Questlove, renowned musician and cultural commentator, chats with Trevor about essential topics like the recent Grammy celebration marking 50 years of hip-hop and insights from his book, Hip Hop is History. They delve into the logistical juggernaut behind the Grammy performance and share personal anecdotes, including the wild dynamics of his legendary game nights. Questlove also reflects on the evolution of hip-hop, the intertwining of personal and societal issues, and the emotional power of music, revealing the joy found in connection and storytelling.