Let's not look at grammar as a cold, harsh mistress. She can also be a fun, kooky aunt. Here are some tricks you can do to make crazy sounding sentences that are still grammatical.
1. One morning I shot an elephant in my pajamas. How he got into my pajamas I'll never know.
Take advantage of the fact that the same sentence can have two different structures. This famous joke from Groucho Marx assumes that most people expect the structure of the first part to be
One morning [I shot an elephant] [in my pajamas].
But another possible, and perfectly grammatical, reading is
One morning [I shot] [an elephant in my pajamas].
2. The horse raced past the barn fell.
Make a garden path sentence. In this one, we think we've reached the main verb when we get to "raced," but instead we are still inside a reduced relative clause. Reduced relative clauses let us say, "the speech given this morning" instead of "the speech that was given this morning" or, in this case "the horse raced past the barn" instead of "the horse that was raced past the barn."
3. The complex houses married and single soldiers and their families.
Another garden path sentence, this one depends on the fact that "complex," "houses," and "married" can serve as different parts of speech. Here, "complex" is a noun (a housing complex) instead of an adjective, "houses" is a verb instead of a noun, and "married" is an adjective instead of the past tense of a verb.
4. The rat the cat the dog chased killed ate the malt.
Make a sentence with multiple center embeddings. We usually have no problem putting one clause inside another in English. We can take "the rat ate the malt" and stick in more information to make "the rat the cat killed ate the malt." But the more clauses we add in, the harder it gets to understand the sentence. In this case, the rat ate the malt. After that it was killed by a cat. That cat had been chased by a dog. The grammar of the sentence is fine. The style, not so good.
5. Anyone who feels that if so many more students whom we haven’t actually admitted are sitting in on the course than ones we have that the room had to be changed, then probably auditors will have to be excluded, is likely to agree that the curriculum needs revision.
Another crazy center-embedded sentence. Can you figure it out? Start with "anyone who feels X is likely to agree." Then go to "anyone who feels if X then Y is likely to agree." Then fill out the X and Y. You might need a pencil and paper.
6. Buffalo buffalo Buffalo buffalo buffalo buffalo Buffalo buffalo.
Buffalo! It's a noun! It's a city! It's a verb (meaning "to intimidate")! We've discussed the notorious buffalo sentence before, but it never stops being fun. It plays on reduced relative clauses, different part-of-speech readings of the same word, and center embedding, all in the same sentence. Stare at it until you get the following meaning: "Bison from Buffalo, New York, who are intimidated by other bison in their community, also happen to intimidate other bison in their community."
7. This exceeding trifling witling, considering ranting criticizing concerning adopting fitting wording being exhibiting transcending learning, was displaying, notwithstanding ridiculing, surpassing boasting swelling reasoning, respecting correcting erring writing, and touching detecting deceiving arguing during debating.
This sentence takes advantage of the versatile English –ing. The author of a 19th century grammar guide lamented the fact that one could "run to great excess" in the use of –ing participles "without violating any rule of our common grammars," and constructed this sentence to prove it. It doesn't seem so complicated once you realize it means,
"This very superficial grammatist, supposing empty criticism about the adoption of proper phraseology to be a show of extraordinary erudition, was displaying, in spite of ridicule, a very boastful turgid argument concerning the correction of false syntax, and about the detection of false logic in debate."
Not only is this a great example of the wonderful crazy things you can do within the bounds of proper English, it's the perfect response to pull out the next time someone tries to criticize your grammar.