On the wiki, they say the Wheels of Steel quest is a reference to the 18 Wheels of Steel game.
It's really based off of the song, Wheels of Steel. Pretty obvious, seeing as everything else is a song reference. The wiki REALLY needs work. If I wasn't limited to getting online with my phone right now, I'd redo the whole damn site myself.
This is my super "secret" board. Keep out. http://www.gamefaqs.com/boards/gentopic.php?board=565572