• Late night legend Craig Kilborn: 'I guess podcast is king'
    Mar 25 2026

    This week, S.E. continues her streak of broadcast-legend guests (see: Sally Jessy Raphael, Ricky Lake, Josh Mankiewicz, Andy Cohen, & more!) with Craig Kilborn! Craig talks about being the original Daily Show host, his dream-job late night spot, and how, after a career getting to do a little bit of everything, Craig is finally doing something he's really pinned for — and he breaks that news right here on Off the Cupp!

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    1 hr and 5 mins
  • Talkin' Politics: Forget Democracy, we need the government to function first
    Mar 21 2026

    On this week's Talkin' Politics, S.E. wonders, what is Tulsi Gabbard's end game? The Director of National Intelligence embarrassed herself during a hearing on the Hill this week defending Trump's decision to go to war with Iran and that's after spending her political career fighting the very existence of endless wars. Confusing! But also, did you know there's STILL a government shutdown going on? If you've traveled lately, you've probably felt the sting. If you haven't yet, just you wait because if Congress can't right this ship, airports are going to shut down just in time for spring break. What a thrill to be an American! S.E. gets into all of it with her CNN colleague and host of the TrailBlaze podcast, Jamal Simmons.

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    40 mins
  • Barstool Sports’ Kevin Clancy’s advice? Don’t start a podcast
    Mar 18 2026

    This week, S.E. chats with Barstool Sports’ Kevin Clancy (KFC) about social media, his decision to end his popular podcast, and how he navigates internet fame, virality (not the good kind), and staying authentic. They talk controversies, share strong opinions, and offer advice for aspiring content creators (advice that S.E. isn’t taking personally). And stay tuned for a very fresh lightning round and everybody’s favorite subject … pizza.

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    1 hr and 1 min
  • S.E.’s Talkin’ Coffee … and RFK Jr. better listen!
    Mar 16 2026

    S.E. is back with her producers Lauren and Derrick to discuss all the news that's fit to sip, including an alarming attack by the United States Secretary of Health and Human Services on S.E. spiritual home, Dunkin’ Donuts. Plus, Lauren reports on the “damn fine cups of coffee” she had on a recent visit to a Twin Peaks gathering.

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    37 mins
  • Talkin' Politics: Bombs and bombast
    Mar 14 2026

    This week on Talkin’ Politics, S.E. lays out the many baffling statements President Trump has made regarding the war in Iran, its progress, and its objectives. He doesn’t sound like a president talking about war. Then, S.E. dives further into the week’s news with former Pennsylvania representative Charlie Dent.

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    33 mins
  • Everybody loves Phil Rosenthal
    Mar 11 2026

    Oh this is fun! This week, S.E. gets to spend an hour with the hilarious and delightful Phil Rosenthal, TV writer, producer and host, best known for the long-running sitcom Everybody Loves Raymond and his Netflix food/travel series, Somebody Feed Phil. S.E. and Phil get into his early acting desires, how 'Raymond' came to be, and how he manages the rejection inherent in the business (not to mention the business's rocky evolution). He shares some of the real-life stories that made his beloved sitcom so relatable and talks about his love of diners (and why he recently opened his own.). Also, Phil and his daughter, Lily, just released their second children's book, Just Try It! Someplace New (available now), a picture book about anxiety and change.

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    57 mins
  • Talkin' Politics: Texas, Iran & Noem, oh my! [w. Adam Kinzinger]
    Mar 7 2026

    It has been a week (de ja vu) and S.E. attempts to tackle it all on this week's episode of Talkin' Politics. Where to begin. There's the Texas primaries and what the results mean for the midterms. There's the war with Iran that we are now engaged in. And the week capped off with the Department of Homeland Security Secretary, Kristi Noem getting unceremoniously fired. And S.E. gets into all of it with her friend and former Congressman Adam Kinzinger. Buckle up!

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    33 mins
  • The perfect storm of midlife
    Mar 4 2026

    If you're a close listener of Off the Cupp, you will have picked up on one of the themes running through a lot of S.E.'s conversations — midlife. S.E. has talked with guests from Wings' Steven Weber to comedian Sherri Shepherd, to The West Wing's Janel Maloney about this moment in life where you start to take stock of your life and career, often fighting or leaning into this feeling of upheaval. But why is this period so tumultuous and how can we make it work for us? On this episode of Off the Cupp, S.E. dives into these questions with someone exploring them and this topic deeply. Author and journalist Stacey Lindsay shares the insights she learned writing her forthcoming book, Being 40: The Decade of Letting Go — and Embracing Who We Are (pre-order now). There's lots to learn about the emotional, physical, and sometimes existential tenor of this decade — whether you’re past it, in it, or looking down the 40s pipeline.

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    48 mins