This dissertation examines whether place matters for Americans’ pessimism about the American Dream and if so, how place matters. First, I establish that place (conceptualized in terms of region and size of place) influences individual-level pessimism about the American Dream. Pessimism about the American Dream is measured with a General Social Survey (GSS) question on chances of improving one’s standard of living. I then use GSS data to analyze whether individual-level characteristics (race, sex, age, income, unemployment, educational attainment, marital status, and homeownership) help explain the influence of place on pessimism about the American Dream when respondents are nested in their county of residence; in other words, whether place matters because different places have different compositions of people. Next, I use GSS data merged with IPUMS USA (IPUMS) data to analyze whether county-level characteristics (race, sex, age, income, unemployment, educational attainment, marital status, and homeownership) help explain the influence of place on pessimism about the American Dream when respondents are nested in their county of residence; in other words, whether place matters because different places have different contexts. Finally, using the merged data, I analyze the interactions of the individual-level and county-level characteristics when respondents are nested in their county of residence; in other words, whether place matters differently for different people. While I am not able to quantify how much composition and/or context explain the influence of place on pessimism about the American Dream, I find that that different compositions of people in different places contributes to the influence of living in the Midwest compared to the Northeast. I also find that different age contexts in different places contribute to the influence of living in the Midwest compared to the Northeast, the influence of living in the West compared to the Northeast, and the influence of size of place (living in a suburban, exurban, micropolitan, and/or rural area compared to an urban area). County-level age is the only statistically significant county-level characteristic. My findings suggest that living in a county with a higher mean age is associated with increased odds of pessimism about the American Dream compared to living in a county with a lower mean age. I do not find any statistically significant interactions between the individual-level variables and the county-level variables. Throughout my dissertation, the influence of living in the South compared to the Northeast consistently remains statistically significant. I find that living in the South is associated with decreased odds of pessimism about the American Dream compared to living in the Northeast and that composition and context do not explain the influence of living in the South on pessimism about the America Dream. My findings suggest that the influence of living in the South on pessimism about the American Dream may be due to collective explanations, such as shared norms and values in the region. / Sociology