Gambling With Our Lives
2 Bears, 1 Cave with Tom Segura & Bert Kreischer
September 1, 2025
- Don’t miss out on all the action this week at DraftKings! Download the DraftKings app today! Bert and Tom are BACK in the Cave!
Speakers Tom Segura, Bert Kreischer
TopicsComedySociety & Culture
Tom Segura (0:05)
Welcome to the final episode ever of 2 Bears 1 Cave. It was a blast while it lasted and we're here to sign off. We thank Stavvy and Chris DiStefano for taking over. We know you enjoy them and you will continue to enjoy them. Bert, good to see you.
Bert Kreischer (0:21)
Good to see you. Did you watch any other episodes?
Tom Segura (0:31)
I saw parts of it.
Bert Kreischer (0:32)
You don't watch any fucking podcasts.
Tom Segura (0:35)
That's true, but I did watch parts of it. I started the first one, I watched about 25 minutes of it and then I would pick up little parts of the other ones.
Did you watch them all?
Bert Kreischer (0:46)
I watched everyone. I watched everyone. Yeah, no. I watched the clips. I just know they were tracing us telling you the whole time.
Tom Segura (0:56)
They were great.
Bert Kreischer (0:57)
Stavvy is so fucking funny man.
Tom Segura (0:59)
They're both.
Bert Kreischer (1:00)
DeStefano is, I think Chris is fucking hysterical. I think he's one of the funniest guys alive.
Tom Segura (1:07)
Yeah, I totally agree. They're both just out of this world. Charismatic, funny. They're so entertaining.
Whenever I do a podcast with them, or even see them socially, it's always nonstop laughs. They're fantastic.
Bert Kreischer (1:21)
Did you see Chris on Hosting Kimmel?
Tom Segura (1:23)
I did. I watched his monologue, yeah.
Bert Kreischer (1:25)
He was great.
Tom Segura (1:26)
Fantastic.
Bert Kreischer (1:27)
His monologue was so natural.
Tom Segura (1:29)
Yeah, he's the man dude. So fucking funny.
Bert Kreischer (1:33)
What do you think the model's gonna be for saving the late night genre?
Tom Segura (1:36)
I think it's done.
Bert Kreischer (1:37)
You think it's done?
Tom Segura (1:38)
I don't think, well, I mean, unless they complete, like, here's the thing. When we were kids, you know, there was 25 channels and then the late night format was the place for this comedy, to see celebrities, to have these conversate, like, you know, it was access to all that world. Now, you know, people follow those same people on TikTok, on Instagram, on podcasts and videos. And they have access that is, like, more authentic and more detailed than a four minute panel conversation. Like, they're just, that whole younger generation is not like, oh, I can't wait to see Sydney Sweeney on a late night show because they can, like, watch her engage in a more, like, authentic way, detailed way through all these other outlets. So I just feel like they have to, they have to reframe the format.
Bert Kreischer (2:36)
But ultimately, everything is clips. This is a really fascinating jumping off point.
Tom Segura (2:41)
They make those shows for clips.
Bert Kreischer (2:43)
They make them for clips.
Tom Segura (2:43)
That's what they make, yeah.
Bert Kreischer (2:45)
I mean, I listened to someone talk about making a TV show, and I heard the guys say, are we doing this in vertical because people will only watch the clips? And then I was like, did you just pitch shooting a TV show in vertical? Like, so that you can get the clip? Because, I mean, honestly, I mean, everything's just clips. Kids only watch clips. And so, and what's funny is the late night format is clips. That is what they're trying to do is make the most interesting thing, the thing you talk about. So they are trying to pre-make the clip for you to watch, but it needs to be longer format to get the clip in a weird way.
Tom Segura (3:26)
Yeah. Yeah. I just, I feel like that type of the late night show, to me, if it hasn't run its course, it's, it's running it. I mean, I don't see ten years from now, us having that same format. I just don't. I think it has to, it has to evolve into something else. They have to rethink it.
Bert Kreischer (3:46)
Don't you feel, okay, here's the question. The first question is, how did you feel not having a podcast for a month, two months?
Tom Segura (3:54)
Fantastic. It was one of the best. It was the best. I would love to never do this again.
Bert Kreischer (3:58)
It was the greatest feeling I've ever had in my life. To not, you know, so funny, I've never been funnier in my entire life.
Tom Segura (4:09)
Then when you were there?
Bert Kreischer (4:10)
When I was there, casually funny, just talking to people and making people laugh. And I think because I'm talking so much, I forgot what it's like to be a regular person in conversations with people, and be spontaneously funny.
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