- Write What You Know: Many of dePaola's books are autobiographical in naturenote , and his family features prominently in such stories.
- The Baby Sister chronicles the birth of Tomie's little sister, Maureen (who would remain his best friend until the day he died).
- Tom highlights the Intergenerational Friendship he had with his maternal grandfather (and namesake), Tom Downey.
- Now One Foot, Now the Other delves deeper into their relationship, and details how the former helped the latter to recover from a stroke.
- The Art Lesson explores how dePaola's passion for art began.
- Oliver Button is a Sissy showcases dePaola's childhood love for performing, and the bullying that he suffered from some of his male peers.
- His love of performing is also explored in Stagestruck, in which he recalled his experience being cast in his school's production of The Tale of Peter Rabbit.
- Nana Upstairs & Nana Downstairs is about his relationship with his maternal grandmother, Alice Downey ("Nana Downstairs"), and great-grandmother, Honorah Mock ("Nana Upstairs").
- My Mother is So Smart is a love letter to Tomie's mom, Flossie.
- The 26 Fairmount Avenue series — Tomie's first venture into writing chapter books — explores events in his childhood that he hadn't written about before, along with those explored in his storybooks.
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