This chapter focuses on the representation of bridges in literature, movies and painting about and by Italian Americans. While the bridge has been described both as a place in which cultures and social classes can meet, many of the text, films and artworks analyzed in this chapter show that this architectural element is often represented as a border between different social, economic, and ethnic groups. The analysis highlights a shift between the use of the bridge to emphasize the discrimination of Italian Americans in a society dominated by the white American Protestant elite towards the beginning of the 20th century to the use of this architectural element to emphasize a difference in terms of class and race privilege between Italian American and non-white ethnic groups towards the end of the century. The article ultimately proposes to avoid using the trope of the “bridge between cultures”, since it implies that cultures are separated and do not continuously hybridize each other.