15 Classic Microsoft Products You Forgot Existed—Until Microsoft’s 50th Anniversary Brought Them Back to Mind
Microsoft has created some legendary products over the years, but many of them have faded into obscurity—until now.
- Sophia Zapanta
- 5 min read
As Microsoft hits the big 5-0, nostalgia kicks in and reminds us of forgotten products that once shaped our digital lives. From clunky yet charming software to ahead-of-its-time gadgets, these relics prove that Microsoft was always pushing boundaries. Some were brilliant, some were bizarre, but all of them deserve a moment in the spotlight.
1. Microsoft Bob
microsoft on Wikimedia Commons
Microsoft thought computers needed a friendly face, so they gave us Bob, a cartoonish interface meant to simplify Windows. Instead of being helpful, it confused users with its overly cute design and talking dog assistant. It flopped so hard that Microsoft buried it, but tech historians still whisper its name. Bob was a good idea trapped in a bad execution, and for that, it’s unforgettable.
2. Zune
Bkwparadox on Wikimedia Commons
Microsoft’s answer to the iPod was sleek, ambitious, and tragically late to the party. The Zune had great sound quality and even let users share songs wirelessly, but Apple had already won the music war. Despite a cult following, it was discontinued, leaving behind a legacy of “what could have been.” Now, it’s a collector’s item for tech nostalgists who refuse to let go.
3. Clippy
David Revoy on Wikimedia Commons
The paperclip assistant that lived to annoy anyone using Microsoft Office in the late ‘90s and early 2000s. Clippy meant well, but its constant pop-ups and unhelpful advice made it more of a pest than a pal. Microsoft finally retired it, but its meme-worthy reputation lives on. Love it or hate it, you’ll never forget Clippy’s wide-eyed stare.
4. MSN Messenger
Bent52 on Wikimedia Commons
Before WhatsApp and Discord, there was MSN Messenger, the king of instant messaging. It had everything—custom emojis, dramatic “nudge” alerts, and the ability to log in to appear offline. Friendships were built on those chat windows, and heartbreaks played out through song lyrics in statuses. When it shut down, a whole generation lost their favorite online hangout.
5. Encarta Encyclopedia
Microsoft on Wikimedia Commons
Before Wikipedia, students relied on Encarta, Microsoft’s digital encyclopedia packed with multimedia and interactive articles. It was a lifesaver for last-minute homework but struggled once the internet made information free. Microsoft retired it in 2009, officially surrendering to the power of crowdsourced knowledge. Now, it’s just a nostalgic reminder of CD-ROM research marathons.
6. Windows Phone
Microsoft Sweden on Wikimedia Commons
Microsoft tried to take on Apple and Android with a fresh, tile-based interface that was actually pretty good. The problem? Developers weren’t interested in making apps for it, and users weren’t interested in buying it. Despite its slick design, the Windows Phone became one of Microsoft’s biggest hardware flops. Today, it’s a footnote in smartphone history.
7. Microsoft Kin
Evan-Amos on Wikimedia Commons
Imagine a phone that was supposed to be cool and social but ended up being neither. That was the Kin, Microsoft’s ill-fated attempt at a teen-friendly mobile device. It lasted only 48 days before Microsoft pulled the plug, making it one of the fastest product failures ever. If you blinked in 2010, you probably missed it entirely.
8. Microsoft Works
HilldeFirst on Wikimedia Commons
A budget-friendly alternative to Microsoft Office, Works was like Word and Excel’s less capable cousin. It came pre-installed on many PCs, making it a go-to for simple documents and spreadsheets. Unfortunately, it lacked the power of Office and slowly faded into irrelevance. Microsoft finally discontinued it, admitting that most people needed more than just the “Works.”
9. Flight Simulator (Classic Versions)
Mchendrix2023 on Wikimedia Commons
Before modern versions wowed gamers, the original Microsoft Flight Simulator was the ultimate test of patience and skill. The graphics were blocky, and the controls were complex, but it gave aviation fans a taste of the skies. The franchise went quiet for years before Microsoft revived it with a stunning new version. Old-school fans still remember the challenge of landing a pixelated 747 in stormy weather.
10. Microsoft XPS Viewer
Tom Page on Wikimedia Commons
Microsoft thought it could replace PDFs with XPS files, but the world said, “Nah, we’re good.” The XPS format was supposed to be the future of document sharing, but almost nobody used it. Even Microsoft lost interest, slowly phasing it out in later Windows versions. Today, XPS is the forgotten file format that nobody asked for.
11. Internet Explorer
Vulphere on Wikimedia Commons
For years, Internet Explorer was the way to browse the web until it became a slow, outdated joke. Microsoft tried to keep it relevant, but Chrome and Firefox ate its lunch. Eventually, Microsoft put it out of its misery and introduced Edge as its replacement. Even now, old-school users still remember the days of endless pop-ups and “Not Responding” messages.
12. Microsoft Money
Microsoft on Wikimedia Commons
Before online banking was everywhere, Microsoft Money helped users track their finances with a digital checkbook. It was useful, but its days were numbered when banks started offering better tools for free. Microsoft quietly discontinued it, letting Quicken and other finance apps take over. Now, it’s a relic from an era when budgeting required a CD-ROM.
13. Microsoft SideWinder
WolfenSilva on Wikimedia Commons
Microsoft once made gaming hardware, and the SideWinder controllers were ahead of their time. These were joysticks and gamepads built for serious PC gamers, with customizable buttons and force feedback. They were great, but Microsoft eventually left gaming peripherals to companies like Razer and Logitech. Today, SideWinder controllers are rare finds for retro gaming collectors.
14. Microsoft Cortana (Consumer Version)
The Microsoft Corporation Wikimedia Commons
Cortana was Microsoft’s AI assistant, meant to compete with Siri and Alexa, but it never quite caught on. It worked well for reminders and searches but lacked the charm and usefulness of its competitors. Microsoft slowly pulled it from the consumer market, shifting Cortana to business-focused tasks instead. Now, it’s just another AI experiment that didn’t stick.
15. Microsoft Tag
Microsoft on Wikimedia Commons
Microsoft thought QR codes needed an upgrade, so they created Tag, a colorful, high-tech alternative. It was supposed to revolutionize mobile scanning, but QR codes became the standard instead. Microsoft shut it down, leaving it as another ambitious but unnecessary experiment. If you ever scanned a Tag, consider yourself part of a very exclusive club.