The Stonewall Riots of 1969 set the foundation for the civil rights movement of the lesbian, gay, bisexual, transgender, and queer (LGBTQ) population in the United States. Despite policies and laws, which have been enacted since that historical turning point, gay men continue to experience challenges in their lives as they emerge into their sexual identities. This chapter provides an overview and the thesis of the volume, which posits that development and negotiation of gay identity is a challenge with which many gay men grapple during their lifetimes despite the advances in LGBTQ rights over the last several decades. The thesis is explored in relation to the life narratives of three generations of gay men—the Stonewall Generation, the AIDS Generation, and the Queer Generation. These narratives are indicative of the many life challenges gay men face, the impact of these challenges on health and well-being of many gay men, but also of pride, dignity, and resilience that is evidenced in the population.