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IMO with Michelle Obama and Craig Robinson

Get a Hobby, Be Happy with Jessica Williams

IMO with Michelle Obama and Craig Robinson

Higher Ground

Society & Culture, Self-improvement, Education

4.313.8K Ratings

🗓️ 10 June 2026

⏱️ 69 minutes

🧾️ Download transcript

Summary

On this episode of IMO, actress, host, and podcast veteran Jessica Williams joins the show! She discusses what it was like to have Jon Stewart as a mentor during her early tenure at The Daily Show, how she has had to approach her acting career as a tall Black woman in Hollywood, and the surprising crafting projects she’s picked up in her down time. Plus, Jessica shares her favorite stories from behind the scenes of Shrinking.

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Transcript

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0:00.0

I'm doing a rom-com right now that I think you'll be really excited about.

0:03.2

It's like me and a shorter, a guy who's shorter than me.

0:05.9

I love you.

0:06.5

And I'm really excited. And I was like trying to tell him, I was like, look at Tom and Zendaya. And he's like, no, I'm not going to Google that. But I know for me, it's my info is Tom and Zendaya. And I love looking at foot. I love looking at them walking around in London with their little dog,

0:21.4

and he's a little short king, and she's a tall queen, and it just looks so right.

0:25.1

It just looks so right.

0:26.3

And it's like, why, Hollywood?

0:28.1

Why?

0:28.6

It looks good.

0:29.5

We can do this.

0:30.0

We can do this.

0:36.7

This episode of IMO is brought to you by Progressive Insurance.

0:42.2

Howdy.

0:43.2

Craig Robinson.

0:45.1

This is very comfortable. It looks like a pajama top.

0:48.2

Well, that's what it's supposed to. It's fashion, as I say.

0:52.2

Really?

0:52.8

There's the look. It's the pajama. No wonder kids are wearing pajamas to school. Who's giggling about pajamas? It's like. Crystal, it looks like a pajama top and she said. Well, what's so funny? I'm just making an observation. It's just you not knowing things about the world and fashion. I didn't know that you could wear a pajama's top. It's not a pajama's top. It just looks like it mimics a pajama. It mimics sort of the comfortable.

1:19.1

But if it actually looks like a pajama top, why couldn't you wear a pajama top?

1:24.8

There's, you could. And some people do actually wear the pajama top as fashion.

1:30.5

This just happens to be a blouse that is fashioned after pajamas. And there's also, now, I don't know whether this had bottoms, but a look would be this exact same bottom, matching the bottom.

1:43.5

Right. Have you seen people walking around the airport like that?

...

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