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The Problem With Jon Stewart

Tv-and-film • Comedy • Society-and-culture

The issues we tackle on The Problem With Jon Stewart are Too Big for TV™—so they spill over into the brilliantly titled The Problem With Jon Stewart podcast. Jon is joined by the staff and expert guests for nuanced discussions, updates on action items, and airing of grievances from writers overRead more

Popular episodes

Jon Talks to Mark Cuban: Billionaires, Basketball, and Bitcoin

Jan 13 • 46:50

We’re back, baby! We’re kicking off 2022 with billionaire/colonoscopy bargain hunter Mark Cuban. Jon and Mark discuss the American Dream, barriers to entry, and why tying healthcare to jobs makes no sense. And what’s a chat with a tech billionaire if crypto doesn’t come up? Jon is joined by show writers Tocarra Mallard and Rob Christensen to talk national anthems and Jon’s...

The Problem With Jon: According to Our Listeners

Dec 9 • 45:53

We finally checked our voicemail and hereby present our first ever mailbag episode. Jon is joined by Chelsea, Jay, and Robby to engage with your questions, comments, and criticism about the show and Jon’s increasingly fragile appearance....

Jon Talks With Steve Kerr: The Nicest, Whitest Man in Basketball

Dec 2 • 49:46

Steve Kerr thinks he’s here to talk with Jon about his career, speaking out on social issues, and the racial and political dynamics of the NBA. And he does get to talk about those things, but not before enduring Jon’s pleas for him to coach the Knicks. Staff writers Jay and Henrik offer some color commentary as well. ...

The Problem With Guns (and Domestic Abusers)

Nov 18 • 37:38

Domestic violence is a predictor for gun violence, yet we have a problem enforcing laws that strip firearms from domestic abusers. Jon talks with head writer Chelsea Devantez about her experiences with these issues, possible solutions...and also, somehow, puppet TV shows from the '70s. Jon then talks with bounce musician Big Freedia about her documentary, Freedia Got a Gun...

The Problem With War: Veterans Day Episode

Nov 11 • 52:26

It’s Veterans Day, so we're talking to some vets. Jon is joined by Staff Sergeant Wesley Black, who sadly passed away shortly after this episode was recorded, and Sergeant Isiah James. You may remember them from the Apple TV+ episode we did on burn pits—if you didn’t see it, you really should. Jon also catches up with his friend, Air Force Senior Master Sergeant Israel Del...

The Problem With the NFL: Keyshawn Johnson Explains

Nov 4 • 35:31

Fantasy football legend Jon Stewart sits down with real football legend Keyshawn Johnson to discuss coach Jon Gruden’s leaked racist emails and how the power structure of the NFL enables such behavior. Jon is also joined by Kris Acimovic and Kasaun Wilson, who don’t hold back on the Gruden controversy....

The Problem With Our Not-At-All-Free Market

Oct 28 • 41:47

In this episode, Jon sits down with Claudia Sahm, a former Federal Reserve economist with a passion for dunking on Larry Summers. They discuss the American economic system, who gets that sweet government cheese, and why Jon wasn’t as wrong as Jamie Dimon insisted....

Jon Talks With Jamie Dimon, CEO of JPMorgan Chase

Oct 21 • 58:53

In the United States, we pride ourselves on having a free market economy—but we don’t actually have one. Corporations are given endless help while workers often struggle to survive. Jon sits down with Jamie Dimon, CEO of JPMorgan Chase, to discuss these two sides of the economy....

The Problem With Freedom: It Ain’t Free

Oct 14 • 01:02:33

We’re talking freedom and race in America (we know!). Jon, who is famously old and white, is joined by staff writer Kasuan Wilson and associate producer Trey Sherman before talking to Alex Stamos, former chief of security at Facebook and current director of the Stanford Internet Observatory, about the impact of social platforms on democracy—and guess what? It’s not great....

The Problem With War: You Break It You Buy It

Oct 7 • 43:15

Like the annoying guy at a party who won’t shut up about Bitcoin, we have some investment advice: America is not investing enough in our veterans, both emotionally and financially. So today, Jon sits down with some staff who are very emotionally invested, and also talks to Professor Linda Bilmes about her proposed solution for investing more financially....

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