9 High School Classics Worth Rereading Now That You’re Older

High school. It’s some of the best and most carefree times of your life. You’re told over and over to appreciate it while you can – before the responsibilities of life hit full force. And of course, we never listen.

9 High School Classics Worth Rereading Now That You’re Older

No high-schooler thinks that this is as good as it gets. I certainly didn’t. But here I am, years later holding down a steady 9-5, three kids, battling the many hardships of life wishing for those simpler times. My only escape? Books.

And recently, I’ve been going back to the old but gold kind of novels. The classics that we were forced to read as younger adults. I can’t tell you how much more I enjoyed them because I was choosing to do so.

I also think that once you’ve been exposed to the harsh realities of life a few years later, these books resonate and hit you so much harder.

So ditch those preconceived notions that the high school classics are boring. Look at them with fresh eyes and see them for their true beauty and potential.

The 9 Classic High School Reads Worth Revisiting

To Kill A Mockingbird – Harper Lee

To Kill a Mockingbird

While it may not hold as much weight to younger school children, this novel has sold more than 40 million copies worldwide, is a major motion picture, and has often been voted the best novel of the 20th century. 

In this gripping, heart-wrenching, and soul-destroying tale, you will take a journey through a coming-of-age novel based in the South during a time of unfathomable prejudice and discrimination.

A young girl narrates the story as she watches her father risk everything in terms of his law career as he defends a black man that has been unjustly accused of a heinous crime.


  • Thought-Provoking – There are so many deeper themes running throughout this book that will most likely have gone over the heads of younger students. The dark and difficult topics are so much more profound and moving when read as an adult.
  • Naive Narrator – The use of narrator is so incredibly and carefully selected and its importance is so much more telling when you reread this as an adult. Prejudice, unkindness, and discrimination are all learned behaviors, and seeing this story through an innocent and naive mind only emphasizes this.


  • Difficult Jargon – There really aren’t many bad things to say about this classic. The only criticism I really have is that the jargon used throughout the book can be a little difficult to understand. It is quite wordy and is definitely not a light and quick read. It may require some perseverance, to begin with.

The Catcher In The Rye – J.D. Salinger

The Catcher in the Rye

The Catcher In The Rye is seen as one of the Great books of all time, which might come as a surprise to many since the premise of the story seems somewhat simplistic on the surface.

Holden Caulfield is a teenager who has recently been expelled from school for failing his classes.

Over the course of just a mere few days, we learn more about this anti-hero who seems simultaneously too simple and complex for us to make any real comment about him or his story.

During your reread, you’ll notice so much more about the influencing factors that create this protagonist/narrator and you’ll come to realize that he is simply a product of a specific time period and mindset.


  • Complex & Developed Character – During high school, I really only saw Holden Caulfield as a grouch and a pretty depressing character. But during my reread it became evident there was so much more to it than just this. Holden is an incredibly complex character that undergoes so much development throughout the novel.
  • Deeper Themes – Again, teenage me saw this as a relatively boring story were not much happened. Where were all the action and supernatural beings I was used to in my YA novels? Well, upon my rereading I realized that there was so much more to it. The alienation as a form of self-protection, the painfulness of growing older and losing your innocence, the phoniness that is prevalent in the adult world, religion, and keeping up appearances and performances. So much more lurks beneath that simple surface.


  • Vulgar Language – There is quite a fair bit of vulgar language and inappropriate circumstances throughout the novel. In fact, so much so that it has since been banned from many schools and libraries.

The Great Gatsby – F. Scott Fitzgerald

The Great Gatsby: The Original 1925 Edition (F. Scott Fitzgerald Classics)

Did you know that when The Great Gatsby was published it actually didn’t do that great in terms of sales? Now, it’s a bestseller classic and a household name.

And this might actually mimic your experience so far with the book – it wasn’t that great during high school but you’ll adore it now. The story is set during the roaring twenties when parties were rife…as was the drama.

The story is narrated by Nick Carraway a comparatively poor (but still somewhat affluent) individual that interacts with the enthralling millionaire Jay Gatsby who is infatuated with the stunning, and taken, Daisy Buchanan.


  • Important Themes – The Great Gatsby emphasizes that the American Dream is not real or achievable. Though this is something I learned in high school, it never really resonated with the same impact back then. Rereading this book after working to achieve this perfect ideal is so much more provoking and poignant.
  • Memorable Characters – The characters that Fitzgerald creates are so distinctive and each has their own representation and symbolism that is so much evident as an adult as opposed to a child.


  • Limited Emotions & Likeable Characters – Perhaps not quite the con it seems since many of the characters are intentionally emotionless and unlikable, but I do feel as if you are left without any real character to root for in this novel. Although, as I have mentioned, these characters are supposed to represent all that is wrong with the rich and wealthy and so it is unsurprising that we dislike so many of the characters that we meet.

One Flew Over The Cuckoo’s Nest – Ken Kesey

One Flew Over the Cuckoo's Nest

This is probably one of the few high school reads that I genuinely adored while I was still a teenager, but during my rereading of the novel, it became evident that even then most of the deeper meaning and themes had gone straight over my head.

In this classic tale, we meet Randle Patrick McMurphy, a boisterous, brawling, and fun-loving rebel who convinces the jury to send him to a mental hospital over a prison sentence.

But Randle soon learns that this might not be the easy option he had assumed it would be. This doesn’t stop McMurphy, however, from causing all kinds of trouble during his stay.

The life-affirming male tries to rally the other patients to stand up to the cold-hearted dictatorship run by Nurse Ratched. Throughout the story, he encourages gambling, the smuggling of alcohol, and so much more.

And what began as a rivalry soon expedites into a full-blown war between patient and nurse.

However, Nurse Ratched has the power of authority behind her and soon uses her ultimate weapon against McMurphy for an unbelievable climax to this shocking story.


  • Symbolism & Themes – There is an abundance of symbolism throughout this story, especially in the characters themselves. And this is so much more evident when you reread it as an adult. McMurphy represents sexuality, freedom, and self-determination while Nurse Rached clearly represents the oppression, dehumanization, and emasculation of modern society.
  • Poignant Message – While it may not be as obvious during your younger years, from an adult perspective there is such an important message in terms of mental health in this book. And as you get older and experience the struggles of mental health this only becomes more poignant. From McMurphy’s casual assumption that the mental institution will be easy sailing to Nurse Ratched’s treatment of her patience, it is evident that Kesey is highlighting the need for more kindness surrounding mental illness and understanding that treatment is not a one-size-fits-all.


  • Some View The Novel As Sexist – There has been some discussion about the fact that the novel promotes sexism and misogyny through various tools such as derogatory language towards women.

Fahrenheit 451 – Ray Bradbury

Fahrenheit 451

Set in a bleak, dystopian future, this classic novel only seems to become more relevant as the years pass by. Regardless of whether you enjoyed this novel or not during your youth, I can promise that it will only resonate so much more fiercely with you now.

Guy Montag works as a fireman. But not the kind that puts out fires, the kind that starts them. That is when homes are found to contain the most illegal commodity around – a book.

Books are banned and anyone found to possess them can expect them to be destroyed – along with the home they are hidden within.

Never questioning the destruction he leaves behind, Montag returns to his home and wife who spends her days watching shows on a television that takes up the entirety of the wall.

But when an eccentric woman by the name of Clarisse moves in next door, she reveals secrets of a past where people didn’t live in fear and a present where the world could be filled with stories that come to life in the form of books.

This leaves this fireman questioning everything he has ever known.


  • Key Themes That Are Still Relevant – This novel tackles important themes such as how censorship is a tool used by those in power to gain control, how technology is used as a distraction, and how knowledge is freedom. Eerily, I think these themes are more relatable and prevalent in today’s society than they ever have been. You will definitely be left reflecting upon the power of knowledge.
  • Incredibly Written – Something that certainly went over my radar as a teenager was the phenomenal writing style of this book. And it will absolutely be something that you appreciate during your rereading. It reads almost in the style of a Brothers Grimm fairytale. Almost poetic and yet so dark.


  • Hard To Follow – Being such an old classic, the language and delivery can be a little hard to get into and follow. It undoubtedly isn’t a light read by any standard and will require a little perseverance to get through.

A Tree Grows In Brooklyn – Betty Smith

A Tree Grows in Brooklyn [75th Anniversary Ed] (Perennial Classics)

A Tree Grows In Brooklyn is a semi-autobiographical novel written by Betty Smith, it was an instant success and has withstood its notoriety throughout the years.

And there’s something about rereading this beautifully written novel that will captivate your heart and mind. Francie has always had to have tough skin. Ever since she was born.

Growing up in the slums of Brooklyn is no easy task, especially when you add all the scandal that follows her family into the mix. From an alcoholic father to an aunt with a habit of serial marriages, drama has always surrounded her.

Throughout this coming-of-age novel, Francie meets a young soldier and it takes all but 48 hours for her to fall head over heels in love. But when he returns home and marries his fiancé before leaving for the war, he leaves her behind heartbroken.

Eventually, Francie finds the company of Ben Blake, a successful boy whom she met during summer school.


  • Key Message – This novel comes with such a life-affirming message that may have gone somewhat undetected during your formative years. It proves that perseverance and hope reign supreme even in the face of adversity and hardship. Even the title itself shows symbolism that even in a tenement district with no light, water, or soil, something beautiful still has the ability to grow.
  • True Love – I also think there are such important themes about love littered throughout this novel that are imperative to our understanding of life and society. True love must be earned and overall trumps society’s standards in terms of social status and reputation.


  • Telling Vs Showing – It does sometimes feel as if you are told a lot of the plot rather than shown it. This can at points make reading a little tedious and less engaging.

The Scarlet Letter – Nathaniel Hawthorne

The Scarlet Letter: The Original 1850 Edition (Nathaniel Hawthorne Classics)

Set in Puritan New England, Hester Prynne gives birth to a baby named Pearl out of wedlock. As her punishment, she must wear a scarlet letter A at all times as a reminder of her adultery.

Hester, who believes she is a widow, is surprised to find out that her husband Roger Chillingworth has arrived back in New England.

And after Hester refuses to name her lover, Chillingworth soon becomes obsessed with learning the identity of this man. This tale tells the story of a self-reliant heroine who is unapologetic about her love regardless of how society views her.

She shows compassion and dignity in her silence which cannot be said for her male counterparts who become crippled by their own guilt and need for revenge.


  • Such Important Themes – I could, as many probably have, write a full-blown essay on the important themes running throughout this book. But it really hit me so much harder during my second read. The idea of forgiveness, consequences of the actions you take, letting personal conviction and not societal norms rule your view of right and wrong, and how hatred can destroy your soul, are all poignant messages that can influence how you go about your life.
  • Engaging Plot – Not only is this book a literary masterpiece in the sense that you could discuss its symbolism and themes for days, but it’s also just really interesting. You can isolate the plot from its poignancy and still consider this one of the best books of all time. From the very beginning of the tale to its ultimate conclusion, you’ll devour through the pages and be engaged and gripped the entire time.


  • Stressful Syntax – What I mean by this is that it is written in complex ‘ye olde’ language that can take a little getting used to – especially if you are used to more modern and current novels.

Beloved – Toni Morrison

Beloved: Pulitzer Prize Winner

Beloved tells the incredible story of Sethe. She was born a slave and escaped to Ohio. Only it’s eighteen years later, and Sethe still feels as much a prisoner as she did all those years ago.

Sethe still mourns the loss of her childhood and is plagued by far too many horrific memories of Sweet Home, that beautiful farm where she was witness to so many atrocities.

And it soon appears that it is not only memories that haunt her home, as so does her child who died nameless. Her tombstone reading but one singular word… Beloved.


  • Historical Fiction With A Powerful Purpose – This devastating and impactful novel though fictitious is based upon real historical events (for even more enormously sad books to break your heart, check out our favorite here). While the real importance of this may have lost on my younger mind, it held a greater deal of weight and significance upon my reread. This is no story with sole purpose of entertainment, it actually really emphasizes the horrors and atrocities of slavery and the irreparable damage it caused not only physically but psychologically too.
  • Highly Emotional – Dealing with such themes as are involved in this novel, you come to expect it to be relatively emotional. But Morrison’s way with words evoked such strong emotions in me. Reading this having had children, it hit me so much harder. Morrison will make you feel things so deeply that it hits your very core. Be sure to keep a pack of tissues with you for this read – you’ll definitely need them.


  • Mature, Graphic, & Potentially Triggering Content – This book tackles some very important issues that are incredibly dark and horrific. They are vital to the tale that is told but the content definitely won’t be appropriate for everyone. These topics may be quite triggering for some people such as the death of an infant, abuse, and rape.

A Raisin In The Sun – Lorraine Hansberry

A Raisin in the Sun

After the loss of their father, the Youngers’ family are set to receive an insurance check for $10,000 from the deceased life insurance policy. And each member knows exactly how they’d like to spend the money.

  • Mama – The mother of the family hopes to fulfil a life-long dream she shared with her husband of owning a large family home.
  • Walter Lee – Mama’s son dreams of investing the money into a liquor store to ensure financial stability for life.
  • Ruth – Walter’s wife agrees with his mother that a home is security but also deliberates because she wants the best outcome possible for her son.
  • Beneatha – Walter’s sister, and Mama’s daughter, Beneatha wants to use the money towards her medical school tuition.

Throughout the story, the family must deal with a variety of issues and conflicts along the way including housing discrimination, racism, and assimilation.

Can the family come together against all the odds and adversaries and fulfil their lifelong dreams?


  • Key Message & Themes – I really feel like the story as a whole is just so much more relatable when you look at it through wiser eyes, but the key messages and themes will definitely resonate with you harder during a reread. The importance of family is something that I always underestimated as a child, but as a mother now, I understand that family is the most important thing in the world. The story also teaches us never to give up on our dreams, something that you should always be reminded of.
  • Great Dialogue – Honestly, Hansberry has just a way with words. And the dialogue throughout this story is phenomenal. It flows so naturally and is so realistic and yet it is so telling. There is so much to be deduced and analyzed from the dialogue in this story and yet it doesn’t feel overdone or too much.


  • It’s All In The Details – This book is so detailed and in some ways this is absolutely a pro. There is so much thought behind every word. But, this does mean that you have to really concentrate on what you’re reading at all times. Missing even the smallest of details can affect the story. This means that you have to keep your concentration levels at optimum the entire way through. You really can’t zone out even for a few minutes.

Final Thoughts

There’s something about being told you have to read a book that makes the experience so much harder.

And let’s face it, during our high school years, we all think we’ve got much better, way more fun things to do with our time than battle through with assigned reading.

And that is probably why these novels just went over our heads a little during our formative years. We weren’t reading for the joy of reading. Or at least, I never was.

I was speed skimming, learning enough of the plot to answer the questions, but ultimately, I was trying to burn through the pages as quickly as possible. But now, it’s all changed.

Maybe it’s because I’m a little older, and a little wiser, and can relate to the struggles of hardship. Now that I have more life experience than just the one break-up with my high school boyfriend. Or maybe it’s because I’m finally reading for myself.

But all I can say is that if you haven’t picked up any of these fantastic reads since high school, if those books are collecting dust in the back of some abandoned cupboard, then it’s time to save them.

I promise that you’ll see these stories in a whole new light, the key messages and themes will speak to you so directly, and you’ll be left with a whole new outlook on life. So pick up your old classics, and fall in love with literature again.

Frequently Asked Questions

What Age Should You Read Classics?

The beauty of books is that there really isn’t an age limit to them, I would say anyone aged 13 above should be able to understand the themes and core messages that make the classics so great.

They are definitely worth a reread once you’re a little older and wiser too.

Are The Classics Still Relevant?

Absolutely. Classic literature is timeless and the key messages and themes continue to be relevant to this day; be kind, forgive, persevere.

Classics highlight our past and predict our futures and teach us about ourselves along the way.

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Noah Burton