Sherri Ryan of Sonic 102.9 does a countdown show every Tuesday night where she picks a random thing and plays the top ten songs in that category. Sadly, I am either busy coalmining or, uh, watching House at that time so I have yet to actually hear her show. Luckily she posts her list every week on her blog. Remember my top seven six songs about vampires? Compiled when I was trapped in the Crypt.
The reason I bring it up is I have been trying to come up with a top ten list about coal mines, or heavy equipment, but pretty much stalled out at "Coal Mine" by Armchair Cynics. And that song isn't even about coal mining! But just tonight someone told me about this really cool song and video out there that fits the bill as far as being about machinery, and has the added bonus of having that wistful/reminiscent/childhood whimsy vibe I dig so much. Check it out: JCB Song, by Nizlobi.
Also, you should really check out House. He makes me laugh, with all his childlike whimsy!