- Anvilicious: The series, especially the books, seem to suffer from this.
- Ensemble Dark Horse: The Camel With the Wrinkled Knees appeared in only one book, but was so popular among fans that he became a major character in the movie and TV series, even one of the Fleischer cartoons.
- Fair for Its Day: While Beloved Belindy has a minstrel-show design and is explicitly a mammy doll, she has a fairly positive portrayal and is spared the offensive Funetik Aksent given liberbally to Dinah.
- Harsher in Hindsight: Shortly after the success of the Raggedy Ann doll, Johnny Gruelle's daughter Marcella was vaccinated a second time by her school without her parents' permission. The needle was contaminated and Marcella died from the infection in her father's arms when she was 13. Every Raggedy Ann book has since been written in her memory, "Marcella: A Raggedy Ann Story" being the prime example.
- Heartwarming Moments: "The Enchanted Square" is about a blind little girl named Billie who is given a Raggedy Ann doll which comes to life and shows her how to "see" with her imagination.
- "There's some who see with the eyes in their head, and there's some who see with the eyes in their heart."
- One story has Marcella being given two beautiful dolls as gifts. The dolls are snobs who make snide comments about how poorly-made Raggedy Ann is, but when they have no beds for the night (Marcella puts all her dolls in their own beds but had no time to get ones ready for the newcomers), Raggedy Ann moves them to hers. The dolls are so moved by this that one of them kisses Raggedy Ann when they think she's sleeping.
- Tear Jerker:
I'm just a rag dolly,
- The song based on the character. "I'm just a little girl, I'm Raggedy Ann, falling apart at the seams." The YouTube video of a live performance hits even harder.
- The song "I'm Just A Rag Dolly," or more specifically the stage musical version, which is a much more grim take on the song than we got in the animated movie. The last verse gets particularly bleak:
Wanting for times to be glad.
A little rag dolly,
Starting to slide into sad.
Wish I could be jolly,
Carefree wherever I roam —
But I'm a rag dolly, weighed down inside,
And my heart says "I wanna go home."
- Values Dissonance: Marcella has a mammy named Dinah who shows up on the "Raggedy Ann and the Washing" chapter, which may be uncomfortable for present-day readers. She also had an explicitly stated mammy doll named Beloved Belindy, who, while positively portrayed, was still very racist and creepy looking.