Is White-Face Cool Again? | 2 Bears, 1 Cave - 2 Bears, 1 Cave with Tom Segura & Bert Kreischer

Transcript

Bert Kreischer (0:00)

100%.

Tom Segura (0:05)

Welcome to another episode of Two Bears One Cave. We apologize, but we are back. Yes. We've reached out to Stavi and Chris and other people, and we'll see what their avails are, but for this week, it's us.

Bert Kreischer (0:24)

We're so sorry, guys. We're so sorry. I feel so bad that you guys have to listen to us.

Tom Segura (0:31)

I do, too. And you don't have to.

Bert Kreischer (0:32)

That's the only thing a little hard this week because I was like, yeah, yeah, yeah. Cause I was like, well, there's a lot going on, but I was like, I'm going to bring in good talking points.

Tom Segura (0:42)

Good talking points. Good energy.

Bert Kreischer (0:43)

Good energy. We're starting with blackface.

Tom Segura (0:47)

Okay.

Bert Kreischer (0:47)

Or not blackface. Whiteface. Drew Ski.

Tom Segura (0:50)

Oh, yeah, yeah, yeah.

Bert Kreischer (0:51)

We can talk about Drew Ski. We can talk about. Would you die for your country? Great conversation points right there. Us being only fans. Pimps. Great idea. Great idea.

Tom Segura (1:00)

That's good. That's a good idea.

Bert Kreischer (1:01)

We're going to talk about Florida State and. And how Leanne and I got into a huge fight moving Isla into college this past.

Tom Segura (1:09)

Like, over the weekend.

Bert Kreischer (1:10)

Over the weekend.

Tom Segura (1:12)

Oh, that'd be. I'm very excited. I will say this. I got to tell you. There's certain, like, formats, mediums that people are just so good in.

Bert Kreischer (1:20)

Yeah.

Tom Segura (1:20)

Dude. Drew doing these sketches that he's been doing for a long time now.

Bert Kreischer (1:25)

Summary

Episode Overview

Title: Is White-Face Cool Again?
Podcast: 2 Bears, 1 Cave with Tom Segura & Bert Kreischer
Release Date: September 8, 2025
Studio: YMH Studios

In this episode, comedians Tom Segura and Bert Kreischer dive deep into comedy controversies around "whiteface," discuss the genius of modern internet sketch comedians, reflect on patriotism and generational change, banter about sports fandom, and brainstorm million-dollar podcast stunts—like managing an OnlyFans account. The tone is irreverent, unfiltered, and packed with the signature energy fans expect from the duo.

Key Discussion Points and Insights

1. Drewski, Whiteface, and Race in Comedy

[00:43 – 12:28]

The main discussion centers around Drewski, a comedic performer known for his "whiteface" NASCAR spoof, and the reactions it sparked online.
Bert and Tom praise Drewski’s commitment and transformative ability in sketch work, comparing his method and talent to comedy legends.

"He is the future right now. If you're sitting on your couch going, I want to get into comedy, don't ask me and Tom… Ask Druski."
— Bert Kreischer [01:28]
Dive into how the sketch's comedic success was due not only to Drewski's acting but also the hair and makeup team’s “sunburnt white guy” look.
Bert reflects on social boundaries in comedy, questioning if he or Tom could pull off “blackface,” “yellowface,” or “brownface,” and how much of the character’s success depends on nerve and context.
They riff on the complexity of racial humor in America, raising questions about offense, context, and who can (or can’t) take a joke.

"You can't be a black guy, not use the N word. It's the best word they say."
— Bert Kreischer [08:33]
Discussion of internet outcry over Drewski’s sketches, the shifting lines in comedy, and how certain online communities have rallied around him.

2. The Rise of Internet Streamers and Changing Media

[11:13 – 14:26]

Bert marvels at the new generation of internet entertainers—Kai Cenat, Aiden Ross, etc.—and the astronomical money and influence these live streamers wield.
Tom is more skeptical, suggesting it’s less about genius and more about timing and exploiting a new format.
Recognition that this new form of streaming/entertainment is reshaping how young people engage with content and each other, even leading to shifts in career aspirations away from traditional paths like military service or heroism.

3. Patriotism, Sacrifice, and Generational Shifts

[16:49 – 23:43]

Both comics reflect (half-seriously) on whether they’d be willing to die for their country, with Tom leaning into the sense of obligation passed down from his Marine father, and Bert flatly admitting he wouldn’t.

"No, I'm being honest. I mean, dead honest. Like there's, and I mean that as a compliment to everyone in the military is that I don't have the thing they got."
— Bert Kreischer [19:06]
Bert laments how modern culture rewards personal glory more than selfless heroism; together they muse on how cushy their lives are compared to generations past.
They riff (with characteristic gallows humor) about living in different eras, referencing the Civil War, and imagining absurd alternate histories.

4. Sports Fandom and Emotional Investment

[38:23 – 49:54]

Tom shares his deep emotional attachment to college football and Florida State University (FSU). For him, true fandom involves suffering and loyalty, not just casual interest.
Bert recounts giving a pre-game speech at FSU and the rush of connecting with tens of thousands of fans.

"When that spear went into that Seminole head, I started crying and I didn't know why."
— Bert Kreischer [43:18]
They reminisce about legendary college football atmospheres and fantasize about touring top schools for games.
Banter about their respective touring schedules, the joys and pains of traveling, and the logistics of live shows.

5. OnlyFans Million-Dollar Scheme and Podcast Stunts

[51:03 – 59:14]

Bert pitches a new podcast stunt: he and Tom managing a fan’s OnlyFans account, turning an unknown creator into a star by managing/pimping their content.
They debate whether to launch a creator “from scratch” or help someone with a modest following.
Vision is to make it interactive, breaking standard OnlyFans molds and involving their fan community.

"We will help them build… promote the shit out of them. But we take a very small cut."
— Bert Kreischer [52:12]
They joke about the boundaries of what content to produce, bringing their unfiltered brand to adult content management.
Plan is to solicit applications via email/DMs, with Bert excited (and likely overwhelmed) by anticipated responses.

6. Personal Anecdotes & Family Dynamics

[59:20 – 65:52]

Bert shares a chaotic, humorous story about moving his daughter into college, getting roasted by his family for claiming to be “one of the strongest men in the city” while failing to move a heavy armoire.

"I am one of the strongest men in that fucking city, without a doubt."
— Bert Kreischer [62:37]
The segment highlights Bert’s tendency for mythmaking and comic bravado, and how his family tempers him.

Notable Quotes & Memorable Moments

On Drewski’s “Whiteface” Comedy

“That was fucking phenomenal. That was so good. A sunburn. A wife beater sunburn on a black guy is chef's kiss. It was so good.”
— Bert [02:52]
“He murdered it. Look at this. When she smokes out of his lap. You need to listen to your nana. Go ahead, baby.”
— Bert [04:49]

On Modern Internet Stars

“They have single handedly recreated entertainment.”
— Bert [11:51]
“I just don’t think they’re geniuses. I just think they’re, you know, right time, right place.”
— Tom [11:35]

On Patriotism and Generational Change

“I think today we have a culture… who would only do something selfless if they got credit for it.”
— Bert [20:55]
"Our life is. It's so nice. It's really great."
— Tom [23:43]

On College Football and Fandom

“It was so goddamn exciting. I mean it's why I love sports, and it's why I love college football."
— Tom [42:22]
“If I had to Groundhog Day one weekend, I'd do that weekend every day.”
— Bert [42:32]

On the OnlyFans Pitch/Stunt

“We're going to be an OnlyFans, content creators. Pimps.”
— Tom [51:10]
“There's a way to create an OnlyFans account that's very fun, that's interactive. That's not just like, hey, I want to watch you fuck this dude…”
— Bert [56:07]

On Bert’s Strength and Family Challenge

"I'm one of the strongest men in this fucking city."
— Bert [61:38]
"Well, no, it does mean something. It means that you're pretty strong, dude. You have a big back. You look like an ox, dude."
— Tom [63:02]

Timestamps for Important Segments

| Timestamp | Segment Topic | |-----------|--------------| | 00:43–12:28 | Drewski, whiteface, and comedic boundaries | | 14:26–16:49 | Ad reads (skipped) | | 16:49–23:43 | Generational views on patriotism and heroism | | 38:23–49:54 | Sports fandom and the Florida State experience | | 51:03–59:14 | OnlyFans management scheme | | 59:20–65:27 | Family tales: Bert’s armoire saga & family dynamics | | 65:52–67:29 | Upcoming tour dates, OnlyFans submissions, wrap-up |

Closing Thoughts

This episode is a freewheeling, joke-strewn hour-plus that jumps from deeply personal moments (Bert's family, Tom's football suffering) to provocative riffs on race, comedy, fame, and modern culture. The hosts' chemistry shines as they egg each other on, reveal insecurities, and pitch wild new ventures, all in their signature, boundary-pushing comedic style. The energy and banter make even the wildest tangents compelling for diehard fans and newcomers alike.