Jon Lovett takes extreme Offline challenge in Fiji, Surgeon General's warning label for social media proposed by Vivek Murthy, Brian M discusses AI development slowdown and workers organizing against tech. Topics include AI progress plateau, AI monitoring in workplace, effects of automation on skilled workers, challenges of AI integration, and ethical implications in the tech industry.

Oprah Winfrey, the legendary media mogul and philanthropy icon, joins the discussion with North Carolina's controversial Lieutenant Governor Mark Robinson, who is scrutinized for his provocative online presence. The conversation highlights Kamala Harris's slight polling edge and upcoming reproductive rights event featuring Oprah. Jon Lovett shares insights on his brief stint on Survivor, blending humor with reflections on strategy and alliances. Together, they explore the political landscape, campaign dynamics, and the impact of social controversies on voter sentiment.

Jon Lovett, a political commentator, joins notable author J.D. Vance to navigate the controversial waters of Project 2025. They humorously unpack its implications on women's rights and societal changes. Olivia Warren and Deeva Shah delve into serious judicial misconduct, exposing the troubling case against Judge Joshua Kindred and the systemic challenges in addressing harassment. The discussion highlights the need for accountability in the judiciary while reflecting on the broader political landscape and upcoming reforms.

Jon Lovett, a reality TV persona, joins the hosts to discuss Trump's probation meeting, Biden's campaign strategies, and a quiz about the news he missed. They also cover Trump's tax cuts plan, challenges faced by incumbents, and controversies surrounding political appointments and legal troubles.

Jon Lovett, co-founder of Crooked Media and former Obama aide, shares insights on successfully navigating the turbulent political media landscape since the 2016 election. He discusses the challenges of engaging with an increasingly divided electorate, especially amid the Trump era. Lovett reflects on the uninspiring election season, the personal impacts of a digital detox, and the humor found in political commentary. He also weighs in on Biden's debate performance and the concerns surrounding his age, adding a light-hearted touch with tales from reality TV.

Podcaster and political savant Jon Lovett of Crooked Media fame joins Kara Swisher to discuss the podcast biz, unions, and Trump and Biden's chances in '24. They also delve into the crisis within the GOP, challenges of monetizing a podcast, and the upcoming presidential contest.

Political commentator and former Obama speechwriter Jon Lovett joins Tim Miller to discuss the possible options as the world waits for Biden to make a move. They analyze Biden's debate performance, contemplate his potential resignation for Kamala Harris, and examine the impact of local elections on community engagement.

Jon Lovett, former Obama speechwriter and co-founder of Crooked Media, discusses Biden's accomplishments and media coverage. He highlights the lack of awareness among voters and the importance of effective communication. Lovett contrasts Biden's performance with Trump's energy and mental state. The podcast also delves into the challenges of conveying political achievements amidst media scrutiny and the need for improved communication strategies.

Jon Lovett, co-founder of Crooked Media and host of "Lovett or Leave It," engages in a thought-provoking discussion with Tim Miller. They tackle how the worst people feel validated in their beliefs while the best are filled with uncertainty. Lovett shares insights on the alarming normalization of Trump's practices, particularly regarding immigration policy. They explore the emotional toll of political disillusionment and emphasize the importance of resilience in facing a tumultuous climate. Laughter and reflection flow as they navigate the complex landscape of contemporary American society.

Crooked Executive Producer Kendra James and Jon Lovett discuss 'You've Got Mail' and its portrayal of '90s internet culture, including the shift from traditional mail to email, the impact of the internet on personal lives, and the dual identities maintained online. They also explore the nostalgia of AOL, online dating stigma, and the economy of the era.