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Three Books that Helped Define a Generation


Millennials take note, these novels all have themes that still ring true today.

With summer finally here, it’s a great time to catch up on some of the books piling up on your nightstand (or add a few more you weren’t planning on reading). One of my favourite things about reading older books is that they offer a glimpse of the social atmosphere at the time, and I’m not just talking about non-fiction. Fiction writers, as shown here, are very often crafting stories out of real life. You’ve probably heard the term “book that defined a generation” but I’d argue books are also defined by their generation.

This is such a list. A group of books that helped define their times. Whether they set out to achieve this or not, I believe each of these authors helped define their generation or at least how we now perceive their generation. I’m not talking about the sweeping stereotype kind of definition either, they helped define by describing, almost perfectly, a particular way of life or a subculture, while making assertions about how these groups fit into society at the time.

It’s easy to get stuck focusing on the difficulties we as millennials face today, but past generations have struggled with many of the same things that we deal with in the present – including lack of direction, difficult career choices and even the desire to be taken seriously. You probably roll your eyes when someone says “when I was your age…” but as these books point out, other generations have faced similar challenges (so maybe there’s something to all that advice after all).

The Sun Also Rises (1926)
The Sun Also Rises

Published in 1926, The Sun Also Rises is Ernest Hemingway’s debut novel, though perhaps not his most famous. The book explores the lives of American and British expatriots living in Europe (specifically Paris, France and Pamplona, Spain) in the years after World War I.

A love story at heart, it’s easy to stay focused on Hemingway’s descriptions of café life in Paris and the bull fights of Pamplona, but the real emphasis should be placed on the social themes of a generation that grew up in the shadow of war. This is the same generation that Gertrude Stein famously coined “the lost generation.” This isn’t about being hidden or invisible to the rest of the world but more about a generation that lacked direction and was drawn to wandering. While the story was published almost 90 years ago, many of the major themes should still resonate with millennial readers.

On The Road (1957)
on the road editions

Jack Kerouac’s formative novel about a young man setting out west has been a traveler favourite for decades. However, the novel has not only been influential for those looking for adventure, it helped define the beat generation of the 1950s. The beats were specifically Americans, who explored new ideas of culture, spirituality and sexuality, while (of course) rejecting the traditional values of the day.

Kerouac’s On The Road follows him and fellow beat generation notables including Allen Ginsburg and Neal Cassady (known as Dean and Carlo in the book) as they try to find something meaningful ‘out there.’ There are themes here that many millennials will identify with including friendship, travel, loss and the search for purpose or ‘it.’

Kerouac famously wrote the novel on a long scroll of paper, with all the real names still in-tact. It’s a much harder read but if you’ve already read On The Road, I’d suggest going back and finding “The Original Scroll” edition (pictured above), which has recently become available.

Less Than Zero (1985)
less than zero

In my opinion, this is one of the quintessential Gen-X novels but its themes are still staggeringly present today, especially in our culture’s obsession with celebrities.

Published when author Bret Easton Ellis was only 21, this is a novel about the high-life of the 1980s as seen through the eyes of a student returning home to Los Angeles for winter break. The novel remains the most controversial of these picks for the way it handles themes of drug use, prostitution and partying in young, affluent Americans.

If you’ve ever felt disconnected from the place where you grew up, your old friends, even your parents, Less Than Zero will read like a manual on detachment. Do yourself a favour and try to avoid the Andrew McCarthy/Robert Downey Jr. movie until you’ve read the book, or at least understand that it does not follow the novel in most places.

In creating this list, I wanted to focus on three books that I’ve read, own and consider some of my favourites. But it’s in no way a complete list. What would you add to the list? Who and what are your favourite authors and books that you feel helped define their generation?


Christopher is Co-Founder and Managing Editor at The Reply. He has a fondness for strong coffee, good books and foreign news services. When he was five years old his father helped him raise a family of chipmunks over the winter, you should ask him about it. Professionally, he’s spent time as a technology journalist, PR consultant, and freelance blogger. Christopher’s work has appeared in a lot of trade magazines you’ve probably never heard of and maybe some you have. He has a B.A. in Political Science from the University of Toronto and a certificate in Media Foundations from Humber College in Toronto.