Connie Boswell, an influential jazz singer known for her work in the 1930s and 40s, shares insights from her storied career, including her time with the Boswell Sisters. She highlights the emotional depth in classic song lyrics, revealing how they encapsulate themes of love and nostalgia. The conversation dives into the allure and challenges of show business, emphasizing performers' resilience. Listeners also discover her soulful performances of timeless melodies from Irving Berlin and Rogers and Hart, showcasing her profound impact on jazz music.