Shel Silverstein

Listen to the MUSN'TS, child
Listen to the DON'TS
Listen to the SHOULDN'TS
The IMPOSSIBLES, the WON'TS
Listen to the NEVER HAVES
Then listen close to me-
Anything can happen, child
ANYTHING can be.

Shel Silverstein is best known as an author of offbeat children's poetry. He also wrote picture books and song lyrics (most famously "A Boy Named Sue"). Fans of his mainstream work may be rather stunned to hear that many of his songs are very adult in tone, and that he personally was a real-life Chick Magnet who lived in the actual Playboy Mansion.

His books include:

A Light in the Attic (poetry collection)
Where the Sidewalk Ends (poetry collection)
The Giving Tree (picture book)
Uncle Shelby's ABZs (alphabet book consisting of Blatant Lies and intentionally terrible advice)
Wordless Dances (collection of adult-themed cartoons)
Falling Up (poetry collection)
Runny Babbit (poetry collection, published posthumously)
Every Thing On It (poetry collection, also posthumous, probably the last one)

Tropes appearing in his work:

Abusive Parents:
- In the poem "Every Lunchtime," the kid's mother packs a venomous snake in his lunch every day.
- In the poem "Quality Time", a father takes his son golfing... and uses him as a tee.
Affectionate Parody: The song "Sylvia's Mother" is an Affectionate Parody of heartbroken teen love songs.
AI Is a Crapshoot: The poem "My Robot."
All Girls Like Ponies: The poem "Little Abigail and the Beautiful Pony". Let's just say it doesn't end well.
An Aesop: Quite often, though sometimes sliding into Family-Unfriendly Aesop. For example, in "The Great Smoke Off":

And underneath his fingers
There's a little golden scroll
That says, "Beware of being the roller
When there's nothing left to roll."

- And another, from "Perfect High":

"Well, that is that," says Baba Fats, sitting back down on his stone,

Facing another thousand years of talking to God alone.

"It seems, Lord", says Fats, "it's always the same, old men or bright-eyed youth,

It's always easier to sell them some shit than it is to give them the truth."

Apocalypse How: Justified in "Hungry Mungry", when Mungry starts out by eating his parents, and then proceeds to go all the way up to Class X-4 by eating up the United States, the world, the universe, and finally himself!
Apocalyptic Log: The poem "Boa Constrictor".
Author Existence Failure: Runny Babbit
Auto Cannibalism: "Hungry Mungry" ends with Hungry Mungry eating himself, after having already eaten the rest of the universe.
Bald of Awesome
Batman Gambit: In "A Boy Named Sue," the reason the father named him that is because he knew he wouldn't always be there for his son, so he named him Sue so he would grow up hardened and strong from being bullied and picked on.
Best Served Cold: The song "A Boy Named Sue".
Bound and Gagged: The poem "Kidnapped", complete with illustration of excessively tied and chained girl.
Companion Cube: The poem "Snowball," in which the narrator makes himself a pet snowball. It melts.
Covers Always Lie: Where the Sidewalk Ends has a cover drawing with two children peering over the edge of the earth - however, this is not "Where the Sidewalk Ends" - this illustration is from a different poem in the book called "Edge of the World". The actual poem about "Where the Sidewalk Ends" is about the grassy spot between the sidewalk and the street, and has no illustration in the book.
The Complainer Is Always Wrong: The poem "Complainin' Jack".
Daddy Had a Good Reason For Abandoning You: "A Boy Named Sue".
Dancing Pants: The Trope Namer is a poem in Where The Sidewalk Ends.
Dead Baby Comedy: See Eats Babies below.
Death by Gluttony: "Pie Problem"
Death by Irony:
- The poem "Fear (Barnabas Browning)", where the titular character is so afraid of drowning that he refuses to leave his room. He dies by literally crying an ocean and drowning in his own tears.
- The poem "Ladies First", in which Pamela Purse is always using the title excuse for her selfishness. When the group gets caught by cannibals and are about to be eaten by the king, she still goes, "Ladies first!"
Dual-Meaning Chorus: The song "I Got Stoned And I Missed It".
Duck: The poem "Web-Foot Woe".
Embarrassing First Name: "A Boy Named Sue".
Eats Babies: "Someone Ate The Baby". It was the narrator.
Empty Swimming Pool Dive: The punchline of "The Dive".
Flat World: The poem "The Edge of the World." The illustration for this poem is also on the cover to the collection Where the Sidewalk Ends.
Gag Penis: The song "Stacy Brown's Got Two".
A Good Name for a Rock Band: It is one; there's a band called Silverstein.
Hair Wings: He has a poem about a boy with ridiculously long hair who was mercilessly teased about it until his weeping caused it to flap like wings, carrying him into the air.
Headphones Equal Isolation: The poem "Headphone Harold".
Hurricane of Excuses: The poem "Sick".
I Will Wait for You: The song "In the Hills of Shiloh".
Killer Rabbit: "Sybil The Magician's Last Show". The eponymous magician can't be bothered to buy food for her rabbit, so when she goes to pull him out of her hat one night, he pulls her into the hat and eats her.
Long List: The poem "No".
Mermaid Problem: The song "The Mermaid".
Multiple Head Case: The poem "Us".
Naked People Are Funny: A number of his poems deal with states of undress, as well as the fact that some illustrations in his works feature images of characters being naked for apparently no reason.
Neat Freak: The poem "Clean Gene".
No Ending: A number of his poems end with the story unresolved, such as "Sarah Cynthia Sylvia Stout". This trope was the whole point of his poem "Suspense", where a Damsel in Distress is Chained to a Railway by one villain, while The Hero is being held prisoner by another. And then a fifth character shows up, and it's unclear whether he's a hero or villain. "And a crash and a cry, and I'm sorry but I have forgotten the rest of the story" is the final line.
Not a Mask: The poem "Best Mask?" is a rare example where the maskless person is the narrator.
Now I Lay Me Down to Sleep: Parodied in "Prayer of the Selfish Child".

Now I lay me down to sleep;
I pray the Lord my soul to keep.
If I should die before I wake,
I pray the Lord my toys to break,
So none of the other kids can use 'em...
Amen.

Phony Psychic: In the poem "Crystal Ball", the psychic accurately predicts everything her customer ate for lunch, then admits that she only figured it out by looking at her dress.
The Pig Pen: The poem "The Dirtiest Man In The World".
Playground Song: "Boa Constrictor" has turned into one.
Playing Sick: "Sick".
Posthumous Narration: The poem "True Story", played for laughs.
Prayer of Malice: "Prayer of the Selfish Child".
Reptiles Are Abhorrent: "Boa Constrictor".
Sanity Slippage: The song "A Front Row Seat to Hear Ole Johnny Sing", where he goes to increasingly absurd lengths to get Johnny Cash tickets... and his delivery gets increasingly less sane throughout the song, to the point that he's practically screaming at the end.
Scare'Em Straight: "Little Abigail and the Beautiful Pony" ends with Abigail dead since she didn't get the beautiful pony. A note at the end suggests children should read it to their parents if they refuse to buy something for them.
Single-Stanza Song: The song "26 Second Song".
Spoonerism: The entire point of Runny Babbit is what would happen if onset metathesis was grammaticalized.
Tempting Fate: In the poem "Cookwitch Sandwich," the kid tells the witch cook to make him a sandwich. Insert predictable punchline here.
Trademark Favorite Food: Peanut butter sandwiches for the king in "Peanut Butter Sandwich", almost to the point of addiction.
Trash of the Titans: The poem "Sarah Cynthia Sylvia Stout".
Turtle Island: "Hungry Kid Island"
Was It Really Worth It?: Played for laughs in the poem "Big Eating Contest".
When I Was Your Age: Amply demonstrated in the poem "When I Was Your Age".
Who's on First?: The poem "The Meehoo with an Exactlywatt".
A Worldwide Punomenon: In the poem "The Monkey," several words are replaced with numbers. Many replacements are painfully forced.