The Great Gatsby


Many people describe THE GREAT GATSBY as boring and overrated. 

They’re wrong.

But it does take some life experience and an intimate familiarity with pain to understand the book. Apart from F. Scott Fitzgerald, the two men who knew the book best considered it a masterpiece. They were two of the most badass writers of the 20th century, and they both blew their own brains out. This episode of LIT AF looks at THE GREAT GATSBY through the eyes of Hunter S. Thompson and Ernest Hemingway. 

Intro to The Great Gatsby

LIT AF Season 1 Episode 1


The New Guy In Town

LIT AF Season 1 Episode 2

Chapter 1 of The Great Gatsby

Meet the new guy in town. Narrator Nick Carraway introduces us to Tom, Daisy, and the man himself in Chapter 1 of The Great Gatsby.


Have What You Want / Want What You Have

LIT AF Season 1 Episode 3

Chapter 2 of The Great Gatsby

Did school teach you to achieve your goals, or just keep setting new ones to make yourself constructively miserable? Philosophers, drug dealers, and late stage capitalists all know the  secret – you’re never going to be happy as long as you want what you don’t have. Welcome to Chapter 2 of The Great Gatsby.


I Am Because We Are

LIT AF Season 1 Episode 4

Chapter 3 of The Great Gatsby

Many people talk about Gatsby’s parties, and how he used them to lure Daisy – but there is more to partying than meets the eye. What attracts us to each other? Can we account for this with attachment theory, or neuromodulators? Is it just dopamine, serotonin, testosterone, or estrogen? We know isolation is problematic, but we’ve also made relationships complicated – when is relying on another person a good thing, and when does it become a warning sign? Speaking of dependence, what impact/s do substances like alcohol and drugs have on our interactions? All this and a driving lesson in this week’s episode.


You Don’t Know Me

LIT AF Season 1 Episode 5

Chapter 4 of The Great Gatsby

Chapter 4 begins with young ladies making wild guesses about Gatsby. He’s a killer. He’s second cousin to the devil. When we don’t have information, we make assumptions. When we have a little information, we go way positive or way negative. If you don’t believe me, have a look at online reviews. At one level, these schema (categories of thinking) can help us when we encounter new situations. However, when our inner ideas about people get loud enough to drown out the information right in front of us, they become ISMS (racism, sexism, ageism, etc.). Just look at how Fitzgerald describes Black and Jewish characters later in the chapter.


Better Pearls, Better Swine

LIT AF Season 1 Episode 6

Chapter 5 of The Great Gatsby

We are now over the halfway point of the book. It’s worth remembering how most people encounter Gatsby the first time. However amazing they may be, most high school students simply don’t have the life experience to understand what some of these characters – and definitely the author – are experiencing in their lives and marriages. And, not for nothing, school is the most toxic brand in history, so selling this as a reading experience is an even taller order. Fortunately, we don’t have those problems. And everyone of every age can understand what a nervous fuck-up Gatsby becomes when he finally has his secret meeting with Daisy.


Groundhog Gatsby

LIT AF Season 1 Episode 7

Chapter 6 of The Great Gatsby

“Can’t repeat the past?” he cried incredulously. “Why of course you can!” 


Baby You Can Drive My Car

LIT AF Season 1 Episode 8

Chapter 7 of The Great Gatsby

Daisy said she never loved Tom. But then she said she did. Tom says he loves Daisy. But he was diddling Mrs. Wilson. Gatsby does seem to really love Daisy.  He shouldn’t have let her drive. By the end of this chapter, Mrs. Wilson is dead, Tom is grieving, and Gatsby is keeping watch over Daisy’s house. But accidentally homicidal Daisy is now depending on Tom, and it’s starting to feel like Gatsby’s love affair is losing the light faster than a hot summer afternoon at the Plaza.


Fall Is When Things Die

LIT AF Season 1 Episode 9

Chapter 8 of The Great Gatsby

Most of THE GREAT GATSBY is timeless. Love and the nutty things we do for love happens in/to every generation. It has for centuries, and it will until we cook ourselves off the planet. Fitzgerald focuses on the characters, the immediate settings, and the dialogue without much connection to real people or events that would locate the book in time. Apart from scattered, vague references to the war, the world series scandal, and prohibition, there isn’t much to suggest this story couldn’t happen in any era. Like, now. But Fitzgerald does pay close attention to one element of time: the seasons of the year. The plot begins in spring (season of re/birth and renewal), hits its peak in the summer (heat can be passionate or fatiguing), and now, in the penultimate chapter, we find ourselves at the beginning of fall. Fall is when things die.


It’s All Over

LIT AF Season 1 Episode 10

Chapter 9 of The Great Gatsby

Gatsby is dead and no one is coming to his last party. All that’s left for us is to figure out where we belong, and whether we are living in the past, present, or imagined future.