When considering the question " How much wood would a woodchuck chuck if a woodchuck could chuck wood?" as a child, or the last time you considered it, if ever, did you imagine the woodchuck actually doing something that falls within the definition of the word “chuck”(toss, disregard, etc.)? Or did you imagine that woodchuck gnawing on wood or something else that you might suppose a woodchuck was prone to do? Until tonight while I was ironing, I had never imagined that woodchuck throwing wood around.
I always imagined the woodchuck chipping off chunks of wood with his two front teeth, which, in my head, were probably much bigger than actual woodchuck teeth.
I always imagined the woodchuck sort of ripping & digging its way through wood and tossing the bits behind it.
Interestingly, someone came up with an answer, mentioned in the response to an old Straight Dope column:
Not being from somewhere with woodchucks, I had no idea what behaviour they might actually, more realistically indulge in. So I just straight out imagined a woodchuck chucking wood.
What he said.
Chew a bit of wood…chuck it.
Chew another bit of wood…chuck it too.
Why do woodchucks chew wood if they’re only going to chuck it at the end of the gnawing? 
Me likewise – just pictured the beast vigorously throwing large amounts of logs / branches / planks around, with gleeful abandon.
Topic-drifting slightly: is it true that the word “woodchuck” is a corruption of wuchak– the creature’s name in a Native American language? I came across this statement, via a source reckoned often suspect as regards accuracy.
Well, the answer quite obviously is that:
A woodchuck would chuck all the wood a woodchuck could chuck if a woodchuck could chuck wood.
Fetched up from the past by this thread – a matching bit of nonsense in my family, growing up: “How much oil would a gumboil boil, if a gumboil could boil oil?”
<ZOT!>
You can’t JUST ask how much wood he can chuck.
You have specify two of three factors: an amount chucked, a time frame in which to chuck it, and a method or quality level of the chucking.
Give us two and we’ll give you the third.
I always pictured the little critter chucking wood into a stream to form a damn.
I think you should also consider the amount of wood available to be chucked. Some addendum to Parkinson’s Law might apply to this situation.
That’s a beaver, not a woodchuck.
How much ground round would a ground hog hog if a ground hog were ground round?
I always thought Geico got it wrong:
I thought it was a form of gnawing. “Chuck” as a verb to throw away wasn’t common in my experience when I was young enough to wonder about those chuckers. Why would they throw it away? It’s good wood!
Q: If a centipede a pint, how much would a precipice?
A: A sheer drop.
How much ground round would a hound dog hog if a ground hog was ground round? --Walt Kelly
It was common enough in my neck of the woods (though woodchucks weren’t). The alternative meaning was essentially “to tighten in the jaws of a tool, usually a drill”. Given the latter meaning, the answer would be “one fairly small stick”, so it actually provides a more definitive response.
In my elementary school, the second part of that saying went: “A woodchuck would chuck all the wood if a woodchuck could chuck wood.”
I’m not convinced that a woodchuck would chuck any wood at all, even if he or she could. Woodchucks are seldom bothered by unchucked wood.