The podcast episodes explore various topics through an intergenerational lens, highlighting the diverse perspectives and nuances that emerge when different generations engage with the same issues.

For example, the episode 'Questlove maps a cultural revolution in 'Hip-Hop is History'' delves into Questlove's role as an elder statesman of hip-hop, examining the generational divide in how the genre is perceived and understood. Similarly, 'Episode 17: Intergenerational Conversations on Organizing for Gender Equality' features a dialogue between veteran feminists and young activists, exploring the evolving perspectives on gender equality across generations.

Other episodes, such as 'S04 - Ep. 9: This Is the Weirdness' and 'Saturday Matinee: What's Ray Saying?', explore how different generations, including victims' families and medical practitioners, grapple with complex societal issues like national security and healthcare, respectively.