The Pd‐catalyzed coupling of aryl (pseudo)halides and amines is one of the most powerful approaches for the formation of C(sp2)−N bonds. The pioneering reports from Migita and subsequently Buchwald and Hartwig on the coupling of aminostannanes and aryl bromides rapidly evolved into general and practical tin‐free protocols with broad substrate scope, which led to the establishment of what is now known as the Buchwald–Hartwig amination. This Minireview summarizes the evolution of this cross‐coupling reaction over the course of the past 25 years and illustrates some of the most recent applications of this well‐established methodology. The first quarter century: The Buchwald–Hartwig amination enables the formation of C(sp2)−N bonds through the Pd‐catalyzed coupling of (hetero)aryl halides and pseudohalides with amines. This Minireview discusses the development of this methodology over the past 25 years, including highlights of some of the most recent applications.