John Heilemann welcomes The Daily Show's Jordan Klepper on the eve of his new election special, Jordan Klepper Fingers the Midterms -- America Unfollows Democracy, which premieres on November 1, and on the heels of of his turn as a guest host on Heilemann's Showtime series The Circus. Heilemann and Klepper dig into the all-important Pennsylvania Senate race and the eagerly awaited, much-discussed debate last week between John Fetterman and Dr. Oz; Klepper's comedy heroes, from British icons such as Monty Python, Chris Morris, and Steve Coogan to his Daily Show forerunners Jon Stewart, John Oliver, and Samantha Bee; his career on The Daily Show, including his trademark interviews with MAGA voters at Trump rallies; his new special, and how the election denialism he encountered in places such as Michigan and Arizona fed his fear that the midterms could be the beginning of the end for American democracy. Klepper also explains why he sees Bob Dylan (yes, Bob Dylan) as a comic genius— and the first verse of his song Highway 61 Revisited as the greatest joke in the history of rock lyricism.
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Jordan Klepper

Living in America these past few years has been like living in a movie—a mashup of Blade Runner, A Clockwork Orange, and Idiocracy, that is. The never-ending pandemic, the routine mass shootings, the climate literally and figuratively on fire; the economy first battered by recession, then ravaged by inflation; an angry electorate, armed to the teeth and addled by conspiracy theories, as our democracy teeters on the brink, with Donald Trump still working overtime to push the whole thing off a cliff. On Hell and High Water, John Heilemann — host of Showtime's The Circus, co-author of Game Change, and national affairs analyst for MSNBC — explores this apocalyptic-seeming moment with seminal figures in politics, entertainment, business, tech, the media, and beyond. The conversations are deep, rich, and bracingly real, but also hopeful, as Heilemann and his guests grapple with the fact that, to quote Bob Dylan, “Everything is broken,” and try to figure out how to fix it … together.


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In which John Heilemann talks with Cecile Richards, co-chair of the Democratic super PAC American Bridge 21st Century, co-founder of the women’s rights advocacy group Supermajority, and, from 2006 to 2018, president of Planned Parenthood Federation of America. Heilemann and Richards discuss Roe v Wade's uncertain future in the wake of the recent Supreme Court arguments around restrictive abortion laws in Mississippi and Texas, and the effects that Roe's potential demise might have on women and politics in America; how Richards's mother, Ann, the former governor of Texas, propelled her towards a lifetime of activism; and how her broader agenda in favor of "women's equity" is faring in the Biden era.
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Cecile Richards

A special two-part episode in which John Heilemann talks with international affairs and national security guru Tom Nichols, contributing writer at The Atlantic, longtime senior faculty member at the U.S. Naval War College, and author of eight books on foreign policy and politics, including, most recently, Our Own Worst Enemy: The Assault from Within on Modern Democracy. Heilemann and Nichols assess the state of the Russian invasion of Ukraine, Vladimir Putin’s calculations in the face of the Russian military's inability to win a swift and decisive victory, and the emerging consensus in the West that war has reached what could prove to be a protracted and bloody stalemate; how President Zelenskyy has wielded a masterful media strategy to galvanize support around the world and dominate the information battlefield; and the difficult decisions facing Joe Biden and the NATO alliance as Zelenskyy warns that we may already have entered World War III. Nichols also discusses his proud status as a five-time, undefeated Jeopardy champion, and his well-known – and well-deserved – reputation for having indefensibly and inexplicably bad taste in music.
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Tom Nichols Part 2

Tom Nichols Part 1

Shannon Watts is the founder of Moms Demand Action For Gun Sense in America — a self-described “accidental activist” who, in less than a decade, went from being a stay-at-home mother in Indiana to the face of a national grassroots movement with more active members than the National Rifle Association. When Watts launched her advocacy group as a simple Facebook page in the wake of the Sandy Hook school shooting in December 2012, she had just 75 friends on the site but grand ambitions, boundless energy, and infinite chutzpah. Today, Moms Demand Action is part of Everytown For Gun Safety and a political juggernaut, deploying tens of thousands of volunteers and tens of millions of dollars to support candidates, legislative campaigns, and corporate reform efforts. Heilemann and Watts discuss the ways her group has changed the game on gun control, the role of women and young people in the movement, the crisis at the NRA, and why Watts believes the Biden administration will be “the strongest gun safety administration in history.”


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Shannon Watts

Kurt Andersen and Lawrence O’Donnell first met 46 years ago as undergraduates at Harvard, forming a friendship that’s flourished alongside their careers as two of their generation’s most incisive, insightful observers of American politics and culture. Andersen made his mark in the 1980s as co-founder of the iconic Spy magazine, then went on to serve as editor-in-chief of New York magazine, host of the Peabody Award-winning radio program “Studio 360,” and best-selling novelist and non-fiction author. O’Donnell cut his teeth in Washington as staff director of the powerful Senate Finance Committee and protege to legendary New York Senator Daniel Patrick Moynihan, then transitioned to the TV business — first as an Emmy Award-winning writer on “The West Wing” and currently as host of “The Last Word” on MSNBC. On this week’s Hell & High Water, Heilemann, a friend of both Andersen and O’Donnell, brings the two men together for their first-ever joint interview. They discuss the performances of Joe Biden and Amanda Gorman on inauguration day, O’Donnell’s insider’s perspective on the January 6 assault on the US Capitol, and Andersen’s “grand unified theory” of modern American life, as sketched out in his recent companion volumes, “Fantasyland” and “Evil Geniuses.”
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Jordan Klepper

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