* AwardSnub: Silverstein was a Grammy winner and posthumously inducted into the Nashville Songwriters' Hall of Fame, but never won an award for the children's books, cartoons and poetry he's best-known for.
* CoveredUp:
** "A Boy Named Sue" is more known for the Johnny Cash cover.
** "The Ballad of Lucy Jordan" is best known as a Marianne Faithfull song.
** "Cover of Rolling Stone" is best known as a Dr. Hook and The Medicine Show song.
* CrossesTheLineTwice: The poem "Screamin' Millie." She screams so loud that she literally explodes, and it's explored in gruesome detail.
* HilariousInHindsight: One of his poems explores the idea of [[{{Disney.Frozen}} a snowman who wants to live to see July.]]
** He did not invent this idea. There is a German WWII era cartoon, Der Schneemann, in which a snowman actually does get to experience July, only for a few minutes, after staying in the freezer through spring.
** Another features a character named "[[WesternAnimation/SpongeBobSquarePants Dirty Dan]]" as the protagonist.
* NightmareFuel: [[NightmareFuel/ShelSilverstein has its own page]].
* TearJerker: The entirety of his last posthumously published book, ''Everything On It''. A large portion of the poems - including the very first one in the book, "Years from Now" - are surprisingly melancholy and sorrowful.
* WhatAnIdiot:
** The poem "My Sneaky Cousin", where the titular cousin has the bright idea of [[spoiler: riding in a washing machine.]]
** In the poem "Stupid Pencil Maker," the narrator is having trouble using a pencil. It does not occur to him to turn it pointy-side down.
** In the poem "Obedient," the narrator is told to stand in the corner. The teacher forgets to tell him to turn around, so he stays there. [[spoiler:FOR FORTY YEARS.]]
* WhatDoYouMeanItsNotForKids: Uncle Shelby's ABZ Book, which constructs perfectly logical-sounding reasons why children should do things like throw eggs at the ceiling and ask their parents for a gigolo.
** Children sometimes find themselves blindly wandering into his more mature work, like "The Smoke-off".
** ''The Devil and Billy Markham'' is most definitely '''''NOT''''' kid-friendly.
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