Everything I Know About Money I Learned from Pop Culture

Since early childhood, I have been an avid consumer of pop culture. Whether it’s chewing gum jingles from the 1980s, movies I watched on an infinite loop in high school, or viral memes from the 2010s onward, my brain has become a vast storehouse of random pieces of entertainment that briefly held the zeitgeist’s attention.

(Side note: This commitment to random pop culture often shows itself in myriad ways that become predictable to those who live with me. For instance, anytime I am making toast, one can hear me mutter, “Xeno! Xeno with the toast family!” Similarly, if a recipe calls for pepper, I will pretty much always say, “Waiter! There is too much pepper on my paprikash!” And of course, if someone asks me to hand them the Aveeno Daily Moisturizing Lotion, I can be counted on to remark, “It rubs the lotion on its skin…” as I pass the bottle along.)

Considering just how important pop culture is to my understanding of the world, it should come as no surprise that much of my early conception of money was also shaped by the media I consumed in childhood and early adulthood.

Here are financial lessons I learned from pop culture—the good, the bad, and the ugly:

The Pop Culture: The Westing Game by Ellen Raskin

The Lesson: How to “play” the stock market

One of my favorite books when I was in elementary school was The Westing Game by Ellen Raskin. This novel tells the story of Westing Paper Products tycoon Sam Westing and his unusual will. After his death, Westing’s lawyers invite 16 tenants of Sunset Towers to the reading of his will, which starts a mysterious game. The heirs are paired off and each given $10,000 and an envelope of clues and invited to solve the puzzle of who has taken Sam Westing’s life.

Though it’s an ensemble cast, I always considered 13-year-old Turtle Wexler to be the protagonist. She’s entrepreneurial, funny, smart as a whip, and takes no guff from anyone. Turtle decides that the baffling clues are actually stock symbols. With the help of her partner, 60-year-old dressmaker Flora Baumbach, Turtle invests the $10,000 in the stocks “named” by their clues, as well as Westing Paper Products (stock symbol WPP).

Her investment pans out, and Turtle is delighted to share that the $10,000 stake has grown to $11,587.50 by the end of the game several weeks later.

Something that I really appreciated about Turtle’s characterization was how confident she was about investing (even though she had the normal 13-year-old’s insecurities about boys, hair, her sister, and the like). Though I do not invest in individual stocks, Turtle’s example is exactly how I would do it. Here’s what she did:

  1. Invested money she could afford to lose. Neither she nor Flora needed the $10,000.

  2. Picked stocks she believed in. Turtle’s belief in the clue stocks was based on her assumption that Sam Westing was a genius and his clues meant something specific about the stock market. He was a genius, but she was not necessarily on the right track with those investments

  3. Changed tactics when learning new information. When the clue stocks don’t perform as well as Turtle would like, she puts all the money in Westing Paper Products. She has been reading about how the company is doing in the Wall Street Journal and paying attention to how the WPP stock is faring.

  4. Created an informal “limit order.” Turtle can’t handle the buying and selling herself since she is only 13 years old, so she enlists Flora to do it for her. There is a point when Flora wants to sell their stocks since they are up, but Turtle asks her to wait until the price reaches a specific level. This sets up what amounts to a limit order, ensuring they don’t miss out on growth by selling too soon or risk losing their gains by waiting too long to sell.

Ellen Raskin includes an epilogue that shows how all the characters fare over the coming decades. What stuck with me from that story coda was the description of how Turtle—by then known as T.R. Wexler—makes millions in the stock market, loses it, and then makes another $5 million. This small portion of the end of the book helped me understand market volatility better than any dry explainer ever could.

The Pop Culture: Trading Places


The Lesson: How a short sale works

In Trading Places, the racist, classist, jackass Duke brothers make a bet that they can elevate a homeless grifter (Eddie Murphy’s Billy Ray Valentine) to the highest level of their hedge fund while making one of their best employees (Dan Ackroyd’s Louis Winthorpe) lose everything and become homeless himself. When Valentine and Winthorpe find out what the Dukes have done, they devise a plan to completely wipe out their fortune via a short sale.

The Dukes have bribed an official to get an advance copy of the government report on the orange crop. This report says that the orange crop is strong, which means the future price of concentrated orange juice will fall, since there is a good supply of the fruit from this crop. But Valentine and Winthorpe intercept the real report and substitute one that says the crop is doing poorly. If that were the case, the future price of OJ concentrate would go up, since there wouldn’t be enough supply.

The Dukes think the crop has failed, so they drive up the price of OJ futures, intending to sell their stocks at exorbitant prices after the official report comes out. Valentine and Winthorpe promise to sell OJ futures at a high price during this madcap buying frenzy—which is interrupted by the Secretary of Agriculture releasing the official report saying the crop is strong. This means the futures are not worth nearly as much as everyone just paid. Valentine and Winthorpe gleefully agree to purchase OJ futures at a fraction of the price they just sold them for.

My repeated viewing of this film as an impressionable child was invaluable during the Gamestop short sale kerfuffle in 2021. I understood that taking shorts against a company (which was what the hedge fund managers were doing with Gamestop) means that you are selling shares you do not currently own in the anticipation that the price will fall. You will then buy the shares at the lower price to "cover" your original sale. This is basically the same buy-low-sell-high strategy that is the backbone of trading, but simply done in reverse order.

Fun fact: at the time that Trading Places came out, it was not illegal to trade commodities based on inside information you got from the government. As shady as the Dukes and Valentine and Winthorpe appear (which is what you look like when you meet a guy in a dark parking garage and/or disguise him as a gorilla), everything they did on the trading floor was completely legal at the time of the film. It wasn’t until 2010 that this was banned in a provision known as the Eddie Murphy Rule.


Additional fun fact: I didn't know what a bookie was when I saw Trading Places as a kid, so I figured out how a bookie works based on seeing how Wall Street brokers in the film worked...

Milliped CC BY 3.0

The Pop Culture: The Big Lebowski


The Lesson: Always do your due diligence

During my final year of college, The Big Lebowski was the only DVD I owned. I would watch it with the French subtitles turned on when I was procrastinating because then I could pretend it was helping me study for my French literature classes. (I do know how to say “You see what happens, Larry? You see what happens when you [FIND] a stranger in the [ALPS]?!” in French because of this habit).

And while there are any number of important life lessons in this stoner’s noir odyssey, including the importance of being careful when a beverage is present, the legality of keeping an amphibious rodent, for ya know domestic…within the city, and how not to respond to the Malibu Police Chief when he asks if he has made himself clear, I think the film best illustrates why it is vital to do some research when large sums of money are involved.

If it’s been a few years since you’ve seen this classic, the story revolves around Jeffrey “The Dude” Lebowski being mistaken for a millionaire also named Jeffrey Lebowski. When the big Lebowski’s trophy wife Bunny is kidnapped, Dude is tasked with handing off the $1 million in ransom money to the kidnappers. The Dude unintentionally hands off a ringer before his car is stolen, with the big Lebowski’s ransom briefcase still inside.

By the end, Dude learns that the big Lebowski actually has no money of his own, the briefcase he was given was full of phone books (which meant he threw a ringer for a ringer!), and Bunny had never even been kidnapped.

Though I love this movie beyond all reason, I have always been rather irritated at Dude for not opening the briefcase the big Lebowski gave him—even though it would have ended the movie right then and there. But seriously, who wouldn’t want to feast their eyes on $1 million in cash?


Had the Dude simply opened the briefcase while still in the presence of the big Lebowski, he would have immediately known that he was being sent on a fool’s errand and that the big Lebowski was planning to pin the loss of the money on him.

Alternatively, if he had spent a little time finding out more about the big Lebowski, he would have learned the man had no wealth of his own, so he would have been more cautious about accepting the job as ransom courier.

While I want to cultivate the abiding nature of the Dude in some areas of my life (because sometimes all you can do is say “Eff it. Let’s go bowling.”), in the realm of finance, the message is clear: don’t be like the Dude. Always do your due diligence when you’re handed a cool million.

The Pop Culture: "Material Girl" by Madonna


The Lesson: It’s a privilege to reject material things