The Personal Canon: Core Works of Art We Return to Time and Again for Inspiration

By Jon Gorey, Drew Housman, and Trent Hamm

There’s something beautiful about the idea of refining an experience — that you can take the same walk to work every day, but improve what you get out of it each time. Maybe you learn to distinguish the different bird calls, or you start to identify the trees you see, or you discover the incredible history behind the corner bakery and its 80-year-old owner. The familiar can become new again or reveal even deeper beauty when you approach it with an open mind.

We at the Simple Dollar are always looking for ways to appreciate, improve, and build upon what we already have, as opposed to seeking out (and shelling out for) the newest, shiniest thing. It’s a valuable exercise to reconsider and appreciate what you already have – and this is especially true when it comes to art.

There are certain movies, books, poems, and paintings that are worth spending some time with. Re-watching, re-reading, and re-contemplating quality works can be very rewarding experience. You’ll often catch things you didn’t appreciate the first few times around, finding greater wisdom or humor each time. Referring back to your favorite works of art can help to anchor you in times of distress, and to inspire you in times of complacency.

Here are some core works of art that help to keep us motivated, curious, and enthralled, year after year.

Jon: Ferris Bueller’s Day Off and Catcher in the Rye

My stack of books to read is tall and wobbly — a leaning tower of literature I can’t seem to keep up with. Our Netflix queue, meanwhile, is overloaded with Oscar-winning movies from seven or eight years ago we still mean to watch. And yet, now and then I’ll bypass the book pile in favor of a novel I’ve read five times already, or pop in a DVD I’ve watched dozens of times. When it comes to culture, sometimes I just want a wise old friend, not a new relationship.

It can be a struggle to choose between re-watching a favorite film you know to be great and taking a chance on a new one, says Robert Thompson, trustee professor and founder of the Bleier Center for Television and Popular Culture at Syracuse University. “There’s one argument that you should just pick the really good stuff and just keep watching and reading it over and over again,” Thompson says. “But there are so many great works of art out there that we can only begin to scratch the surface.”

With so many new critically acclaimed films, books, and TV shows coming out all the time, Thompson says it’s hard to find a balance when there are only so many hours of the day to consume culture – and so many years in your life. “I remember that horrible moment in my mid-40s when I realized not only all the great books I would never write, but all the great books I’d never even get to read,” he says.

But Thompson says there is a value to revisiting a fine work of art — that the more times you see it, the more you get out of it. “I don’t care how many times you watch a production of Hamlet, you always find more in there. To read the Divine Comedy once, to look at the paintings in the Sistine Chapel once, is to have experienced them — but it’s certainly not close to getting everything there is out of them,” Thompson says. “The good stuff just keeps on giving.”

This isn’t just true for masterpieces, Thompson says. “I’ve seen Animal House and Fast Times at Ridgemont High, what, maybe 60 times while teaching them over the years? And I still find things,” he says. And some works simply become part of our rituals. “The first time people saw It’s a Wonderful Life, they wept. And now that they’ve watched it 25 Christmases in a row, it’s like a longtime marriage instead of a first date — and both of those have their value.”

I was glad to hear that, because after giving it some careful thought, I realized the works of art I revisit most often — besides my favorite albums, of which there are simply too many to write about — aren’t exactly Shakespeare. There’s the 1986 John Hughes film Ferris Bueller’s Day Off and the 1955 book Catcher in the Rye by J.D. Salinger. And to be honest, I should probably add the 1993 Richard Linklater film Dazed and Confused to this list, too.

I know, I know: It makes me sound like a juvenile slacker stuck in a state of perpetual adolescence or something. And maybe I am. But for whatever reason, those coming-of-age tales are the works I return to again and again.

I’ve come to realize the common thread between all three is that they’re slice-of-life, in-the-moment narratives. Unlike epic sagas that unfold over years or generations, these three stories take place over just a single day or two.

And I think that’s what really resonates with me. There is so much to see, do, learn, and experience in a single day; entire novels may be lurking in a Tuesday. Every day is rich with opportunity, but too often we let one slide by until the days blur into a month or year or a lifetime squandered.

Like the longtime marriage Thompson speaks of, I find deep comfort in these familiar stories and characters. I also think they help me to reset my inner compass, so to speak. Ferris Beuller’s brazen, carpe-diem optimism and Holden Caulfield’s restless but incorruptible sincerity remind me of the core beliefs I forged as young adult — and desperately strive to hold onto, even as the adult world so often tramples on such values.

And Catcher in the Rye, like It’s a Wonderful Life, is something of a Christmas story. As such, I tend to revisit it around that time of year, almost like a holiday tradition. I’m especially prone to re-read it if I’m visiting New York, because while parts of Salinger’s Manhattan may be long gone, he immortalized for me the irresistible romance of the city in December.

Oddly enough, Holden himself saw the virtue in revisiting something you’ve already experienced a number of times. Here he is describing why he liked returning to the Museum of Natural History (though after this passage, he decides not to go in):

“The best thing, though, in that museum was that everything always stayed right where it was. Nobody’d move. You could go there a hundred thousand times, and that Eskimo would still be just finished catching those two fish, the birds would still be on their way south, the deers would still be drinking out of that water hole, with their pretty antlers and their pretty, skinny legs, and that squaw with the naked bosom would still be weaving that same blanket. Nobody’d be different. The only thing that would be different would be you. Not that you’d be so much older or anything. It wouldn’t be that, exactly. You’d just be different, that’s all. You’d have an overcoat this time. Or the kid that was your partner in line the last time had got scarlet fever and you’d have a new partner. Or you’d have a substitute taking the class, instead of Miss Aigletinger. Or you’d heard your mother and father having a terrific fight in the bathroom. Or you’d just passed by one of those puddles in the street with gasoline rainbows in them. I mean you’d be different in some way—I can’t explain what I mean. And even if I could, I’m not sure I’d feel like it.”

That’s what I enjoy most about going back to these works: I’m a little different each time. As I got older, I could better see both the earnest heroism and confused folly in Holden’s behavior. As a writer, I continue to find new brilliance in Salinger’s unrivaled ability for dialog. And as a parent, I’ve grown to adore Holden’s little sister Phoebe, and his sweet relationship with her.

To paraphrase the sleazy Wooderson from Dazed and Confused: “That’s what I love about these stories. I get older, they stay the same age.”

–Jon Gorey

Drew: The Right Stuff and Illmatic

The Right Stuff, a work of historical nonfiction by Tom Wolfe, details the lives of the astronauts who were vying for a spot aboard the first U.S. space shuttle that would leave earth’s atmosphere. It’s a compelling read, especially for someone who didn’t grow up during the Cold War and has a hard time appreciating just how much the space race meant to the United States at that time.

What really struck me on my most recent time through the book was the single-minded focus of each astronaut the books profiles. They put family obligations, other ambitions and even their personal safety on the back burner. All that mattered was winning a spot on the Mercury shuttle.

There were no side hustles. No plan b’s. No “parachutes” for their careers, literally or figuratively. I admire the tenacity of anyone who approaches their work in such a fashion. If you are sure you want something, there’s no better way to approach it than to go all in.

That being said, this attitude is not the only way to approach your career. I was left thinking about how I don’t have anything in my career I care about to the point where I would leave my girlfriend for it. And I certainly wouldn’t die for my job.

Instead of wondering if there was anything out there for me that I would abandon everything for, the book made me think about how it’s okay to not be in love with your career. I have time to be a well rounded, well read, thoughtful person. This is in contrast than some of my peers who spend every waking moment chasing a singular passion.

Trying to learn and experience many different things has it’s own benefits, even if you never become world renowned in any one of those fields. I like that I can read The Right Stuff and marvel at the astronauts while also appreciating that I can live a satisfying life without seeking fame and glory by riding a rocket going 17,000 miles per hour.

Another work I return to often is Illmatic by Nas. It’s one of the most lauded hip-hop albums of all time, and for good reason. It’s poetry at its finest: evocative, moving, and inspirational. Nas was only 18 when he recorded this album about what it’s like to grow up on the streets of New York City in the 1980s, yet his words contain the wisdom and thoughtfulness of a Buddhist monk.

He tackles a range of issues on the album, and many of them are heavy and sobering: references to police brutality, gang warfare, the prison system, drug use, prostitution, and poverty abound.

Yet, the more I listen to it, the more I’ve been tuning into the fact that Nas seems to be having so much fun while he’s rapping. He makes jokes. He invites his friends to randomly shout on a chorus. He laughs. He talks about partying. He references Disney’s Cinderella, for crying out loud.

This lightheartedness in the face of adversity has been on my mind lately, especially as is it relates to personal finance. I tend to be very hard on myself if I don’t hit my savings goals, or if I buy blueberries at one market and then realize they were cheaper at another market. (“That $1.25 I just wasted could be worth $30,000 when I turn 60 if I’d invested it! Arghhh!”)

Thinking about ‘Illmatic’ helps me to keep things in perspective. I’m safe. I have a stable job and I’m surrounded by people who love me. If something happens that’s not perfect, there’s no need to freak out. When I get frustrated, It helps me to imagine a young Nas looking at me and saying “man, I made a great work of art while dealing with life in a public housing project in one of the most dangerous cities in the country. Chill out.”

–Drew Housman

Trent: Self-Reliance and Bedroom in Arles

When Jon asked me to talk about the core artistic works that have kept me motivated, curious, and enthralled throughout my life, two such works immediately came to mind.

The first is Ralph Waldo Emerson’s essay Self-Reliance, which I wrote about extensively on The Simple Dollar in a three-part article. The thoughts that flow through this essay have helped me to get through almost every challenge in my life, from the professional challenge of entrepreneurial ventures and a politically-charged workplace to personal challenges like the unexpected death of a dearly-loved mentor. In those moments of challenge, it is so easy to fall into a trap of finding excuses and blaming others when, in the end, my feelings and my choices are my own responsibility and no one else’s. Emerson enriches that core idea of self-reliance with the beautiful yet slightly archaic tone of mid-19th century American English, with words that feel like arrows shot across the ages directly into my heart.

I read Emerson’s words often.  That essay is a part of a very dog-eared collection of Emerson’s writings that sits on my bookshelf, right next to me each day as I work.  I pull it off that shelf quite often, flipping through the various essays but inevitably finding my way right back to Self-Reliance.

The other work is Vincent van Gogh’s Bedroom in Arles, specifically his second version of that painting which currently resides at the Art Institute of Chicago. This painting captures a very small bedroom of a man with a relatively simple life in terms of his possessions, but there is such brightness and life throughout it.  There is a blue sky and rich sunshine behind those windows. There is simple comfort in that bed. There is a chair upon which to sit and read and write letters.  There are bright colors throughout all of it, reflecting the joy that is to be found in such a life.

Whenever I think of a place I would love to escape to for a day or two, this is it. A little, quiet, simple room without much upkeep, with a simple, comfortable bed, a table with a book I’ve been dying to read and a pitcher of ice-cold water and a glass nearby, and warm morning sunshine flowing in through the window, perhaps with a gentle breeze that beckons me to go outside and explore.

–Trent Hamm

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What films, movies, books, or albums do you find yourself returning to? Share yours in the comments.

Trent Hamm

Founder & Columnist

Trent Hamm founded The Simple Dollar in 2006 and still writes a daily column on personal finance. He’s the author of three books published by Simon & Schuster and Financial Times Press, has contributed to Business Insider, US News & World Report, Yahoo Finance, and Lifehacker, and his financial advice has been featured in The New York Times, TIME, Forbes, The Guardian, and elsewhere.