Over at Mental Floss, I found some of the oddest sentences that are perfectly grammatical and yet which don’t compile  properly.
One of the most famous is,
“Buffalo buffalo Buffalo buffalo buffalo buffalo Buffalo buffalo.”
A visual explanation of this monstrosity is the most effective:
You can also visit Wikipedia for a detailed linguistic deconstruction; like Columbus’ egg (an appropriate simile for today) , it’s easy when you see what they’re doing.
However, only slightly less well known is this one:
Never go in against a Sicilian sorry, I meant
“The rat the cat the dog worried killed ate the malt.”
This is an example of nested relative clauses. The structure is easy to follow when only few are used:
The rat ate the malt. The cat killed the rat. These become, “The rat (that) the cat killed ate the malt.”
Add in “The dog worried the cat” and you get “The rat (that) the cat (that) the dog worried killed ate the malt.” Since the subordinating conjunction “that” is optional in such clauses, the resulting sentence begins to become incomprehensible as the nestings are more and more difficult to follow.
The human mind is a wondrous machine, capable of prodigious feats of memory, calculation, and creativity, but it can only perceive so much at a single glance. In the case of determining how many items are within a field of vision, this skill is called subitizing, and the current human limit seems to be between five and seven.
Quick, how many dots?
Three. No challenge, right? Now try this one. Quick, no counting!
The answer is “24,” but you didn’t know that without counting, unless you happen to be one of those few people, either autistic or supergenius, who has somehow bypassed the normal human ability.
But let me show you the same number like this:
And while you can’t subitize the dots, you can immediately calculate how many there are based on your encyclopedic knowledge of the universe and a bit of simple math.
In the same way, the human mind is able to understand and generate language, but there are limits to how much complexity can be comprehended, even if all grammatical rules are followed. Thus taking our example to its logical conclusion, “The House that Jack Built” becomes:
This is the malt the rat the cat the dog the cow3 the maiden4 the man5 the priest6 the cock7 the farmer8 kept waked married kissed milked tossed worried killed ate, that lay in the house that Jack built.
It’s interesting from a scholarly standpoint, but nowhere near as fun to recite while bouncing your grandchild on your knee.
Remember, time flies like an arrow, and fruit flies like a banana.
The Old Wolf has spoken.
 This is computational linguist slang for “I don’t get it.”
 I am 1/2 Italian by descent. As such, Columbus Day has long been a great celebration, especially in New York where I grew up. Sadly, in much the same way as we now know that brontosaurus is now an apatosaur, and that Pluto is no longer a planet but a Trans-Neptunian Object, we now know that Columbus is not the national hero he has been made out to be; October 14th would better be renamed “Genocide Day.” Yes, he played a significant rôle in the development of this nation, but the human toll that was left behind in his wake is staggering. A couple of things you might be interested in reading are at The Thunder Mountain Monument, The Oatmeal, and Lies My Teacher Told Me.
 with the crumpled horn
 all forlorn
 all tattered and torn
 all shaven and shorn
 that crowed in the morn
 sowing his corn