Is the American Dream real and achievable? To what degree/extent? How can I use these sources to make an argument? The sources are: Wilson - Fences (the movie); Fitzgerald - The Great Gatsby; Roosevelt - Fireside Chats; Rawlings - The Hard Path to Citizenship; Ehrenreich - Since When is it a Crime to be Poor; other relevant materials

This is a fairly complex assignment. In your first paragraph, you should set out a discussion of what your paper will be addressing. Perhaps the best issue to talk about is the decline in social mobility and increase in income inequality of the past few decades. Once you make a basic statement that the "American Dream" is less possible for many Americans due to these changes, you should set out what you intend to discuss in the following sections. Issues you might address are:
Definition of American Dream:The phrase was first defined by 1931. Historian James Truslow Adams in his book 1931 volume Epic of America. in the following passage: "The American Dream is that dream of a land in which life should be better and richer and fuller for everyone, with opportunity for each according to ability or achievement." After this definition, you might talk about how these ideals existed before the phrase itself and how they are embodied in the Declaration of Independence and Constitution. You can then trace the degree to which these ideals compare with the historical changes in social inequality and social mobility.
Gatsby: The first main body section of your essay should discuss Gatsby and his self-invention as an embodiment of the American Dream, both its successes (Gatsby does get rich) and failures (he is a criminal; he is not accepted by upper class society). You might look at this in light of the "robber barons" and the brief period of massive creation of wealth and the subsequent collapse into the Great Depression.
President Franklin D. Roosevelt: In his Fireside Chats, Roosevelt was concerned with offering Americans a "New Deal" that promised economic opportunity and home ownership on a wide scale, creating vast public works projects and widespread economic security.
The Hard Path to Citizenship: The United States was originally a country of immigrants who arrived believing in a promise of economic opportunity in a vibrant New World. Rawls argues that immigrants now face a harder path, although the Obama administration had taken steps to ensure that a path to the American Dream would be accessible to "Dreamers," an effort that may well be rolled back by his successor.
Since When is it a Crime to be Poor: In this essay, Ehrenreich argues that our legal system almost seems designed to keep poor people in poverty.
Conclusion: Your conclusion should discuss how this history of the American Dream shows a difference between our ideals and the reality of growing inequality and lack of social mobility.
https://www.theatlantic.com/business/archive/2015/07/america-social-mobility-parents-income/399311/