Overview

This five-week course examines F. Scott Fitzgerald’s The Great Gatsby (1925) as a distinctive and provocative entry in the American gangster fiction tradition. This course asks students to consider how Gatsby inhabits and complicates the genre, offering a story in which the gangster is not simply a criminal protagonist but a symbol of the American Dream itself. Through close reading, literary analysis, and contextual discussion, learners will explore how Fitzgerald uses character, language, structure, and symbolism to depict ambition, identity, class, and the limits of self-invention in Jazz Age America. Learners will interact with The Great Gatsby as an enduring work of American fiction that uses the figure of the gangster as a lens through which to examine the hopes and failures of American life. Centered on F. Scott Fitzgerald’s 1925 novel, the course situates the novel in its historical moment (notably, Prohibition and the Jazz Age) while examining the literary craft that has made it one of the most studied novels in the American canon. Students will investigate character complexity, poetic and vernacular language, symbolism, narrative structure, and the concept of the ineffable—those things that resist being put into words but that drive human longing. Designed for three distinct learning tracks—Academic/College Student, Book Club Leader, and Creative Writer/Artist—the course also addresses the role of AI and popular culture as tools for engaging with literature, encouraging students to bring their full selves to the text and to carry what they learn beyond the page.

Syllabus

Approaching Gatsby

Week one introduces students to the course structure, the three learning tracks, and the role of AI and popular culture as tools for engaging with literature. It situates The Great Gatsby within the gangster fiction genre—comparing its opening chapter with W.R. Burnett’s Little Caesar—and provides essential biographical and publication context for Fitzgerald and the novel.

The Great Gatsby in the World

Week two builds the historical and cultural context necessary for reading The Great Gatsby as a gangster novel. Students will examine the social forces of diversity, Prohibition, and the Jazz Age, explore the specific gangster elements embedded in the novel (rum running, Arnold Rothstein, bootlegging operations), and analyze the symbolic ways the novel draws on gangster fiction tropes—including meretriciousness, marital affairs, moral ambiguity, and violence.

The Characters of The Great Gatsby

Week three undertakes a close examination of the novel’s five major characters: Nick Carraway, Jordan Baker, Tom Buchanan, Daisy Buchanan, and Jay Gatsby. Students will analyze how Fitzgerald constructs character through selective detail, imagery, contradiction, and gradual reveal, and will consider how each character embodies and complicates the novel’s central themes of ambition, class, identity, and moral compromise.

Language, Symbolism, and Structure

Week four examines the craft elements that give The Great Gatsby its distinctive texture and depth. Students will analyze Fitzgerald’s dual register of poetic and vernacular language, explore the roots of the English language (Germanic vs. Latinate diction) as a creative tool, examine the novel’s major symbols (Eckleburg’s eyes, the valley of ashes, the green light, the Queensboro Bridge), and analyze the structural choices—geographic movement, parallel chapters, unreliable narration—that shape the reader’s experience.

Beyond the Text — The Ineffable and Application

Week five steps back from close reading to examine two larger questions: What is The Great Gatsby ultimately trying to do as a work of art—and what does it mean to read it as a gangster novel? Students will explore the concept of the ineffable (that which cannot be put into words) as a key to understanding the novel’s deepest ambitions, reconsider who the ‘real’ gangster of the novel might be, and engage with the novel’s closing passages as an invitation to reflect on their own lives, ambitions, and the stories they tell about themselves.