
The Anatomy of a Failed Comedy Podcast (Tom & Bert)
Patrick Cc:
Two extremely successful comedians, Tom Segura and Bert Kreischer, recently took a six-week break from their podcast that was already dropping in views. But what happened while they were gone made them realize their entire audience has officially turned on them.
We read the comments too. We're not going to save the show.
What took place in their absence was so bad that their comeback episode was originally titled We're Sorry We're Back. However, instead of listening to their fans' reasonable criticism, they ignored it, and went right back to doing the same thing that pissed off their audience in the first place. Now their podcast is in a worse position than it was before, and it's only a matter of time before two of the highest selling comedians in the industry have to shut down their show.
Welcome to the final episode ever of Two Bears One Cave. But this was possibly a
long time coming because only a few episodes into Tom and Bert's Two Bears One Cave podcast fans were already starting to notice some problems. You have to understand that the dynamic between Tom Segura and Burt Kreischer was originally a perfect match. Tom garnered a diehard fanbase online through his podcast, Your Mom's House. One of their legendary ongoing segments was called the Cool Guy Club.
Tom and his comedian wife, Christina P, would find bizarre, cringeworthy clips of guys online who had extremely questionable lifestyles. Like Robert Paul Champagne, who would publicly request that strangers have ex with him, dox himself sharing his address and personal information, which Tom and Christina Pee shared with their millions of fans.
If you're a hot black guy, you wanna f*** me at $23.95. If you wanna move in, you can move in but you gotta be I mean I need to be a lot man get free food free rent and everything else man here's a deal man men from jail homeless or um you're a thug want to come move in a friend can move to man free rent you can lease in a key me piss on me beat me a home you
know you see me when I come over today. Try it out. Try it out, man So stuff like that and who is he? He's that guy. His name is a Robert Paul champagne. He lives in New York
You could visit him when you're home. Another cool guy was Tony John's Utah's most infamous ladies, man
You know like dead ass though like breakups are hard. Don't get me wrong ladies ladies and gents playboys and playgirls
Breakups are hard Don't get me wrong ladies, ladies and gents, playboys and playgirls. Woo!
Breakups are hard, we gotta realize.
Holy sh**, I think I auditioned for this.
Tom didn't just laugh at these guys, he committed to the bit in a way that blurred the line between mockery and admiration. He would mimic their voices, turn their words into catchphrases, and talk about them as if they were legendary figures worthy of respect. It was obviously sarcastic, but Tom's ability to both a ridicule and celebrate them at the same time made the cool guy club feel less like a roast and more like an initiation into an inside joke that only
loyal listeners fully understood. Which is why when Tom and Bert Kreischer announced their Two Bears One Cave podcast, it was almost like Tom was doing an entire show with a cool guy. Now obviously, Burt was not as bizarre and unhinged as some of these random internet characters. He was also a popular comedian, who obtained a fanbase of his own through years of grinding
comedy clubs and of course being friends with Joe Rogan. But to Tom's fans, Burt embodied a lot of that same chaotic energy. Loud, unpredictable, indulgent, and always ready to overshare every embarrassing detail about his life.
I don't think she knows but I'm doing this thing where I tape my mouth shut at night to sleep because I think it'll stop me from snoring and last night I just started
suffocating. She woke up to someone like I was having a drink. Like that? And you're like, at least I'm not starving.
Oh, God, help me.
Get it out of my mouth.
Tom and Bert's most viral moment was only 36 episodes in when Bert admitted that he drinks two massive jugs of Kool-Aid every day. It caught Tom so off guard that his head nearly exploded from laughter.
You're drinking Kool-Aid to start your day?
Really?
It's so good.
What kind?
Red.
Kool-Aid is awesome.
It really is awesome. Take a little, pour a little something for yourself. It's watered down, it's not too bad.
You really drink Kool-Aid?
It's ice cold, yeah.
You are drinking Kool-Aid. Yeah. Yeah. Yeah. It's awesome They're like, good for that guy, he drinks a lot of water, it's clean.
Bert lives like how a kid would imagine being an adult is like. Basically the appeal of the podcast was Tom being the sharp, quick-witted observer who thrived on irony. Now Bert was the sort of goofy, idiot, lovable best friend at first, but it quickly turned into him being unsufferable. But first, as I've gotten older, I sometimes think it's time to start taking my own health
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and you can even score same-day appointments. to one year in, fans of Tom and Bert were questioning how long the two bears one cave formula could realistically last. Is anyone else losing interest in two bears? Tim and Bernt are still really funny, but the podcast has felt stale for some time now. It seems like at some point, they really started focusing on Bert's idiosyncrasies, which,
don't get me wrong, can be funny, but it's pretty much the same thing every week. And the longer it goes on, the more I feel myself getting annoyed by Bart and whatever zany thing he's doing this week. At the time, this was the minority opinion. Fans weren't looking for anything special. They found a level of comfort in just listening to two old friends play off each other and have one unserious conversation after another. The hate for Bert on this subreddit is ridiculous. Agreed, some of the guests have been pretty good, but I'm usually bored with them towards the end of the episode. Burt and Tom have chemistry that doesn't get old in my opinion. And even though a majority still loved the pod, it
only took a few episodes to realize how mind-numbing Burt's screechy laugh was. The audience was slowly turning on Burt, admitting that Tom was the only reason they would tune in every week. Burt Kreischer has been a comedian for decades. He is often criticized for being sort of a one-trick pony, because he constantly tells the same story about traveling to Russia when he was a college super senior, allegedly befriending
the Russian mafia, drinking enough vodka in front of the guys to impress them, and referring to himself as the machine.
The second the door opens and I'm face to face with a real Russian gangster, he just
looks at me and goes, STONE.
And everything I had planned on saying flooded out of my head, and all I said to him, I am
the machine.
However, Burt's silly drinking stories turned into genuine concern from Tom and the fans suggesting he may have a problem. About three days where he'll have, you know, six to eight drinks and then and then three
days where we're talking about usually 12 to 18 drinks, right?
Oh my goodness.
Is there any side effects with that? Anything happening?
There's a name for it. It's called alcohol use disorder, but a name alone doesn't tell the whole story. Bert, listen, we love you. I've never met you in person, but the world loves you. Like, don't, you don't need it.
This guy, I mean, it's wild that he's alive.
Theo Vaughn even tried to have a serious conversation with him about it, but Bert is notorious for justifying his actions by any means necessary.
Do you think that you're an alcoholic?
No, I've run it through the ringer a few times. Dr. Drew's my litmus and I've talked to him about he's like You're not an alcoholic. You just drink too much He's like alcoholism is different being powerless to alcohol is different than drinking a lot I drank a lot yesterday and I woke up in the middle of the night in a
Sizzle I'm so hot and all of a sudden my body went and sweat back to sleep. Nuh-uh. Yeah. Like almost like when a truck stops and it's like an addict does, we make rules for ourselves to make us feel like we have control over it.
At first, Burt's fit his a life of the
party persona. He even does all of his stand-up performances with no shirt on. But Bert constantly talking about alcohol went from funny to uncomfortable
to listen to. There's two types of people. There's addicts and there's partiers. Partiers stop when the when the party's over. over. And then addicts just never stop. That's true. I was like, oh yeah, I stop when the party's over.
Now it's one thing to occasionally laugh at a story about drunken chaos in college, and it's another to see a 50-something year old man literally romanticize drinking alcohol.
Come on in and get a drink, and I was like, no. I was like, goddammit man, if this is any other day I'd be like oh yeah yeah yeah yeah and I just double T'd us on a big last no-lime can I get a second one I'm
just gonna murder this one real quick it started looking like self-destruction playing out in real time Burt was gaining weight face getting bloated puffy and red and listening to him complain about it was not entertaining it was sad then you look at he's like me who wake up at midnight and then take The podcast turned into almost an intervention, with even their fan base expressing concern, which was honestly pretty wholesome It's nice to see that fans genuinely wanted to see Bert get better and to their surprise He eventually announced to everyone that he was going to get sober but only for 23 days
I'm going sober for for 23 days. What happens tomorrow that you're going for 23? Why I mean this I mean this heartfelt when we started this the sleuths who were like There's talking talking about Bert and I read the comments and they weren't hurtful They were like people concerned and I was like if that's how people are seeing me
Yeah, that's not how I want to be seen then after three weeks. He said this day 21. No booze. No sugar. No carbs and I feel Fantastic more energy thinking, not feeling hungry, he said his blood pressure dropped to the point where he didn't have to take his medication, Bert was shocked at how good his life could be. I'm down 40 pounds, I haven't had alcohol or sugar in 83 days, I've been primarily carnivore.
That all ends today. Despite all this great news and all of the positive effects of getting sober, Bert decided to celebrate his sobriety by getting absolutely hammered on the fully loaded cruise, which was a multi-day long private cruise slash comedy show that he spent one year planning. At some point the fan base just stopped feeling bad for someone who clearly doesn't want to help themselves, and as if that wasn't
insane enough they launched their very own vodka brand, which essentially incentivizes Burt to literally never put down the drink. On top of that, Burt had this chronic habit where he needed to cut people off, talk about himself, and then laugh loudly for minutes on end. Just look at Tim Dillon sitting there sober listening to Burt's fake laugh and genuinely looking like he wanted to leave the room as soon as possible. Unfortunately, Burt loves himself too much to ever realize how annoying he can be when
he talks and laughs in conversations with others. They are kinda opposites, Tim is highly authentic, even painfully so, whereas everything Burt does is contrived. Now a couple years into the pod, for many, Tom Segura was the only saving grace for Two Bears One Cave and it was holding on by a thread. But that was about to change. Tom went through some radical life transformations and started to lose the
appeal he once had as a comedian. He got in shape, moved to Austin, and became unfathomably wealthy. Which sounds admirable, but to longtime fans, it brought out the worst in him. Tom's self-deprecating, slightly unpolished comedic style was replaced by an unrelatable rich douche. And these days, fans can't really tell if he is joking anymore. When Tom Segura first started getting famous in the comedy world, his style was completely
different from the Tom we see today. If he wasn't pointing out his weight or talking about what he does in a hotel room in his spare time, he just presented himself as a regular guy, avoiding attention by any means necessary.
I used to wear hats a lot. You can't wear a hat anymore, not if it has an athletic logo on it.
Because some strange man that you've never met before will take you on a conversation
to nowhere. But after he ruptured his patellar tendon and fractured his humerus after jumping less than one foot off the ground, he realized he desperately needed a fitness transformation. Now there is absolutely nothing wrong with wanting to improve your health. The fans had been begging Burt to do the same for years, but it started to consume his personality. When Burt wasn't available for the podcast, Tom was bringing on athletes and powerlifters like Mark Bell,
which some fans admitted was still better than listening to Burt, whereas others wondered if this was even a comedy podcast anymore. I have no interest in weightlifting or bodybuilding, but this was still a fascinating conversation, so refreshing over the ramblings of Burt. I get that Tom and these dudes are pals, but all of these fitness guys are a serious snooze fest. At the same time, the two bears were exploding in fame and financial success.
Tom landed multiple Netflix specials, Ball Hog in 2020, followed by Sledgehammer in 2023, cementing him as one of the biggest comedians of this era. His ticket sales skyrocketed, selling out arenas all over the country. He moved his family into a six and a half million dollar Austin, Texas mansion down the river from Joe Rogan, bought luxury cars, and much of his humor was now centered around his wealth. Tom and Burt shared sweet stories about how they convince each other to buy expensive things because they
deserve it. watch going god damn it I love this and why I really love looking at it cheers me up I call Tom I said hey man I appreciate you sending me that message Leanne tried to convince me and I wouldn't do it but your message meant so much to me is that girl cool I go what are you doing he goes well you know I
sent you that message and I realized I shit applies to me too and if this was
all it was anybody criticizing Tom would just look petty and jealous. Most reasonable people agree that success should be celebrated. Being healthy and wealthy is the ultimate goal for the average American. However, Tom took it a bit too far when he started lecturing his audience on their broke mentality.
Every time we talk about like a watch or a car, I'll get like a bunch of messages from losers that try to tell me that I'm making them feel bad about their situation. You're in control of your own situation and your own feelings. So don't put it on me that you feel bad,
that I have something that, oh, but I'm struggling with rent this month. Figure it the fuck out Okay, like don't make my life be a problem for your life If you don't like it guess what you're not gonna be able to control what people talk about people are gonna talk about things That you don't have for the rest of your life so you can decide like okay
I won't look fine. Don't listen to me. Don't listen to that person anymore, but you have to control your own feeling. It's not on other people to make sure they don't talk about a topic that makes you feel bad. All right? Like I lost 20 grand gambling this weekend.
There was absolutely no comedy in this message. That was an honest confession of how he feels.
If you're still mad about this, just know that it's your mindset and you're thinking like a loser, but you don't have to. You can change the way you think, but you have to accept the way you're thinking right now is not going to get you anywhere. You're being bitter, you're being petty, you're insecure, you're not confident, and you can change that, but you have to be proactive.
If you just sit around, you only have what you have because of fans, so don't talk about
us like that. but you're still a loser. Now if Tom just went back to his typical comedic style, this could have easily been seen as just a joke. However, he seemed to be getting a kick out of making fun of poor people, which was extremely noticeable when he ranted on his podcast about using a washcloth, making a joke about it being a quote-unquote black thing, only to correct himself and just say it's for poor people. Well, did you try it even yet? No, I'm not going to do it. Well, you're just at you're just
anti-leg washes.
I'm not going to wash my legs and feet.
You think that's just a black people
thing?
Clearly.
Well, and he's the only one here who took the day off, washes his legs and feet. Now, I don't think that washing your legs and feet is for black people. I agree. I think the washcloth is a poor person
Thing because I I've only met poor so use them and after getting a ton of backlash He seemed to lean in even harder posting a video on Instagram Mocking his critics for judging his preferences and telling them they were just too poor to understand
So I've received a remarkable number of messages over the last few days from just countless poor people about the use of a washcloth in the shower. And it's kind of well-known, it's what poors do. And I made this comment on a podcast and so many people were upset, I mean really, really upset about it.
And I get it, it's part of their lifestyle or something. As if it couldn't get any worse, critics started pointing out that he was born into an upper-middle-class family and didn't really deserve to be gloating about how much he achieved with a safety net sitting right underneath him. Tom was raised rich by a successful guy. Him and Bert, who was raised by a rich lawyer and went to college for seven years, like to pretend they are normal dudes. These guys blow. It is true that Tom's father, also named Thomas Segura, worked for Merrill Lynch for 41 years, which is a global leader in wealth management and investment banking.
Tom has mentioned a few times that he used to be broke, which made his success something to cheer for. His fans love the idea of a comic grinding in small clubs, scraping by, and finally breaking through against all odds. But he wasn't exactly clawing his way out of poverty. He grew up with a financial safety net that most aspiring comics could only dream of.
That doesn't erase the hard work Tom put in, but it does kind of muddy up the story. To fans who once believed they were watching and supporting an underdog rise, his lectures now look more like a privileged kid who managed to get even richer. Once he started with the sh** on the poor stuff, I stopped watching anything with him in it. I don't understand why anyone other than rich a**holes would think someone being poor is funny. Tom became so wealthy that he couldn't seem to handle most minor inconveniences.
And when a staff member at American Airlines made him gatecheck his bag, Sagura absolutely lost it on Twitter. Dumb C-U-N-T from American Air made me gate check my bag so she feels the little power she has in her life. I get it, you win this round, C-word. Well your whining sounds like she made the right call.
Minor inconveniences. Oh the horror. All the poors and losers have the same response. Oh, you were inconvenienced, well you should accept it. That's what me and my dumb poor family have done for generations. This is why you're a poor. Tom deflected any criticism by just responding, poor.
The lowest level poors get upset, as they've been trained to do. When you point out their, happy to do what I'm told, servant mentality. They don't value time because their time is worthless. You are specs of shit on a washcloth and washcloths belong in the trash. Now to be fair, this is just text on a screen, so it is hard to interpret the tone or understand if there was any humor involved in these tweets. But after reading it a couple of times, it's
hard to see it as anything other than a rich guy just being an asshole. And this was a tipping point for many of Tom's long-term fans. Even the ones who thought his running pores gag was funny, they saw this Twitter rant as kind of a meltdown where he went too far. And all of this gloating about money, complaints about working class Americans, and pushing back against anyone criticizing him made the once down-to-earth comedian become the very thing he hated. And to see just how much his finances became a part of his identity, when Tom did a podcast with Joe Rogan, most of the comments were about money.
Is this video wage-restricted? My net worth is way too low to watch this. The poors were here. Now if this was all just some internet podcast drama, and it hadn't actually impacted their comedy, it would've been easy for fans to get over it. But once Tom and Bert got the chance to perform at the roast of NFL legend Tom Brady, it just felt like another mediocre bit from their These vodka salesmen are having a hard time reading the teleprompter. This was, by far, the least funniest thing from the night.
Fall from grace. They're done. By 2025, most of the original fanbase of Two Bears One Cave had checked out. View counts dropped over 70% going from 800,000 average viewers to just over 200,000. Most people felt that the duo had gotten lazy and only made podcasts every week because it was an easy way to make money. But feeling that it was
unnecessarily stressful, Tom convinced Burt to take time off for six whole weeks while they went on tour to focus on their new vodka brand and stand-up comedy. YMH Studios hired Stavros Halkias and Chris DiStefano to temporarily host the podcast. And this decision horribly backfired in a way that Tom and Burt could never have imagined. From the very first episode together, Stavros and Chris reminded the audience that a podcast is much better when comedians make a legitimate effort to be
funny. Instead of Bert's constant denial about his health and bragging about his hollow fitness goals, Stav and Chris were full of energy and showed genuine interest in the conversation. And both of them even admitted that they saw the podcast was failing and they couldn't stop the ship from sinking
Listen guys, we're excited to do this, but we know what you know, we read the comments too. We're not gonna save the show No, the show is absolutely done This is like when a marriage is failing so you adopt two fun children
You know what I'm saying?
Tommy and I are like the two cool Vietnamese kids that Brad Pitt and Angelina Jolie adopted a month before they got divorced.
The 2 Bears fanbase clearly did not miss Tom and Bert. They may have not even known that they were gone. Because Chris and Stav got more views than Tom and Bert had received in years. First 2 Bears episode I've clicked on in years. The first 5 minutes already has surpassed the last 2 years of this show. This was great.
Tim and Bert, please never come back. Not only were Stav and Chris making better jokes, but the audience's hatred for Bert's delusions and Tom's ego was so strong that Chris and Stav were saving the show by simply roasting Tom and Bert every chance they got. And Tom and Bert's producers actually went out of their way to help the boys do it.
I mean that's... Smashable. That's insane that he's saying that. I'm hotter than Leanne. He's hotter than- he thinks he's hotter than his wife. Yeah, my chick is like Colton. Yeah, I look like such a nice girl. You're the one who's like, come with me, I'll show you how to get a man. That's what it looks like.
In the following weeks, Stav and Chris's dynamic was so good that fans begged for them to stay, but unfortunately, that wasn't going to happen. They joked about not even wanting to do the show at all, and Chris even admitted that he wanted to intentionally sabotage the show by spending the last five minutes giving Stav a massage.
Don't start getting feelings for us. We're not sticking around. We're not sticking around. Here's how committed we are to making sure this episode is awful. We want you to stick around to the end because the last five minutes I'm gonna
massage Stavi. This is not a joke at this point. This podcast is 1,000 times better with these two. This is exactly what this podcast needed to become a totally different podcast. By the last episode, Chris and Stav were more comfortable than ever. They honed in on what the audience wanted and were spending most of their time messing around and criticizing the dynamic between Tom and Bert.
Chris compared Stav's purple shirt to Bert's alcoholic liver and how they just share information about their personal lives that other family members would have liked to keep a secret.
By the way, you do look nice in that purple shirt,
which is probably the same color as Bert's liver.
But at this point point Stav and Chris were counting the minutes until the show was over. They even made a surprise phone call to Burt Kreischer and somehow he managed to bomb over the phone on his own podcast. They basically asked Burt what they should talk about on the podcast and Burt's suggestion was so terribly unfunny yet somehow Chris and Stav turned it into an actually decent joke. Is that like when you guys break down other comics?
That's always been fun for us. You know, Tom and I have a vodka, but Joe's diversified himself so much that I think having a vodka is just hack these days that you need to have a real brand based on the comic. So I was gonna have you go through a list of comics
and say really what their fans would buy based on who they are.
Okay.
Okay. Like Sam, Sam Morrell has, don't take a cap, but what could he really sell to people based on his dull personality? Maybe a wax kit? A wax kit? A wax kit? Yeah. You know what I mean? What would his fans go, oh yeah, that is what I love about Sam.
Yeah, he could sell like Nick's jerseys to special needs kids. Yeah. Ultimately, the bit felt like a sad conversation with a drunk dad rather than a back-and-forth with a professional comic. And sadly the six weeks flew by extremely fast and it was time for Chris and Stav to pack up and head home. Don't cry because it's over, smile because it happened. The past six weeks I've watched more Two Bears One Cave than I have in the previous year.
When Bert and Tom returned it was like the life was sucked out of the room. Despite them taking a much-needed break, they came back with low energy, in fact, no energy. Just they seemed bored. They seemed like they didn't even want to be back. From the very beginning of the return episode, Tom seemed to realize that the replacement
might have been a mistake, cracking a couple of jokes for the disappointed audience. Did you watch any other episodes? Uh, I would watch like- No you did not! I saw parts of it.
You don't watch any f***ing podcasts.
To give Burt the benefit of the doubt, he talked about how he watched every single episode with Chris and Stav and thoroughly enjoyed it as a fan. Tom on the other hand, didn't watch any of the episodes of his own podcast and quite frankly seemed like he just didn't care. Before Tom and Bert took their six-week break, they were averaging a little over 200,000 views per episode. Stav and Chris nearly doubled their view counts during their substitution, and now that Tom and Bert are back, they haven't even cracked 200k. It seems like the audience heard what a
comedy podcast was supposed to be like and realized that Tom and Bert just don't got it anymore. Near the end of their comeback episode, all you're watching is dead air, with Tom and Burt picking up their phones and talking about later plans. I think it's probably time to wrap it up, boys. It's rare to see an audience legitimately turn on comedians, especially since they usually have some of the most loyal fanbases, but seeing how great a podcast duo can be with Kris and Stav was the final nail in the coffin for two bears.
Is this a sign that they maybe should pack it up? Yeah. Will they actually end the podcast? Will they actually end the podcast? Probably not.
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