This paper explores the development of the United States from the colonial period to the present, with a particular emphasis on its reputation as the land of opportunity and global superpower. The bright side of America based on the promises of the founding principles and basic traditional values has been the source of unsurpassed national pride and admiration by much of the world. However, the dark side of America has dimmed the beacon of democracy which has been overshadowed by instances of inequality of opportunity based on race, gender and other backgrounds, displacement, exclusion, discrimination, segregation, systemic racism, and mistreatment of its workers. The paper highlights particular events that belong to the tragic side of American history that have devalued the American creed in order to raise awareness to the fact that if America is to be truly great, it needs to rebuild its founding principles and honor its constitutional rights and responsibilities. This is illustrated in the poems “Let America be America Again” by Langston Hughes and the Inaugural Poem “The Hill We Climb” by Amanda Gorman. The selected works focus on America as a work in progress, a country that needs to rebuild and heal in order to achieve the American Dream and live up to its creed. Only then will America be a country of which its citizens can be proud and a role model for other cultures. Thus, to achieve the aspiration of a City upon a Hill, the United States needs to restore and reconstruct itself using the same founding principles to right the wrongs and eliminate anti-American sentiment.