For this achievement you must listening an online radio station at least 2 hours in-game.
To insert a radio station you must edit this file on you computer:
c:\users\[your_user_name]\documents\trucks & trailers\live_streams.sii
I found an online radio station on the internet and inserted this row to the file:
stream_data[]: "
http://5243.live.streamtheworld.com/M80RADIO_SC|M80 Radio"
After pressing the button for the radio then you need select the station what inserted before and press the Play button on the screen.
Must selecting the radio again after returning to the menu, but can listening continously if playing the next job or restarting it if failed. Or simply start the radio and wait 2 hours in that place. :-)
My achievement popup only after finishing the current job, not in the middle of play.