Microsoft turns 50: These are its 10 best moments (and 5 of its worst)

Microsoft is celebrating its 50th anniversary by highlighting Copilot, its AI assistant now deeply integrated into Windows and Office. It’s a fitting milestone for a company that began by simplifying computing and continues to do so through artificial intelligence. As we reflect on its legacy, these are Microsoft’s 10 most iconic moments—and 5 it might rather forget.

The best moments from Microsoft’s history

Windows 95 introduced the Start button and taskbar, shaping how billions would interact with their PCs. Its launch defined a generation of computing.

In 1997, Microsoft invested $150 million in Apple, helping save its rival from collapse and ensuring the survival of what would become the iPhone-maker.

Halo’s debut on Xbox redefined gaming exclusivity, cementing Microsoft as a serious player in the console world.

Clippy, though divisive, became a pop culture icon, symbolizing Microsoft Office for an entire generation.

The Metro design language influenced interface aesthetics, with Windows Phone and Xbox 360 showcasing this bold, tile-based UI.

Forza Horizon 5 has pushed the boundaries of open-world racing, delivering one of the most beloved modern Xbox experiences.

Xbox 360’s lavish launch events helped build cultural cachet, drawing celebrities and fans alike.

3D Pinball in Windows 95’s Plus! pack became a nostalgic classic, beloved by countless users for its digital arcade charm.

Windows Hello transformed PC security, using biometrics to simplify and secure the login process.

And finally, Steve Ballmer’s viral “Developers!” moment remains an unforgettable image of unfiltered tech enthusiasm.

The worst moments Microsoft would rather forget

Windows Vista frustrated users with performance issues, setting back adoption for years.

The Kin phones lasted just weeks on the market, a quick failure in the smartphone space.

The Xbox One reveal focused too much on TV, alienating core gamers.

Windows RT confused users with software limitations, leading to commercial failure.

And Internet Explorer’s decline into obsolescence ended in a quiet farewell in 2022.