Last week we enjoyed looking at Windows 3.1 running in VMware Player on Windows 7.  Today, let’s upgrade our 3.1 to 95, and get a look at how most of us remember Windows from the 90’s.

In this demo, we’re running the first release of Windows 95 (version 4.00.950) in VMware Player 3.0 running on Windows 7 x64.  For fun, we ran the 95 upgrade on the 3.1 virtual machine we built last week.

Windows 95

So let’s get started.  Here’s the first setup screen.  For the record, Windows 95 installed in about 15 minutes or less in VMware in our test.

Strangely, Windows 95 offered several installation choices.  They actually let you choose what extra parts of Windows to install if you wished.  Oh, and who wants to run Windows 95 on your “Portable Computer”?  Most smartphones today are more powerful than the “portable computers” of 95.

Your productivity may vastly increase if you run Windows 95.  Anyone want to switch?


No, I don’t want to restart … I want to use my computer!

Welcome to Windows 95!  Hey, did you know you can launch programs from the Start button?

Our quick spin around Windows 95 reminded us why Windows got such a bad reputation in the ‘90’s for being unstable.  We didn’t even get our test copy fully booted after installation before we saw our first error screen. 

Windows in space … was that the most popular screensaver in Windows 95, or was it just me?

Hello Windows 3.1!  The UI was still outdated in some spots.


Ah, yes, Media Player before it got 101 features to compete with iTunes.


But, you couldn’t even play CDs in Media Player.  Actually, CD player was one program I used almost daily in Windows 95 back in the day.

Want some new programs?  This help file about new programs designed for Windows 95 lists a lot of outdated names in tech. 

 new programs for 95

And, you really may want some programs.  The first edition of Windows 95 didn’t even ship with Internet Explorer.   We’ve still got Minesweeper, though!

My Computer had really limited functionality, and by default opened everything in a new window.  Double click on C:, and it opens in a new window.  Ugh.

But Explorer is a bit more like more modern versions.

Hey, look, Start menu search!  If only it found the files you were looking for…


Now I’m feeling old … this shutdown screen brought back so many memories … of shutdowns that wouldn’t shut down!

But, you still have to turn off your computer.  I wonder how many old monitors had these words burned into them?

So there’s yet another trip down Windows memory lane.  Most of us can remember using Windows 95, so let us know your favorite (or worst) memory of it!  At least we can all be thankful for our modern computers and operating systems today, right? 

Matthew Guay
Matthew Guay is a veteran app reviewer and technology tip writer. His work has appeared on Zapier's blog, AppStorm, Envato Tuts+, and his own blog, Techinch.
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