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Obsessed: The Podcast

How I Confront MAGA's Biggest Names to Their Faces

Obsessed: The Podcast

The Daily Beast

Tv & Film

4.5686 Ratings

🗓️ 23 May 2026

⏱️ 51 minutes

🧾️ Download transcript

Summary

On this episode of Obsessed, Matt Wilstein sits down with comedy legend Robert Smigel — the creator and voice behind Triumph the Insult Comic Dog — for a hilarious and revealing conversation about his decades at Saturday Night Live, discovering Stephen Colbert and Steve Carell, working alongside Conan O'Brien and Adam Sandler, and his unforgettable experience roasting MAGA figures at the White House Correspondents’ Dinner. Smigel also opens up about the rise of Triumph, his new podcast Humor Me with Robert Smigel and Friends, and the behind-the-scenes stories from some of the most iconic moments in comedy history. Follow Kevin Fallon on Instagram ⁠@kpfallon⁠ Follow Matt Wilstein on Instagram ⁠@mattjwilstein⁠ New episodes every Thursday, and Saturday; ⁠early drops on YouTube⁠. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Transcript

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0:00.0

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Visit Medexpress.com.

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com.uk slash podcast to learn more. Attention all passengers. The Uber ride for Jeff's rugby team

0:30.2

will depart in five minutes from Platform 15. Your ride comes with six toilets and a refreshment's

0:37.1

carriage that you'll empty within five minutes.

0:40.6

Thank you for booking your tickets on Uber.

0:44.4

Trains on Uber.

0:46.0

You had mixed feelings about confronting Cheryl Hines on the carpet?

0:48.7

I just, you know, I know how much crap she's taken.

0:51.8

I always have a problem when people want to make fun of stuff that's

0:55.2

really personal. You know, I just feel like that's crossing a line to me. Well, yeah, you keep it to the

1:00.0

horrible things that they're doing for their jobs, I guess. That's your opinion. I don't know what

1:05.5

you're talking about, Matt. I did have mixed feelings about the joke. In my mind, the joke was

1:10.2

as much about her being ostracized, whether fairly or unfairly, than anything personal about her.

1:16.4

What was the joke you had prepped for her?

1:17.9

Well, I just had heard somebody interviewing her and said, what makes this night so special?

...

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