Dr. Gerling (AKA Arrogant Leader on RG) compiled this list of songs for an English course focused around the idea of the American dream. See his original assignment on Rap Genius.
Suli Breaks, "American't Dream" (spoken word)
James Brown, "Livin' in America"
Leonard Bernstein & Stephen Sondheim, "America" (from *West Side Story*)
David Byrne, "Miss America"
Neil Diamond, "America"
GOG, "Brasil com 'P'"
Gogol Bordello, "Immigraniada"
Lee Greenwood, "God Bless the U.S.A."
Faith Hill, "American Heart"
John Cougar Mellencamp, "Pink Houses"
Dave Matthews, "American Baby"
Brad Paisley, "American Saturday Night"
The Pogues, "Thousands Are Sailing"
Rise Against, "Satellite"
Hank Williams, "American Dream"