Pursuit of an informed approach to interpreting Frédéric Chopin’s music has been increasingly challenging in the twenty-first century. In the process of forming their unique voices, pianists turn to the sound recordings of some of the most notable pianistic figures in history. This document offers a detailed inspection of three revered recordings and, with the help of syntactic analysis, seeks an understanding of the extraordinary interpretational decisions of Alfred Cortot, Arthur Rubinstein and Dinu Lipatti. The examined works are Chopin’s Prelude in C Major, Op. 28, No. 1, and the Largo of the Sonata in B Minor, Op. 58. The analysis of the Prelude compares recorded performances of Alfred Cortot (ca. 1933-1934) and Arthur Rubinstein (ca. 1946) and explains how their vastly different interpretational choices can, through an analytical process, be traced to the harmonic and melodic implications of the score. Likewise, inspection of the Largo focuses on Dinu Lipatti’s performance (ca. 1947) and draws connections between his phrasing and critical characteristics of the movement. All three performances present exquisite examples of a style of expressive playing that seems to have fallen into disuse in the twenty-first century. This study contributes to a deeper understanding of the performing style of Cortot, Rubinstein, and Lipatti, and also seeks to show connections between score analysis and interpretational decisions.