This paper provides a thorough analysis of U.S. Congressional history from the 66th to the 118th Congress, examining demographic trends, political shifts, and party dynamics across decades. Using Python-based data processing, the study compiles and interprets historical data to identify patterns in representative demographics, party representation, and legislative impact. The analysis investigates generational changes within Congress, with a particular focus on age distribution, tenure, and shifts in political party dominance. Visualizations and statistical insights generated through Python libraries, such as Pandas, Matplotlib, and Seaborn, reveal significant historical events and socio-political influences shaping Congress. By examining age-related trends, the study highlights a generational gap, with older members retaining significant representation and a younger cohort gradually emerging. Additionally, it explores the evolution of bipartisan dominance and third-party representation, offering insights into political diversity and the resilience of the two-party system. This research contributes to the understanding of how demographic and political transformations within Congress reflect broader societal trends and may influence future governance.