entire website — 960+ pages — was primarily built by Claude Code, Anthropic's AI coding agent. I tell it what to build, we argue about TypeScript errors, and eventually a page appears. It's like having a very fast, very opinionated coworker who never sleeps and occasionally needs to be told that 'motion/react' is not the same as 'framer-motion.' We have a complicated relationship.

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