Kendrick Lamar, Pulitzer Prize-winning rapper and cultural icon, dives into his journey from the rap blog era to superstardom. He discusses the pivotal influence of Top Dog Entertainment and his groundbreaking album 'Good Kid, M.A.A.D City.' Kendrick contrasts his lyrical depth and social themes with Drake's commercial appeal, shedding light on their intense rivalry. The conversation also explores Kendrick's bold challenges in hip-hop and the cultural significance of their ongoing competition, underscoring how authenticity shapes their artistry.

Joined by Chris Ryan, a film expert, and Sean Fennessey, who knows both film and music, the discussion dives into the rich world of movie soundtracks. They kick off with a humorous toast while selecting their top picks in a live soundtrack draft, emphasizing nostalgic favorites from the 90s. The guests reflect on the cultural significance of iconic soundtracks, like those from 'Romeo and Juliet' and 'Trainspotting,' while sharing personal memories linked to these tracks. Additionally, they promote support for musicians affected by wildfires, blending humor, nostalgia, and community spirit.

This week’s guest is Leslie Gray Streeter, an author and columnist celebrated for her memoir 'Black Widow' and her novel 'Family & Other Calamities.' She joins to passionately defend Nickelback fans against the wave of anti-Nickelback memes. The duo dives into the cultural significance of the band, exploring the evolution of their image and the humorous nature of 'butt rock.' They share personal anecdotes, reflecting on the emotional depth of music and challenge listeners to embrace their musical preferences without shame.

Brittany Spano, Senior writer at Rolling Stone and adjunct instructor at NYU, shares her expertise on Rihanna's impact in pop music. The discussion dives into Rihanna's challenging upbringing and journey to fame, highlighting her reggae roots and the evolution that led to hits like 'Umbrella.' They also debate Jay-Z's guest verse, pondering its controversial status in his career. Spano and the host explore underrated tracks from Rihanna's discography and celebrate her lasting influence in shaping contemporary music.

Craig Jenkins, a music critic at New York Magazine and Vulture, joins the discussion about 311's impressive legacy. They delve into the band's unique blend of rap, reggae, and rock, highlighting their hit 'Amber.' Jenkins argues that 311 bridges musical eras, their bass work is standout, and their sound evolved from aggressive to romantic. The conversation reflects on 311's cultural impact, their innovative genres, and how they've remained relevant despite changes in the music scene.

Clover Hope, a critic and author of "The Motherload," dives into the dynamic careers of Usher and Lil Jon. The conversation highlights Usher's rise from church choir to R&B superstar, emphasizing his storytelling and emotional depth. Clover details Lil Jon's role in the crunk movement, sharing humorous anecdotes that blend wrestling matches with nightclub energy. They explore Usher's evolution across hits like "Yeah!" and "Climax," examining his impact on R&B while balancing personal narratives with commercial success.

Marissa Moss, a critic and author of "Her Country," joins the discussion on Avril Lavigne, the iconic pop star often seen as the 'anti-Britney Spears.' They explore Lavigne's influences and cultural impact, delving into the unique blend of pop and punk in her music. The conversation highlights the tensions between authenticity and commercialism in the industry, while reflecting on Lavigne's role in shaping the early 2000s music landscape. Moss also shares insights on the challenges faced by female artists and Lavigne's potential evolution into country music.

Join Brian Phillips, a senior staff writer at The Ringer and author of 'Impossible Owls,' as he dives into the emotional legacy of Johnny Cash, particularly his haunting cover of 'Hurt.' They explore Cash's evolution as an artist, his collaboration with Rick Rubin, and the poignancy of his storytelling. The discussion highlights the deeply personal nature of Cash's music, connecting themes of love, loss, and nostalgia. Phillips draws parallels between Cash's rebellious spirit and that of contemporary artists, illustrating his lasting impact on music.

John Darnielle, frontman for the Mountain Goats and an acclaimed author, joins the conversation to dive deep into Linkin Park's remarkable influence on millennial youth. They explore the emotional resonance of 'In the End,' highlighting Chester Bennington's haunting vocals. Darnielle reflects on the band's legacy in tackling mental health struggles and how their lyrical themes connected with a generation navigating adolescence. The discussion unfolds the band's evolution and lasting cultural significance, marking their irreplaceable place in music history.

Justin Charity, a senior staff writer at The Ringer known for his keen insights into music and culture, joins to talk about Missy Elliott's monumental impact on hip-hop. They delve into her legacy, focusing on the groundbreaking nature of 'Work It' and its unforgettable lyrics. The conversation celebrates Missy's resilience, unique artistry, and revolutionary music videos. Charity also elaborates on the challenges she faced alongside Timbaland, emphasizing how their partnership transformed the genre and left an indelible mark on future artists.