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This guide belongs to:

The Great Gatsby Reading and Annotation Guide

belongs to: The Great Gatsby Reading and Annotation Guide The American Dream – Navigating Society and

The American Dream Navigating Society and Morality

Table of Contents

Reading schedules………………………………………………………………………………



Annotation expectations and suggestions……………………………………………………………


Big questions…………………………………………………………………………………….………


1920s contextual overview………………………………………………………………………


Women in the 1920s





Motif Analysis……………………………………………………………………………………………


The American Dream: Creation and Dissolution………………………………………………………


The reading schedules are designed so that you can structure your reading according to your preferences and schedules. We will not be discussing the novel every day in class, so you have some flexibility. Just make sure you pay attention to the due dates! You’ll need to have at a certain amount read for our Socratic Seminars.


If you like to read in larger “chunks,” follow this schedule.

Read/annotate chapter 1 by Tuesday/Wednesday of Week One

Read/annotate chapters 2-5 by Thursday/Friday of Week Three

Finish reading/annotating novel by Thursday/Friday of Week Five

Review and Exam during Week Six

WEEKLY READING SCHEDULE If you like to read with some flexibility, but still want basic


If you like to read with some flexibility, but still want basic guidelines, follow this

If you like to read with some flexibility, but still want basic guidelines, follow this schedule.







Chapter 1-2

Chapter 3-4

Chapter 5 by Thursday/Friday in preparation for Socratic Seminar

Chapters 6-7

Chapters 8-9 – finish book by Thursday/Friday for Socratic Seminar

Review and Exam



If you need a strict schedule to keep from getting overwhelmed in a text, follow this schedule.








Chapter 1



Half of chapter 2



Finish chapter 2




Half of chapter 3



Finish chapter 3



Chapter 4




Half of chapter 5



Finish chapter 5



Chapters 1-5 due for Socratic Seminar




Half of chapter 6



Finish chapter 6



Chapter 7




Chapter 8



Chapter 9



Finished novel due for Socratic Seminar



Review and Exam


Throughout our reading of The Great Gatsby, you are expected to actively annotate the text in addition to synthesizing your thoughts on the novel on the Major Works Data Sheet.

So, what should you annotate? The possibilities are limitless. Keep in mind the reasons we annotate. Your annotations must include comments. I want to see evidence of thinking.

Some general tips:

Have a conversation with the text. Talk back to it.

Ask questions (essential to active reading).

Comment on the actions or development of a character. Does the character change? Why? How? The result?

Comment on lines / quotations you think are especially significant, powerful, or meaningful.

Express agreement or disagreement.

Summarize key events. Make predictions.

Connect ideas to each other or to other texts.

Note if you experience an epiphany.

Note anything you would like to discuss or do not understand.

Note how the author uses language. Try to note the significance of:


effects of word choice (diction) or sentence structure or type (syntax)


point of view / effect


repetition of words, phrases, actions, events, patterns


narrative pace / time / order of sequence of events




contrasts / contradictions / juxtapositions / shifts




any other figure of speech or literary device


reliability of narrator


motifs or cluster ideas


tone / mood






setting / historical period



The most common complaint about annotating is that it slows down your reading. Yes, it does. That’s the point. If annotating as you read annoys you, read a chapter, then go back and annotate. Reading a text a second time is preferable anyway.

Approach the work with an open mind. Let the novel inspire you and stretch your imagination.

If you do this and do it well, you will save yourself the agony of boring literary discussions and the pain of low literature quiz grades.


CHARACTERS As you read, make sure to note characteristics of each of the people you encounter in the novel. What defines them? Do you relate to them? How do they interact?

Nick Carraway: Narrator of the novel. A young man from the Midwest (Minnesota) who moves to New York to work in the bond business after having been educated at Yale and having served in World War I. He is tolerant, open minded, and a good listener. In his own words, he is “inclined to reserve all judgments” (5).

Jay Gatsby: Title character and protagonist of the novel. Also from the Midwest, he moved to Long Island after attaining great wealth and began to throw lavish parties every Saturday with the hopes of attracting Daisy Buchanan.

Daisy Buchanan: Nick’s cousin. Dated Gatsby as a young woman in Louisville, KY, before the war. Married to Tom Buchanan

Tom Buchanan: Daisy’s immensely wealthy husband and an acquaintance of Nick’s from Yale.

Jordan Baker: Daisy’s friend and a professional golfer. She dates Nick during the novel.

Myrtle Wilson: Tom’s mistress and the wife of garage mechanic George.

George Wilson: Tom’s garage mechanic.


Mark passages that help develop the following themes, and add your thoughts analyzing how those passages contribute to the themes.

Positive and negative effects of wealth

Downfall of the American Dream

The burden or vision of the past

Different perceptions of truth

Superficiality and carelessness

Moral and spiritual emptiness

Experience vs. Innocence

Corruption and decay

Appearance vs. reality


Modern Love


Jot down your thoughts about the meanings of the following symbols as you read on post-it notes or in your notes (make sure to keep track of page numbers!) Don’t forget to add what you learn through class discussion and lectures.

The Valley of Ashes

The Eyes of T.J. Eckleburg

Green Light

The Owl-Eyed Man

Gatsby’s Boyhood Schedule

East Egg

West Egg

Colors (white, green, yellow, pink, red, gold, grey, etc.)


MOTIFS: (reoccurring symbolic elements)

Money & material representations of money


Daisy’s voice



The book is divided into nine chapters, usually between 15 and 20 pages each. One way the author frames the scenes is within social gatherings:

Tea party in Chapter I

Party in New York with Tom’s mistress in Chapter 2

Party at Gatsby’s house in Chapter 3

Description of guests at Gatsby’s parties as well as a luncheon with Gatsby in New York in Chapter 4

Tea with Daisy and Gatsby in Chapter 5

Another party at Gatsby’s house in Chapter 6

Another tea at Daisy’s house and a trip to New York in Chapter 7

Gathering at Mr. Wilson’s house in Chapter 8

Funeral in Chapter 9

Another way to frame the story is through the trips to New York taken by the characters: Tom with his mistress; Gatsby and Nick; Daisy, Nick, Tom, Gatsby and Jordan, etc. Between each of the party scenes, Nick usually takes over and describes things or situations. The majority of dialogue comes from the gatherings of people.

SETTING/CHRONOLOGICAL ORGANIZATION The setting is in New York in the 1920’s. There are a few flashbacks to earlier time periods, before the war, which provide contrasting pictures of the characters in terms of where they are now, in terms both of location and emotional status after WWI.

in terms both of location and emotional status after WWI. East Egg  already established wealthy
East Egg  already established wealthy class West Egg  “nouveau riche” – those who
East Egg  already
established wealthy class
West Egg  “nouveau
riche” – those who
weren’t born rich and just
recently came into their
Those living on the West
Egg consider themselves
superior to those with
“new money.” They
adhere to the notion that
true class can only come
from one’s upbringing,
and cannot be mastered
by those who start too
late in life.


Essential Question: How are we shaped by the American Dream?


1. Discuss the title of the book. In what way is Gatsby "great"?

2. An epigraph is a quotation at the beginning of a work that reflects on that work. How does the epigraph to the novel (a quotation by Thomas Parke D’Invilliers – see inside title page) reflect on Gatsby's story?

Characters & Relationships

3. Discuss Nick Carraway's character. How reliable is he as a narrator? What aspects of his character make him an effective narrator?

4. Discuss the relationship between Tom and Daisy. What do they have in common? Why do they stay together? Does their relationship change at all during the course of the novel?

5. Compare and contrast the characters of Tom and Gatsby. In what ways are they similar? In what ways are they different?

6. Compare and contrast the characters of Daisy and Myrtle Wilson.

7. Discuss the relationship between Nick and Jordan Baker. How does it reflect, if at all, on the story of Gatsby and Daisy?

8. Tom and Daisy, we are told, drifted around before settling in East Egg, and Nick expects them to continue to drift. Other characters in the novel, while not drifters, appear to be rootless. How much does rootlessness have to do with the characters' problems, do you think?

9. Nick says that Gatsby "represented everything for which I have an unaffected scorn," and yet he also says that Gatsby "turned out all right at the end," and he tells Gatsby that he is "worth the whole damn bunch put together." With these quotations in mind, analyze attitudes toward Gatsby.

Motifs, Symbols & Themes

10. How does Fitzgerald use Gatsby's parties to present a satirical portrait of the Roaring Twenties?

11. Gatsby's tragedy is that he chooses the wrong dream (Daisy). Has he been corrupted by society? Or is his choice an indication that he is part of the corruption?

12. Once critic has written that "the theme of Gatsby is the withering of the American Dream." Discuss the evidence you can find in the novel to support this contention.



Jay Gatsby spent a number of years trying to establish himself so that Daisy would approve of him. In order to gain the wealth he thought would make him worthy of her, Gatsby became a part of one of the

largest money making endeavors of the 1920s.

bootlegger. The Volstead Act was passed in the summer of 1919. As a result, sale and distribution of alcohol became illegal. The social climate of the era did not respond to this regulation. Many people became

involved in an underground movement to sell and distribute alcoholic beverages. Through these illegal operations, Jay Gatsby was able to obtain enough money to purchase a home just across the bay from Daisy. His mysterious connections with Meyer Wolfshiem leave the reader with questions of the extent of Gatsby's involvement with the attempts to smuggle and consume alcohol in the 1920s.

the attempts to smuggle and consume alcohol in the 1920s. He became a THE JAZZ AGE

He became a


F. Scott Fitzgerald became famous as the chronicler of the 1920s. According to several sources, Fitzgerald named the 1920s the Jazz Age. He was right. Music celebrated the emotions of the people who believed America was at its peak. The snazzy tunes ran through the veins of flappers and their dance partners. The music gave way to freedom, or so it seemed. Men like Louis Armstrong and Duke Ellington began paving the way for exploration in American musical style.


The 1920s in America produced many famous people. Among writers

of the time period, names like F. Scott Fitzgerald and Ernest Hemingway prevail among what became known as "the lost generation." Fitzgerald wrote This Side of Paradise as a portrait of life in the early twenties. In addition, his novel The Great Gatsby portrayed not only lifestyles of the rich during the time period but also lifestyles of the Fitzgeralds during the climax of their life together. Fitzgerald's novel mentions two famous people--Dan Coty and Meyer Wolfsheim. During the time period, there were many famous people. Examples of these are Al Capone, Charlie Chaplin, Henry Ford, Gaston Chevrolet, "Bugs" Moran, and Clara Bow. The Volstead Act of 1919 gave life to such characters as Bugs Moran and Al Capone. One famous, mysterious incident between the two men was the St. Valentine's Day Massacre. The mystery around the murders still provokes curiosity today. In the infant stages of the movie industry, one famous little tramp emerged--Charlie Chaplin. People continue to celebrate the acting abilities he pioneered in the twenties. One other famous person to recognize is Clara Bow. Her perfectly puckered lips became an icon of the age. Music of the twenties produced famous

people such as Louis Armstrong and Duke Ellington.

the time provides us valuable information to reflect on the 1920s.

The American music style became jazz.

These peoples' popularity at


One important symbol in Fitzgerald's The Great Gatsby is the automobile. It represents the reckless convictions of the flapper society. At the beginning of the novel, the reader hears Nick's account of a party where a car wrecks and chaos abounds. Further into the work, Daisy manipulates the automobile to serve her purpose--to escape from Tom and Gatsby. As a result of her careless behavior, Myrtle Wilson dies. Myrtle, too, is reckless. Running in front of a moving vehicle that takes many feet of road to stop because it lacks our anti-lock, power brakes, Myrtle suffers the consequences of

her irresponsibility.

Daisy, as the driver of the automobile, does not suffer the consequences of her behavior. She hides

behind Gatsby, knowing that she does not love him enough to make such a sacrifice for him. The automobile was a dangerous weapon in the hands of carefree, irresponsible people. It still is; Fitzgerald's lesson lives on.


Some of the most exciting and memorable elements of the 1920s in America are the trends.

developed in the 1920s was the Charleston. Other trends in entertainment came in the movie industry. Who can forget talkies and Charlie Chaplin? Further, some of the most famous people of the 1920s were flappers. These women set fashion trends for years to come.

One memorable dance


Symbol or Reality?

Young and fashionable city women expressed their freedom by drinking alcohol freely with men in speakeasies. These women, the "flappers," embodied the disregard for tradition that virtually defined being young and modern in the 1920s. No longer weighed down by long hair and long dresses, or constricted by corsets and rules of propriety, the flappers danced to jazz, drove cars, smoked in public, and appeared to be in no hurry to marry.

Gordon Conway, a Dallas debutante who, at 20, moved to New York and found work as a magazine illustrator, lived the life and promoted the image of the flapper. Her love of parties and fashionable clothes was matched by her drive to succeed in her career. Her later work in theater and film costume design earned her a large salary and an executive position that was unprecedented for women.

and an executive position that was unprecedented for women. Though less educated than Gordon Conway, and
and an executive position that was unprecedented for women. Though less educated than Gordon Conway, and

Though less educated than Gordon Conway, and pursuing no career, F. Scott Fitzgerald's young wife Zelda Fitzgerald became another much admired model for the flapper. Her dazzling dresses, some with hemlines shockingly above the knee, were often the talk of the town. Carefree and daring, she would throw all-night cocktail parties, ride on the hoods of taxis, swim in the public fountains of New York City, and sometimes wear men's knickers. An icon of "flaming youth," Zelda radiated modern beauty.

Scholars have recently shown that the political solidarity women experienced as they fought for the vote led to increased economic independence and educational achievement earlier in the century. However, because this solidarity splintered after women won suffrage in 1920, women suffered a cultural backlash during the 1920s. Moreover, the new freedom the flapper represented had actually first flourished during the war when the rules governing young

women's behavior had been relaxed. As they volunteered for the Red Cross and socialized with soldiers more freely, traditional codes of class division and gender segregation were suspended. And though the liberation from cumbersome clothes and outdated rules was here to stay, the flapper's outrageousness was but an echo of the freedom of movement brought about by the special circumstances of the war.

While more women than ever before pursued careers and higher education throughout the 1920s, they received contradictory pressure to value marriage and domesticity. Some of this pressure came from advertisements that used the image of the flapper in ads proclaiming marriage as the highest possible achievement for women. The message indicated that it was what a woman bought that made her free and modern, not her ability to stand on her own. The truly freewheeling flapper that had first emerged during the war was by 1920 more of a symbol than a reality

POETRY CONNECTION: DOROTHY DOW CABARET As published in Will-o’-the-Wisp, 1925 Dorothy Dow was a popular
As published in Will-o’-the-Wisp, 1925
Dorothy Dow was a popular poet writing in Chicago
during the 1920s-30s. She frequently wrote about party
scenes popular among the young rich, and her poetry
captures both her admiration for the lifestyle of the
“flapper” and her awareness of its innate superficiality.
As you read her poem, “Cabaret,” consider how she
describes the young woman at the nightclub. How does
she contrast the glittering scene with negative imagery?
How does the tone of the poem change or intensify in
the last two lines?
Her dress was bistre, and her eyes, slim lines
Of grey jade gleaming through a blackened veil;
Glad laughter, gayer than a madrigal,
Shattered, as wind, against a spray of vines,
The dark and mournful beauty of her small
Vermilion mouth, that ached with being gay.
And subtly, dreadfully, there lay, in all
The odor of fruit over-ripe…


A symbol is a concrete object or an idea that has its own meaning but is used to suggest another. Match the following the following objects ideas with one of the symbolic explanations found below. Include one example from the novel to demonstrate your answer.

Valley of Ashes / Green Light / Eyes of Dr.T.J. Eckleburg / Automobile / East Egg / West Egg / Owl-Eyes / Gatsby’s gold tie and silver shirt


Symbolic Significance

Example (including page reference)


Wisdom; the ability to beyond appearances.



Omniscient power, aware of everything. God is dead.


Poverty; barrenness; hopelessness.


Pretentious. Glittery, but really an imitation


Destruction and recklessness.


Wealth and material excess.


Fashion, affluence. Old money and values.


Invitation of false hope.



Motif: a theme that is developed and repeated in a work of art.

Wealth and/or money being the seed of corruptions is a prevalent motif in The Great Gatsby. Not only does wealth distinguish various characters, but it also blinds them from reality. Examples of this motif are hinted at below. Find them in the novel and then include a brief explanation that demonstrates an analytical understanding.

pg. 1 The advice Nick receives from his father:

• p g. 1  The advice Nick receives from his father: • pg. 68 

pg. 68 Gatsby’s run in with the police:

father: • pg. 68  Gatsby’s run in with the police: • pgs. 64-67, 88, 93-96

pgs. 64-67, 88, 93-96 The root of Gatsby’s wealth

pgs. 64-67, 88, 93-96  The root of Gatsby’s wealth • pg. 92  Gatsby and

pg. 92 Gatsby and his shirts

of Gatsby’s wealth • pg. 92  Gatsby and his shirts • pg.153  Gatsby’s po

pg.153 Gatsby’s pool

wealth • pg. 92  Gatsby and his shirts • pg.153  Gatsby’s po ol •

Find one additional example:

wealth • pg. 92  Gatsby and his shirts • pg.153  Gatsby’s po ol •


“The American Dream” is the notion that in the USA success and material prosperity are available to all. The youthful generation of the Jazz Age subscribed to this dream more so than ever before in American history, and the characters of F.Scott Fitzgerald’s novel, namely Jay Gatsby, are no exception. Unfortunately, they also reflect the fact that the dream can easily turn into a nightmare.

The Creation of the Dream:

Locate the passages below and in a sentence or two relate each to the beginnings of Gatsby’s dream:

1. Ch. 5, p.91 “He hadn’t once ceased looking at Daisy…”

2. Ch. 5, p.92 “If it wasn’t for the mist we could see your home…”

3. Ch.5, pp. 95-96 “As I went over to say good-by I saw that the expression…”

4. Ch. 6, p. 98 “I suppose he’d had the name ready for a long time…”

5. Ch. 6, pp.109-111 “He wanted nothing less of Daisy than she should go to Tom…”

The Shattering of the Dream:

Locate the passages below and in a sentence or two relate each to the end of Gatsby’s dream:

1. Ch. 8, pp.152-162 “It was dawn now on Long Island…” to the end of the chapter.


Ch. 9, pp.179-180 “Gatsby’s house was still empty when I left…” to the end of the chapter.

Conclusion: Complete this idea in three to four sentences.

In my opinion, Gatsby’s mistake was:

Novel Reflection: How does The Great Gatsby connect to our essential questions? Do you find the novel’s ending hopeful or depressing? How is this novel still relevant to us as modern readers?

This reading guide was created by Dara Miller, English teacher at the Chicago High School for the Arts. Some materials adapted from Cambridge Public Schools, The University of Texas at Austin, NoveLinks, and Montgomery County Public Schools.