What we see on our desktop PCs has changed dramatically over the years, and I often reminisce about the good old days of seminal programs and simple interfaces. Here are five programs and features that bring back fond memories and make me feel nostalgic (and old!)

5
Microsoft Money

The advent of online banking was one of the reasons Microsoft ditched Money in June 2009, though it’s fair to say that this wasn’t a like-for-like replacement. Indeed, my online banking apps today could only dream of executing some of the tasks that Microsoft Money could do, like presenting my monetary data in chart form, categorizing spends and setting limits for each category, and generating financial reports.

21st-century alternatives are out there, but, again, they don’t cut the mustard. For example, many people report sync issues and clunky interfaces on some of the more well-known personal finance management apps, and creating your own budget-tracking Excel spreadsheet takes a certain level of expertise.

I’d rejoice at the reintroduction of Microsoft Money, which helped me manage my money as a student, and you only have to look at online forums to see that many others agree. If—and it’s a big if—you can trust Microsoft’s privacy policy, just imagine how powerful Microsoft Money could be today alongside Copilot. It could analyze your income and outgoings, suggest ways to save money, and give you ideas for investments if you’re interested in the stock market.

4
Windows Media Center

Introduced in Windows XP but canceled in 2016, Windows Media Center was a powerful media management tool that allowed us to organize movies, music, and live TV without having to subscribe to dozens of streaming and storage services like we do today.

I remember my disbelief at being able to use Windows Media Center to record my favorite programs. A friend of mine set up a Windows Media Center theater in his basement, and I spent more time there than I did at home!

As with many of the programs and features in this article, Windows Media Center was clean and simple. It was user-friendly, convenient, and could be controlled with a remote, a combination many modern platforms lack. Sometimes, it’s nice to think back to when tech (and life!) was much simpler, and reminiscing about Windows Media Center takes me on a very pleasant trip down memory lane.

3
MSN Messenger

For us 90s kids, very little triggers a greater feeling of technological nostalgia than MSN Messenger. Just seeing the MSN logo reminds me of the screeching tones of dial-up internet (and my mom telling me to get off the computer and do my homework!)

MSN Messenger was one of the first mainstream instant messaging platforms, and, at the time, it felt like a revelation.

I remember my CRT monitor being clogged with multiple MSN windows as I struggled to keep up with the many incoming messages (I used to think this meant I was popular) and video call requests. I also remember appearing offline so that I could strategically see who was online without anyone detecting my presence.

The program’s best feature was its nudge tool, which you could click to get someone’s attention by making their screen wobble.

MSN is the program that most reminds me of a time when things weren’t drowned in a tsunami of social media platforms, and I’d love to spend just a day reliving its functionality and simplicity.

2
Windows Mail and Calendar

Since the start of January 2025, people trying to use the free Windows Mail and Calendar apps have been met with a message telling them that these trusty programs are no longer supported, and that they will be directed to the new Outlook.

I’ll admit that most of the programs and tools I’ve listed in this article have been replaced by upgraded alternatives designed to cope with modern demands. The same could probably have been said for Windows Mail and Calendar if Microsoft had stuck with the classic version of Outlook. But it didn’t, and many people (me included) think that the new Outlook isn’t fit for purpose.

The Windows Mail and Calendar apps did pretty much everything a personal user needed them to do. Windows Mail was simple, allowed you to easily manage multiple email accounts, and offered all the fundamental features without unnecessary clunk.

Similarly, Windows Calendar was simple to use, offered decent offline access, and made organizing your week a trouble-free task. Together, Mail and Calendar were nicely embedded within the Windows operating system and were light on system resources.

I get that things have to move with the times, and maybe Mail and Calendar were too simple to keep up with tech development. However, Microsoft’s inability to offer us a ready-made alternative makes Mail and Calendar’s retirement a little bit more difficult to stomach.

1
Microsoft Clippy

If you don’t remember Microsoft Clippy, it’s probably because you were born too late, and I’m sad for you that you didn’t experience the pleasure of its company.

Clippy was integrated into Microsoft Office for free and would pop up whenever I started a project to ask whether I needed any help. I’m sure many readers will argue that it was an annoying and intrusive anthropomorphic paperclip that hindered more than it helped. However, to me, it was an endearing, memorable tool that sat by my side while I worked, ready to assist me whenever called upon.

Although today’s AI-based alternative, Copilot, encourages you to ask it questions as though it were a human, Clippy had more personality and was truly the layperson’s Microsoft assistant. If I worked for Microsoft, I would have brought back Clippy as the face of Copilot, and I think Microsoft missed a trick by not doing so.

Discontinued apps no longer available from their respective app stores can’t be updated to protect you from vulnerabilities or address performance bugs. So, if you’re craving a shot of nostalgia, dust down your old consoles and sink your teeth into some retro games instead.