* 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.
* CrossesTheLineTwice: The poem "Screamin' Millie." She screams so loud that she literally explodes, and it's explored in gruesome detail.
* NightmareFuel: The picture of the skin-stealing coo-coo on page 147 of ''A Light in the Attic''.
** The narrator of ''Obedient'' is told to stand in the corner until told to leave. Then the school day ends, but nobody's told him to leave. But it's Friday, so he stays there for the weekend. Monday is the start of summer break, and in the fall they tear down the school. Forty years later, he's still obediently standing in what's left of the corner, waiting.
* 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.
** 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.]]
** Benjamin Bunnn from Wilmington, whose buttons don't come undone, so he can't bathe or take his clothes off.
* 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.