Microsoft turns 50 with the best memes we can all relate to


As Microsoft is turning 50, and while it would be tempting to create a meme for each of its 50 years, that’s a task even Copilot would find daunting; after all, Internet memes didn’t exist 50 years ago, right?

Instead, I’ve gathered some of my favorite memes, along with picks from the Windows Central staff. Narrowing them down wasn’t easy, given the sheer volume of great ones out there (and seriously, can we please normalize 16:9 ratio memes going into 2025?).

Microsoft memes are universally understood because most of us working class folk spend a good chunk of our lives staring at Windows screens, and that’s just Windows Update…

Poking fun at these tools of our corporate overlords is a collective coping mechanism, and generally something people from all walks of life understand. But anyway, less talk, more memes!

Learning to count, the Microsoft way…

Counting operating systems with style. (Image credit: Cyanide and Happiness)

Microsoft’s idea of counting has always been avant-garde. Windows 95, 98, and 2000 were named as such after their release years, but hey, XP and Windows Vista sounded new and fancy.

Of course, everyone hated Vista, so Windows 7 was a carefully crafted do-over, a clean slate to win back our trust. And then… they just skipped 9 altogether, reportedly to avoid older software mistaking it for 95 or 98.

What will Windows 12 be called? Probably… erm… Windows 12. Sometimes, they keep us guessing, and sometimes, they don’t.

Security so good even you won’t get into your settings

You shall not pass! (Image credit: Reddit)

Windows Defender, the security system so good, the only thing it defends your PC from is you.

When Microsoft Edge got… Edgy

This is not a real tweet, we repeat, it’s not a real tweet. (Image credit: X/Twitter)

As funny as it would be if Microsoft actually tweeted this, it’s completely fabricated but is regularly shared as something that actually happened. Browser competitor OperaGX is the culprit.

You want to shutdown? That’s the fun part, you can’t.

Messages seen before madness (Image credit: Reddit)

Few things are as inevitable as death, taxes, and Windows updates. Especially when you just want to shut down your laptop and go to bed.

Apple rehashing Microsoft tech and being applauded for it

Apple reinventing the wheel, or rather everyone elses technology. (Image credit: Hijinks Ensue/Joel Watson (2012))

“Who needs a keyboard for a tablet?” the Internet mocked Microsoft for coming up with a keyboard for the Surface back in 2012, resulting in the above comic from Joel Watson on how Apple would inevitably repackage the idea to a more receptive audience.

They did, just three years later.

The true test of a millenial…

This is why I needed glasses as a child (Image credit: Reddit)

We say YouTube Shorts and TikTok are rotting our children’s brains, but really, were we any better staring at the Windows Media Player after school?

Developers, Developers, Developers

Steve Ballmer at NET Conference going crazy about Developers! | 1999 – YouTube
Steve Ballmer at NET Conference going crazy about Developers! | 1999 - YouTube


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