Lydia Polgreen, a New York Times opinion columnist; Maura Johnston, a Boston music critic; and Estelle Caswell, a former Vox journalist, dive into the enduring impact of Tracy Chapman's debut album. They explore why its messages of social justice resonate with Gen Z today. The conversation also highlights the significance of music covers and the role of Black artists in country music, alongside reflections on poetic themes present in Chapman's work. The guests celebrate women in music through Joni Mitchell’s Grammy comeback and discuss the cultural relevance of Gen X artists.

Guest Maura Johnston discusses Britney Spears' impact on pop music, highlighting her voice and sound that ushered in a new era. They explore Britney's use of wordless vocalization, embrace of technology, and rejection of 90s grunge rock. The podcast also discusses Britney's album Blackout, her personal struggles, and her cultural significance. They explore the brilliance of her hit song 'Oops, I Did It Again', emphasizing its lasting influence on pop music.