November 20, 2025 – Forty years ago today, a skinny 30-year-old Bill Gates stood on stage and released something that looked like a toy: Microsoft Windows 1.01 – shipped on five floppy disks and needed a whopping 256 KB of RAM.
Nobody knew it yet, but the world had just changed forever.
That clunky tiled interface, that ridiculous mouse tutorial, that unstoppable ambition – it was the first time millions of people realized computers could be fun, not just for accountants and nerds.
Today, on its exact 40th birthday, Windows is still the king of desktops (over 70% market share), powers more than a billion devices, and is in the middle of its biggest glow-up ever with Copilot+ AI PCs. But damn if it doesn’t make us feel old.
So grab a Monster Energy, put on some mid-2000s emo, and let’s take the most nostalgic, chaotic, loving ride through forty years of the OS that raised us.
1985 – The Day the Start Button Was Born
Bill Gates originally wanted to call it “Interface Manager.”
Thank God marketing stepped in.
Fun fact: Windows 1.0 was so slow that reviewers called it “vaporware.”
Gates shipped it anyway. Legend behavior.
1990-1993 – Windows 3.0 & 3.1: The First Time We All Screamed “YES!”
Windows 3.0 sold 10 million copies in two years – the biggest software launch in history at the time.
Solitaire was installed on every single one.
Microsoft literally taught the world how to use a mouse… and got us addicted to cards.
We all owe our dragging-and-dropping skills to Minesweeper and Hearts.
1995 – The Day the World Stopped: Windows 95
Microsoft paid the Rolling Stones $3 million (some say up to $14 million) to use “Start Me Up.”
They lit the Empire State Building in Windows colors.
People camped outside stores like it was a PlayStation 5 drop.
The startup sound was composed by Brian Eno.
You can still hear it in your dreams.
And yes, Jay Leno was there. Because 1995 was perfect.
2001 – Windows XP: Peak Childhood
Bliss wallpaper.
The green hill in Sonoma County that’s now a vineyard because the photographer sold the land after the photo.
Luna theme.
Pinball.
That startup sound that felt like hope in audio form.
XP ran from 2001 to 2014 officially.
Some of you reading this are still running it in 2025. We see you.
The Villains We Loved to Hate
- Clippy (1997–2003)
“It looks like you’re writing a letter…”
No Clippy, I’m writing a suicide note because you keep popping up.
Yet in 2021 Microsoft brought him back as an emoji.
We pretended to hate it… then set it as our profile pic. Never change, internet.
- Windows ME (2000) – The OS so bad it became a war crime.
Constant crashes, System Restore that forgot how to Restore, blue screens for breakfast.
Still the undisputed champion of “worst Windows ever.” - Windows Vista (2007) – Beautiful, but ate RAM like a starving raccoon.
Aero Glass was gorgeous. UAC was… a lot. - Windows 8 (2012) – Microsoft said “no Start button” and the entire planet revolted.
We have never recovered.
The Blue Screen of Death – Our Shared Trauma
Every 90s/2000s kid has a story.
You’d be in the middle of a 500-word essay typed in WordPerfect, hit one wrong key, and suddenly sad Mac face but worse.
We learned to save every 30 seconds because of this screen.
The Antitrust Trial – When Bill Gates Became a Meme Before Memes Existed
1998–2001: The United States v. Microsoft.
Bill Gates’ deposition video is still comedy gold.
“I don’t recall” 86 times.
The man who memorized license plates couldn’t remember if he said “cut off Netscape’s air supply.”
The Logo Glow-Up Timeline
2025 – Windows Is 40 and Suddenly… Cool Again?
Copilot+ PCs, Recall (yes it’s controversial but also insane), Windows 11 getting actually good with 24H2 and now 25H2 on the way.
Microsoft is putting AI directly into the taskbar. Your PC can literally watch your screen and help you now.
And yeah, some people are mad about the AI stuff (looking at you, The Verge headline today), but let’s be honest – Windows has survived ME, Vista, 8, and the Zune. It’ll survive this too.
Final Thought
Forty years.
From five floppy disks to neural processors.
From “Where do you want to go today?” to “Hey Copilot, fix my life.”
We grew up with Windows.
We cursed it, we loved it, we threw laptops because of it, we met our first love on MSN Messenger because of it.
Happy 40th birthday, you glorious, buggy, beautiful mess.
We wouldn’t trade a single blue screen for anything else.
Start me up. 🎉
Share this if Windows raised you too.
