Ask and it shall be given:

This will need some editing, I'm sure (I think I randomly switch tenses at a couple of points), but I do so love the Littlest Hobo. Here we get an idea of what started him on his life of adventure, and where he gets his giant hat! Enjoy, I guess.

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On this fine, sunny day we find the Littlest Hobo was walking down a dusty road, as we so often seem to do. It's a wonderful day for walking, the sky is clear, the air is warm, but not too much, and with just the perfect breeze to keep you cool as you go. Despite this, the Littlest Hobo, having been walking for quite some time, found himself sweating to quite some degree. It had, in fact, been a number of days since he'd given his feet rest, and what little water was left in his dehydrated body was dripping in small beads directly into his already sore, stinging eyes.

There wasn't much he could do about this difficulty; being so small, it took all of the strength of his feeble arms to keep the giant stick (not so large to you or me, but simply gargantuan to our diminutive mutual friend) from which his rucksack hung firmly rooted to the cavity his shoulder had long since created for it. Beyond this, his extreme weariness cautioned him from merely blinking the fluid away, for he knew that upon closing his eyes, he was likely to fall asleep in his exhaustion, and we all know quite well by now what that means for poor L.H.

And yet through all of these difficulties, the Littlest Hobo manages to keep his spirits high. He has noticed quite some time ago that his awkward, hobbling pace just happens to provide the exact rhythm to hum along one of his favorite songs. It is a melody his sweet mother had sung for him in the days before that ever so finely clad pimp showed up at their door to take her away. The memory was as clear as always: He first recalls the question he had asked this dashingly tailored whoremonger, "Kind sir, why are you making an orphan of me?"

Upon discovering that the inquiry had come from somewhere near the vicinity of his knees, the pimp responded in plain "Quite simply, boy, your father has wracked up quite the debt in his infidelity; and your sweet mum is the only collateral he could offer." As he peered downwards to say this, his beautifully plumaged hat tipped from his head, wafting onto the meager dome of our friend, the soon-to-be vagabond. Overwhelmed by the apparent generosity of this spectacular gift, the Littlest Hobo (as he is now known, though he of course wasn't then) started to tear up. Misunderstanding the significance of what was welling up in our picayune playmate's eyes, the princely purveyor of prostitutes exited with great expediency, not even waiting to hear the strained words of heart-felt thanks the followed after him.

The vultures, eternally circling, cut off their accompaniment, bringing the Littlest Hobo back to the present, where the fluid building in his eyes was of another, much more agitating sort. After checking to make sure they weren't preparing for another swoop, the Littlest Hobo allows himself a wheezing chuckle. "How ironic it is that a trader of tramps should make a tramp of a completely different sort of me!" He rejoices in the bittersweetness of it. What a fond thing it is when you only need to remember one day to recall receiving both your proudest possession and the commissioning of your life's work!

With this small bit of refreshment, the Littlest Hobo picks up his pace once more and continues his journey, anxiously waiting to see what sorts of adventures lay down the road he's been thrown upon.