Fractures of the proximal femur, particularly intertrochanteric and subtrochanteric fractures, remain a major orthopaedic challenge due to their high incidence in the elderly, complex biomechanics, and frequent association with osteoporosis. Management of these injuries has evolved significantly over the past century, shifting from conservative treatment and rigid extramedullary constructs toward biologically favorable, load-sharing intramedullary systems that facilitate early mobilization and functional recovery. Early fixation methods, including angled blade plates and the Dynamic Hip Screw (DHS), were effective in stable intertrochanteric fractures but demonstrated limitations in unstable patterns, especially those with medial calcar deficiency, lateral wall compromise, or subtrochanteric extension, often leading to varus collapse, screw cut-out, and mechanical failure. These shortcomings drove the development of cephalomedullary nails in the 1990s, beginning with the Proximal Femoral Nail (PFN) and subsequently refined through PFNA, PFNA2, Gamma3, InterTAN, TFNA, and emerging designs such as the Proximal Femoral Bionic Nail (PFBN). Contemporary evidence supports the use of cephalomedullary nails as the preferred fixation for unstable intertrochanteric (AO/OTA 31-A2/A3) and subtrochanteric fractures due to their central load-sharing position, shorter lever arm, and superior resistance to varus and torsional forces. Nonetheless, complications such as implant fatigue, nail breakage, and peri-implant fractures have been reported. DHS remains a reliable, low-cost option for carefully selected stable intertrochanteric fractures with intact medial calcar and lateral wall. This narrative review synthesizes the historical, biomechanical, and clinical evolution of fixation strategies for peritrochanteric femur fractures and emphasizes that optimal outcomes depend on appropriate implant selection, fracture morphology, bone quality, and meticulous surgical technique.