The podcast episodes explore the challenges and significance of portraying iconic roles, delving into the acting process, the weight of honoring previous interpretations, and the ability to make the characters their own.

For example, the episode 'CABARET (Eddie Redmayne & Gayle Rankin)' discusses the experiences of the stars of the Broadway revival of Cabaret, and how they navigated the iconic Emcee and Sally Bowles roles. Similarly, the episode 'QLS Classic: Anika Noni Rose' features insights from the actress who voiced the iconic Disney character, Tiana, in 'The Princess and the Frog'.

The episode 'Danielle Brooks' also explores the legacy of the iconic Sophia role from 'The Color Purple', as the actor discusses inheriting the part from Oprah Winfrey's portrayal in the original film.