Unfortunately, running Road Rash on a modern PC isn't as straightforward as you would like it to be. There is no digital re-release and sticking the CD-ROM into the drive will throw up all sorts of errors if you are running anything above Windows 95.
Don't fear, I'm here to make this nice and simple for you. I'm no genius, and all that you read below is as result of me collating advice and tools I have found elsewhere on the internet.
STEP 1 - Put the disc in your PC
If you don't already have a copy of the game, you should be able to grab a copy from eBay for around a tenner. Here's one I bought earlier.
If you have gone digital only, you can emulate your ISO or BIN/CUE file using DAEMON Tools Lite, which is free and fools your PC into thinking you have a physical disc in a CD-ROM reader.
Otherwise, simply shove your CD-ROM into the disc tray and shut it! Ignore any prompts from Windows to open the disc, or autorun the installer. You don't want to do that.
STEP 2 - Launch a special installer
Yeah, I said special! I tried several methods online to "hack" the game to work, from replacing the game .exe to changing command lines. This is by far the most successful and simple solution I have found online.
Thanks to Mr.Blade from the German retro gaming community REPLAYING, you can download a simple launcher which will detect the game in your CD drive and do the rest for you. Click here to download the Road Rash Windows 7/8 launcher. Choose your desired installation location and install! Note that when you want to uninstall the game, you don't need to go to the Windows uninstaller, you simply delete the game folder.
REPLAYING is dedicated to resurrecting games such as this one, so take a look around!
STEP 3 - Configure a controller
As Road Rash (Windows 95) is super old, it doesn't understand modern devices such as the Xbox 360 Controller for Windows. My advice will work for any controller that uses XInput, which is what most drivers for PlayStation DualShocks on Windows use.
What we need is some software that translates gamepad button presses into keyboard inputs. My preference is Xpadder - which although isn't free, allows you to create very detailed profiles, which can be useful for a game like Road Rash.
You see, Road Rash has two inputs for controlling your bike - Steer and Lean. With Xpadder, you can configure it so that moving the left stick a little bit steers the bike. Pushing the stick a little further activate the Lean - giving the impression of analogue controls. It's awesome! You can download my pre-made profile here.
Alternatively, you can try configuring your own controls for free, using Joy2Key, which is also an excellent solution for playing older games on your modern controller. If you have a DualShock 4 handy, Input Mapper is a very solid tool which not only lets you use the controller with Windows (via USB or Bluetooth), but let's you map your gamepad to keyboard inputs, with advanced controls much like Xpadder.
Remember to leave your software running before you...
STEP 4a - Launch the game!
Now, Mr.Blade's installer tells you to run Start.exe from inside the game folder, but this doesn't work for me. I simply launch ROADRASH.exe and it works fine, without changing any Windows compatibility settings or anything!
STEP 4b - Something's wrong!
Some people seem to have graphics issues with Windows 7 64-bit. REPLAYING are back to the rescue with this nifty patch, which will hopefully sort you out.
I'd love to hear if you found this guide useful at all. Please feel free to comment below if you have any questions or problems and I can try to help you out! Trust me, it's worth it to play this amazing version of the game.