The Bill Simmons Podcast

Join Kevin Wildes, Bill Simmons's longtime friend and former ESPN colleague, and Mallory Rubin, a Contributor to The Ringer, as they dive into a hilarious discussion of half-baked ideas like basketball batting cages and indoor whitewater rafting. They also engage in a rivalry over summer foods, reminiscing about corn, ice cream, and classic ballpark hot dogs while poking fun at modern food delivery. The playful banter and lively debates make for an entertaining exploration of culinary delights and whimsical innovations.

Matthew Berry, an ESPN fantasy football expert known for his engaging insights, joins to dissect the 2019 fantasy football landscape. They delve into high-stakes leagues, drafting strategies, and analyze key players like Alvin Kamara and Saquon Barkley. The conversation also touches on the quarterback dilemma, the excitement of auction drafts, and the evolving nature of fantasy sports. Additionally, they share humorous nostalgia while reflecting on the recent '90210' reboot, combining insights on football with lighthearted banter about TV classics.

Brian Windhorst, an ESPN reporter celebrated for his insights into LeBron James and the NBA, shares his experiences with Team USA and standout talents like Jayson Tatum and Donovan Mitchell. The conversation dives into the playoff prospects for the Utah Jazz and the fiery rivalry between the Lakers and Clippers. Windhorst also predicts the upcoming season for LeBron and discusses evolving player dynamics and the impact of social media in the NBA landscape.

Wesley Morris, a Pulitzer Prize-winning critic for The New York Times, joins the conversation to dissect Quentin Tarantino's 'Once Upon a Time ... in Hollywood.' They explore Brad Pitt's star power and how his performance marks a turning point in his career. Morris highlights Margot Robbie's portrayal of Sharon Tate, showcasing her innocence in a tumultuous era. The duo also delves into the film's nostalgic recreation of 1960s Hollywood, tackling themes of masculinity and societal critiques that lie beneath the surface.

Sarah Silverman, a powerful voice in comedy and actress known for her sharp wit, joins to share insights on the evolving landscape of stand-up and television. They dive into the challenges of cancel culture, the typecasting of women in Hollywood, and the importance of artistic risk-taking. Silverman humorously connects comedy with her love for basketball, reflecting on live performances and personal anecdotes. The conversation also tackles media representation, social media engagement, and the absurdities of public discourse, providing a candid look into her creative journey.

Ryen Russillo, a seasoned sports radio host now at The Ringer, joins the conversation to tackle fascinating topics. They dive into Tom Brady’s aging career and his relationship with the Patriots. The discussion shifts to Ezekiel Elliott's potential holdout and the financial complexities of NFL contracts versus their NBA counterparts. Insightful thoughts on LeBron James’s influence in the NBA and the evolving dynamics between players and fans are also shared. Plus, they tease exciting collaborations on the horizon!

Kara Swisher, a prominent tech journalist, joins for a captivating discussion on the evolution of technology and social media. She reflects on her early internet experiences and the impact of major tech companies, like Facebook, on society. The conversation dives into the cultural influence of science fiction on tech, while also questioning accountability in leadership. They tackle Disney’s content dominance and its effects on innovation. Swisher emphasizes the need for ethical standards as technology continues to evolve, providing her insights on future industry challenges.

Chuck Klosterman, a prominent author known for his fresh takes on pop culture, shares insights on navigating book tours in the age of selfies and social media. He discusses the complex intersections of sports and politics at ESPN, particularly through LeBron James’s public parenting. The conversation dives into the cultural legacy of figures like Charles Manson, while reflecting on music evolution from classic rock to modern influences. Klosterman also contemplates the societal ramifications of UFOs and the ideal presidential candidate, making for an engaging blend of humor and thought.

In this engaging discussion, JackO—a seasoned sports commentator—delves into the heated Yankees-Red Sox rivalry and the nuances of MLB trade deadlines. He also humorously critiques the chaotic Democratic primary landscape. Joining him, Michael Rubin, the savvy owner of Fanatics and part-owner of the Philadelphia 76ers, shares insights into sports team ownership and the evolving world of sports merchandise, including real-time production and combating counterfeit goods. Together, they navigate the intersections of sports, politics, and media.

Actor Kevin Costner, known for his iconic roles in films like Dances with Wolves and Field of Dreams, shares behind-the-scenes insights from his Hollywood career. He reflects on the challenges of filmmaking, casting stories from Bull Durham, and the delicate balance between creative integrity and financial pressures. Costner also dives into the emotional connection baseball movies have with audiences, celebrating Field of Dreams' lasting impact. Alongside this, discussions touch on navigating fame's pressures and the importance of self-confidence in acting.