Randomly play audio files on windows media player with Arduino

What threads have you read?

Post links please.

First off.. you would probably need to use an Arduino that is capable of acting as a HID (human input device)..
*(like a mouse or keyboard..etc)

this will allow you step 1 of having your external device/circuit be able to communicate with your PC

The next bit/step is a bit tougher....

How do you start, control and set a file for WMP to use?

Is there an API? Some sort of shortcut you can do this on your PC (without an Arduino?)

Alternately.. a regular Arduino (UNO) sending data via serial port to the PC could also work..

however. you still need an interpreter app and a way to send these actions to the WM player..