Bill Maher and Two and a Half Men star Jon Cryer on border policies and media coverage, on how progressive issues influence elections, youth gender-affirming care, and social media “contagion” vs. authentic identity, how Jon grew up in a rough part of the Upper West Side, crime stories and colorful neighbors in 1970s–80s NYC, Jon’s acting journey, the podcast Jon produced, The Man Who Calculated Death, Jon’s on set experience with Charlie Sheen and how the show changed when Charlie relapsed, Elon Musk’s contributions to electric vehicles and space exploration vs. controversies regarding Twitter/X and political stances and much more!

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