This paper intends to explore the precarious masculinity in the celebrated sitcom Friends by considering it alongside the urbanization in the United States in the 1990s, which was overlapped with the development of post-feminism, neoliberalism, and the third industry. This paper intends to show that masculinity in Friends is demonstrated as precarious and instable, whose preservation relies on the repetition of certain gendered rituals, acts and ornamentations. This is because body politics, shaped by discourses about urban masculinity operates in a subtle way in Friends, governing and regulating the male characters, which leads to their self-scrutiny against homosexuality and femininity. A celebrated cultural icon, Friends continues to attract audiences around the world and its popularity can be taken as a projection of the nostalgia/expectations of a prosperous era. However, it is important to understand that Friends should be viewed as representations of a certain era, instead of an icon of universal values and expectations of lifestyles, because values regarding gender, race, and identity are no longer appropriate today and neoliberal boom which provided the context for Friends has already suffered from a bankruptcy.