Here is an interesting little trick to get Windows 95 running on your PSP. This is totally for novelty purpose’s though being it runs way too slow to actually be functional. First off you’re PSP is going to have to be running custom firmware, if it’s not you can check out my guide on how to load it here. Next you’re going to need to download a couple files. One program that is required is called DosBox, which is a dos emulator that was ported to the PSP, you can download that file here. The next file you will need is a modified image of Windows 95 with a few preloaded PSP drivers, which you can download here.
Next connect your PSP to your computer and toggle the USB mode. In my computer open up your memory stick drive and navigate to PSP\GAME folder. Unzip the DosBox program and open up the folder. Inside the unzipped folder you should see a folder that says PSP, open that folder as well as the GAME folder. Now take the DosBox program folder that was inside the GAME folder and copy it in to the GAME folder on your memory stick. Next unzip the Win95 file, you should see a file called win95.img after you’ve unzipped. Drag that file in to the DosBox folder on your memory stick. After you’ve transferred the required files you can toggle off the usb mode and load up the DosBox program from your memory stick on your PSP. After the program loads you should see this screen
Press the X button to continue. Now you should be at the DosBox main menu
Hold down the left arrow key on the d-pad and then press the X button. This will put the virtual keyboard in to numeric mode. Now press the square button twice to get in to the boot menu which will look like this
Now to load windows 95 you’re going to press the square button and then the triangle button. Your screen should then turn blue and a small message should appear at the top, just press the X button to go on. After a few seconds Windows 95 should start to load. You will probably be waiting for a couple minutes for this to load, after all your PSP is trying to emulate a X86 device, so patience is needed.
Yes even on a PSP Windows makes you run scandisk.
After another minute your PSP should boot in to Windows, you will see a screen asking you to set the time. Don’t bother setting the correct time because the system will not remember it. By the way your analog stick is used to control the mouse and the top left and right trigger buttons are used for your left and right mouse clicks.
You should now see your desktop, go head and play around for a bit.
You probably won’t stay in Windows for too long being everything will run sooo slow. Most of the programs I tried to open resulted in a system error. If you would like to see this in action before you try it yourself there are a bunch of videos on Youtube you can watch. Also none of the linked files were created by me, so don’t be mad if they melt your screen. 
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Have fun!
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