10 Classic Kids Books That Defined Millennials' Childhoods (2024)

A handful of standalone books and book series defined the childhoods of millennials due to their timely themes or popularity in the 1980s and 1990s. These classic kids' books from the 90s are still worth reading for their literary merit as well as nostalgia for the time. Some books were defining cultural moments for young millennials because of their reception when they first came out. Others were released earlier, but are still important to this generation as they are still required reading material and demonstrate some resonant themes.

Some of these books are assigned school reading books people would pick up today, due to genuinely enjoying the book they read for class. These books reflect themes that were important to the millennial generation: idealized independence, undertones of fun horror, and a dose of existential dread. Some of these books completely transformed their genres in their time, and the legacy of millennial literature is still seen today.

10 Scary Stories To Tell In The Dark

By Alvin Schwartz

Scary Stories to Tell in the Dark is the perfect example of the morbid fascination with horror aimed at kids in the 1990s, the decade that saw the release of The Nightmare Before Christmas. This title might be counted alongside transitional movies and TV shows to introduce kids to horror. The illustrations drawn by Stephen Gammell are a huge part of the appeal of Scary Stories to Tell in the Dark, providing kids with thrills and scares through a medium arguably utilized specifically for them.

Scary Stories to Tell in the Dark was also a cultural phenomenon in the 1990s because of how much it was challenged by parents, demanding it be banned from school libraries. Although the first volume was released in 1981, the following era is when this really picked up; the American Library Association named it the most contested book of the decade. However, this would have only made Scary Stories to Tell in the Dark a more classic example of 90s rebellion.

9 Charlotte's Web

By E. B. White

Although Charlotte's Web was already a few decades old by the time millennials were reading, it was still a formative classic for this generation, perhaps being counted among the books that traumatized millennials. The premise of Charlotte's Web is simple but provokes philosophical thinking, showcasing the perspective of barnyard animals who are aware of their value to humans. It also explores themes of the natural circle of life and death, concluding with the title character's death and three of her daughters taking her place in the barn.

Charlotte's Web is still a staple of introducing children to literature, but it was more popular in the 1980s and 1990s. Maybe the subpar movie adaptations in the 2000s ruined the effect. However, with millennials coming of age at the beginning of a new millennium (hence their name), the generation was inherently about one thing ending and another beginning. Charlotte's Web reflects this same theme through the lens of personified animals trying to save one of their friends while accepting the loss of another.

8 The Boxcar Children

By Gertrude Chandler Warner

The Boxcar Children first hit bookstores in 1924, was reissued in 1942, but only picked up as a series from the 1950s onward. The first 19 books were written by first grade teacher Gertrude Chandler Warner, but the series was carried on by other authors. It still publishes new titles today, now totaling more than 160 books. The series follows four orphaned siblings who create a home for themselves in an abandoned boxcar, solving many mysteries along the way. They are later adopted by their wealthy grandfather, who has the boxcar moved to his backyard.

The Boxcar Children books were popular throughout the decades, only tapering off in the 2000s with the rise of other children's series, although still selling enough copies to warrant its continuation. Stories about independent children going off and having their own adventures will always appeal to younger readers, but this would be especially true of millennials, arguably the first generation to have helicopter parents. The Boxcar Children demonstrates some of the most popular tropes of children's literature, making it an easy sell.

7 Roald Dahl's Books

By Roald Dahl

Roald Dahl's career also predates millennials, but his corpus was standard reading material for children in the 1990s and 2000s. While Charlie and the Chocolate Factory, Fantastic Mr. Fox, and James and the Giant Peach are from earlier in his career, some of his most famous titles were published within millennials' birth years. This includes George's Marvellous Medicine, The Witches, The BFG, and Matilda, now also a Broadway musical phenomenon. His books are mildly disturbing yet wonderfully imaginative, speaking to young readers across the years.

The movement created by Dahl in literature might have gone on much longer, but the author passed away in 1990. His depictions of cruel adults and freethinking children capable of outsmarting them are also widely appealing, encouraging readers to think for themselves. It is mainly due to his career ending and no new material coming out that the children of the 1980s and 1990s are more defined by Dahl — but his books are still popular today.

6 The Secret History

By Donna Tartt

The Secret History was more suited to millennial teenagers than children, but is still a defining moment of 1990s literature. The book almost single-handedly kickstarted the dark academia genre, although its characteristic supernatural elements would come later. While The Secret History was mostly praised by critics with some negative reviews when it was first released, it was immensely popular among readers and would have been the BookTok phenomenon in its time.

The Secret History also plays into some other popular genres of the 1990s, namely grim mysteries and classical-gothic aesthetics. High school students would have turned to this for something entertaining as well as intellectual. With other dark academia standalones coming out in the 2000s and bigger fantasy series taking over at the end of the 1990s, the bulk of the decade belonged to The Secret History alone.

5 Goosebumps

By R. L. Stine

The only series that has a bigger presence in the horror genre for millennials than Scary Stories to Tell in the Dark is R. L. Stine's famous Goosebumps series, also comprising many nightmarish standalone adventures. The full collection of Goosebumps properties is astounding, including the original series of 62 books, a spinoff series, a series of short story anthologies, and various adaptations and tie-ins. After a low-key reception to the first book, word gradually spread about Goosebumps and a massive phenomenon began to take shape.

Every millennial was fascinated by Goosebumps and kept returning to the novels for more terrifying tales. Iconic characters like Snappy the Dummy became famous in pop culture, while Goosebumps doubtlessly contributed to the proliferation of children's horror in 1990s. The combined movements of Goosebumps and Scary Stories to Tell in the Dark shaped a vibrant and terrifying subgenre within millennial youth culture.

4 Holes

By Louis Sachar

Coming out towards the end of the 1990s and therefore being enjoyed by younger millennials as children, Holes is a uniquely disturbing mystery and adventure book that is a staple of 2000s standalone literature. It follows a teenager who is falsely accused of a crime and sent to a juvenile detention camp where the boys spend all day every day digging holes. Although they don't know it yet, the cruel warden is after a treasure that is foundational to the mystery of the story.

Through the lens of children's literature, Holes is a well-crafted look at a corrupt justice system. The relationships among the boys, both in how they bully and defend each other, comprise an emotional an resonant story. Stanley and Zero slowly uncover a history of exploitation at Camp Green Lake which led to the circ*mstances they are in and reveals how they can escape it. Along the way, the reader gets to know some underrated, iconic characters brought to life by A-list actors in the movie adaptation.

3 The Baby-Sitters Club

By Ann M. Martin

The Baby-Sitters Club showcased self-sufficient and business-savvy endeavors for younger millennials to aspire to, while delving into various different experiences of childhood including divorce, blended families, moving, illness, and losing family members. An original group of four friends formed the BSC, a babysitting service for the residents of their fictional suburban town in Connecticut. The roster of babysitters changed over the years, allowing the series to explore new dynamics among the club, their families, and their clients.

Along the way, the members of the BSC have typical coming-of-age experiences like first crushes and petty rivalries. In summary, The Baby-Sitters Club is a depiction of a normal teenage suburban experience that crams in a lot of varieties of this upbringing, released right in the middle of millennials' birth years. The original author Ann M. Martin wrote the first 35 books consecutively but is said to have written more, while several ghostwriters were brought in to carry on the series.

2 Harry Potter

By J. K. Rowling

Harry Potter is the biggest cultural event of a generation, which also came out at the end of the 1990s, when millennials were coming of age. As a coming-of-age story itself, Harry Potter was perfectly timed for a generation also heading into the scary world of adulthood. Interestingly, Harry Potter actually takes place during the 1990s rather than mostly after it, with its starting point several years before its release date. Because the Wizarding World is somewhat divorced from Muggle culture, Harry and his friends are both typical 90s kids but have no sense of what defined the decade.

On the other hand, the fact that Harry Potter was just the most popular series in the world at the time made it a defining moment for millennials, rather than any thematic elements that specifically spoke to them. Things were slower for the first few books, which were the most popular in the UK. However, Harry Potter began to expand into something completely unprecedented in the early 2000s. The whimsical yet grim aesthetics of the Wizarding World overtook a generation and has remained popular.

1 Where The Sidewalk Ends

By Shel Silverstein

On the other hand, the works of Shel Silverstein are thematically in tune with Y2K, offering a distorted version of Dahl's literary repertoire. "Where the Sidewalk Ends" is a vivid and enigmatic poem that promises a scary but exciting adventure into the unknown, with an inevitable end coming soon. Meanwhile, many of the poems in Where the Sidewalk Ends also exhibit themes of questioning authority, something that was important to youth culture from the time it was released up until millennials came of age.

Its rebellious attitude is also one of the reasons it was a highly contested book, as well as the satire being used to address mature subject matter (via Banned Books Awareness). However, Where the Sidewalk Ends also saw re-releases for its 25th and 30th anniversaries, the timing of which demonstrates its impact on millennials. It's fanciful yet serious nature is exactly what would have spoken to millennial children, who sought out similar books that slotted into current cultural trends.

Source: American Library Association, Banned Books Awareness