Both The Beautiful and Damned and The Great Gatsby are novels about a male protagonist's existential struggles and eventual downfall. Both works explore the societal concept of the American Dream through the lens of 1920s Modernism. The Great Gatsby acts as a cautionary tale of rags to riches as Jay Gatsby succeeds in making his fortune but fails to feel satisfied. The Beautiful and Damned is a riches to rags story, where wealthy heir Anthony Patch's marriage and inheritance fall to ruin but he is able to retain his own self-satisfaction. The two novels hold a pessimistic view of extreme wealth and decadence, depicting patrons as vapid and unfeeling people who are prone to alcoholism. They seem to favor the idea that an examined and purposeful life full of emotional wealth is far greater and more fulfilling than materialism.

F. Scott Fitzgerald's second novel, The Beautiful and Damned, is a pseudo-allegory to his real-life struggles with his wife, Zelda. In the story, Anthony and Gloria attempt to make the most out of life and not let their best years pass them by. In doing so, they end up leading a meaningless and gaudy existence void of true happiness. When the money and youth disappear, they are left with only emptiness.

Fitzgerald's follow up, The Great Gatsby, also chronicles the death of the American Dream—this time through Jay Gatsby and Nick Carraway. Gatsby's struggles stem from the problems of society and issues with classicism's power over identity. Gatsby is left alone as well, but his situation and decline are dependent on societal habitudes and other character's decisions—both of which are out of his control. He does not succeed—though not for lack of trying.

The demise of Anthony Patch's love, health, and wealth are direct effects of his poor decisions. Gatsby grapples with an external conflict of the American Dream, while Anthony Patch's failure stems from an internal conflict.

The Beautiful and Damned was published in 1921, one year after Fitzgerald's first novel, This Side of Paradise. Fitzgerald was an overnight literary sensation with his first novel, and the second one did well but did not create the success he had hoped for. The Beautiful and Damned chronicles the married life of a young attractive couple and their lives in New York City. The couple, Anthony and Gloria, give wild parties, living beyond their means, and the marriage dissipates as financial stress and Anthony's alcoholism take their toll. The events in the novel do reflect on some level the actual marriage of Fitzgerald to his wife Zelda, and his own frustration with not making enough money (despite being very well paid as a short story writer). Fitzgerald also struggled with a drinking problem and this is portrayed in many of his stories.

The Great Gatsby's basic plot and set-up do resemble that of The Beautiful and Damned, in that there is a long time romance that is stormy, and the question of money is central. Anthony's relationship with money is one of poor decision making and lack of practicality; while Gatsby becomes obsessed with amassing wealth to impress Daisy, so that she will marry him. Anthony and Gloria's wasteful spending eventually forces them to become thrifty and change their lifestyles, but the cost is too great and Anthony becomes depressed and exhausted. Gatsby, on the other hand, builds up his wealth from humble beginnings and becomes so rich that money is no object; he spends a fortune on parties, clothes, cars, food, furnishings and decorations to impress Daisy. In both novels, the association of money with social status is paramount, and the theme of decadence among young adults in the 1920s is portrayed with detail. 

The ultimate fates of the characters are partly due to their own behavior, and partly due to the actions of others, but in both cases, wealth is a factor. Anthony's dissipation comes about because he can't figure out how to be happy unless he is rich. Gatsby's love for Daisy can't protect him when the lover of Daisy's husband is killed when Daisy is driving while intoxicated, and that woman's husband seeks revenge on Gatsby because it was his car that was identified. In this way, the fancy car Gatsby chose, to advertise his wealth and social status and to attract Daisy, led to his downfall. Both novels portray a central theme defined by the belief of various main characters that money brings happiness, and eventually demonstrating that this is simply not true.