Jessica Simpson, a pop star turned fashion mogul and author, joins culture writer Lindsay Mannering for a fascinating conversation. They explore Simpson's evolution from reality TV icon to business powerhouse, sharing favorite moments from 'Newlyweds.' The discussion highlights her struggles with body image and addiction, showcasing her resilience. They also touch upon the media's portrayal of female celebrities and the importance of storytelling. Lastly, they reflect on the enduring appeal of Simpson's brand and her impact on contemporary culture.

A deep dive into Jessica Simpson's journey from pop star to fashion mogul, discussing her enduring staying power, favorite moments from 'Newlyweds', media portrayal of female stars, and speculation about a pop star comeback. The episode also includes insights from meeting Jessica at her home and explores her multifaceted success story in the industry.