Second Thought

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Jeff Ross on Tom Brady, Trump, and the Roast of Kevin Hart

June 12, 2026

Roast comedy is one of the last places where truly unfiltered commentary still lands in public, says “Roastmaster General” Jeff Ross. Few people understand the art of the insult better than Ross, who has presided over the brutal, hilarious takedowns of everyone from Joan Rivers and Justin Bieber to Charlie Sheen. Today, he joins Suzy Weiss to break down his new Netflix special, Take a Banana for the Ride, which manages to be both hilarious and serious—addressing the loss of both of his paren...

I Am Not a Robot (but My Boyfriend Was)

June 05, 2026

For a year, tech writer Joanna Stern turned herself into an AI guinea pig. She let artificial intelligence into every corner of her life: testing robot assistants, commuting in autonomous vehicles, reading AI bedtime stories to her children, and even going on a road trip with her AI boyfriend, Evan.  That experiment became her new book, I Am Not a Robot. In this episode, Joanna breaks down what we can expect from the next wave of AI technology. One question hangs over the episode: When the p...

Scooter Braun on Taylor Swift, Kanye West, and Becoming the Internet’s Villain

May 28, 2026

Scooter Braun reflects on how he became one of pop music’s most powerful kingmakers, helping to engineer the careers of Justin Bieber and Ariana Grande—and the controversies that reshaped his public image, from Kanye West’s antisemitic spiral, which ended their relationship, to the Taylor Swift masters dispute that turned Braun into one of the internet’s biggest villains. Braun says he barely knew Swift personally and argues the feud was flattened into a simplified tale that painted him as a...