2 Bears, 1 Cave with Tom Segura & Bert Kreischer

By YMH Studios

Weekly, comedian best friends Tom Segura and Bert Kreischer get together in the bear cave at YMH Studios to do what bears do: make each other laugh.... more

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FAQs about 2 Bears, 1 Cave with Tom Segura & Bert Kreischer:

How many episodes does 2 Bears, 1 Cave with Tom Segura & Bert Kreischer have?

The podcast currently has 301 episodes available.

2 Bears, 1 Cave with Tom Segura & Bert Kreischer episodes:

June 02, 2025 Tom's Dad STOLE Dynamite & BLEW UP A Bridge w/ Barstool Big Cat | 2 Bears, 1 Cave
Check out the newest podcast from YMH Studios "Not A Damn Chance"! Hosted by pro skateboarder Neen Williams and Michelin-starred chef Phillip Frankland Lee https://www.youtube.com/watch?v=ihy5odp5G9A
SPONSORS:
- Make life easier by getting harder and discover your options at https://BlueChew.com! And we’ve got a special deal for our listeners: Try your first month of BlueChew FREE when you use promo code BEARS -- just pay $5 shipping.
- If your revenues are at least in the seven figures, download the free e-book “Navigating Global Trade: 3 Insights for Leaders” at https://NetSuite.com/BEARS.
- Sponsored by BetterHelp. Our listeners get 10% off their first month at https://betterhelp.com/bears
This week on 2 Bears 1 Cave, Tim Segura and Bert Kershire are LIVE from the Barstool Chicago studio and share some stories of their latest shenanigans in the Windy City. The Bears also talk about bombing in Hawaii, jokes about slurs, fathers, women fading, whatever's going on in Bert's mouth, plus the internet hate for WNBA player Angel Reece and alleged royal Meghan Markle. The Bears are then joined by Big Cat who talks about stuff his kids are into lately and his favorite hobby aka gambling. Speaking of which, he also teaches the Bears about Dana White's infamous Tunnel of Chaos, before they pivot to the series "MobLand", and Tom shares a story about almost buying Dr. Dre's house. Bert also trash talks Tom's home base for some reason and compares us...I mean...it, to an abortion clinic or a dentist office, which, let me say is totally an exaggeration....I love working here. Enjoy the episode!
2 Bears, 1 Cave Ep. 291
https://tomsegura.com/tour
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https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:02:36 - Chicago Shenanigans
00:16:06 - Mouth Stuff
00:19:39 - Bombing Hawaii
00:29:01 - Friends
00:36:51 - Internet
00:43:28 - Women
00:49:04 - Big Words
00:59:18 - Mandela Effects
01:03:51 - Kids Stuff With Big Cat
01:12:09 - Gambling
01:20:42 - MobLand
01:24:17 - Work From Home
01:30:37 - Big Cat's Other Interests

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1h 40min
May 26, 2025 Tom Shows Harland Williams His Chocolate Starfish | 2 Bears, 1 Cave
Check out the newest podcast from YMH Studios "Not A Damn Chance"! Hosted by pro skateboarder Neen Williams and Michelin-starred chef Phillip Frankland Lee
SPONSORS:
- Get started at https://factormeals.com/bears50off and use code bears50off to get 50% off plus FREE shipping on your first box.
- Make friends and grab some merch at https://www.drinkporosos.com/
This week on 2 Bears 1 Cave, Bert is on a retreat in Istanbul so Tom Segura is joined by the brilliantly bizarre Harland Williams for an unhinged episode packed with supposedly true stories, bootyholes, and too many farts. Harland kicks things off by reminiscing about fingering calamari and the first time someone touched his arse—with a thermometer. Tom shares the traumatic moment he had to show a friend his infamously hairy sphincter... and yes, he ends up showing Harland too.
Surprisingly, the conversation spirals into absurd territory with erotic drawings, smut searches, fart-catching attempts, a Dominican dick flash, and a deep dive into Enny’s alleged fondness for buttholes. Harland doesn’t disappoint either—he reacts to fart videos, tells a story about dating Madonna, and looks forward to tanning with Tom. The two also talk about creativity, recreational drugs, Harland's distrust of nicotine pouches, the anthems of both Canada and Texas, plus playing doctor, and horseshoes with neck pillows. Oh, and Harland names his favorite dictator. Stick around to find out if Harland ends up eating Tom.
2 Bears, 1 Cave Ep. 290
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:02:55 - Arses & Calamari Rings
00:14:34 - So Much Hair
00:26:10 - What's Going On With Canada?
00:31:24 - Measurements, Buzzes, & Vices
00:41:37 - Favorite Dictator
00:51:49 - Dating Madonna
00:55:46 - Clip: Baddie Farts
00:56:49 - Play Back The Tape
00:58:13 - Clip: Fart In One
00:59:29 - Tanning & Tour Dates
01:05:45 - Gas, Gashes, & Gruesome Videos
01:11:48 - Harland Wants To Eat Tom

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1h 20min
May 19, 2025 Bad Thoughts About Meghan Markle | 2 Bears, 1 Cave
SPONSORS:
- Grab your tickets at https://NASCAR.com/tickets. If you can’t make it, grab a beer and your friends, find your seat on the couch, and gear up for some of the best racing in the world at Charlotte Motor speedway. Tune in to the Coca Cola 600 this Sunday at 6:00 PM Eastern
- Brought to you by BetterHelp. Visit https://betterhelp.com/bears to get 10% off your first month
- Sign up for a $1 per month trial period at https://shopify.com/bears.
- Get your summer savings and shop premium wireless plans at https://mintmobile.com/BEARS.
This week on 2 Bears 1 Cave, Tom Segura and Bert Kreischer go deep on Tom’s new Netflix series Bad Thoughts — a disturbing, hilarious, and brilliantly unhinged ride that Charo absolutely hated. The Bears talk about favorite sketches, behind-the-scenes moments, bloopers, and why Bert is both joking and not joking about not being cast.
They dive into the art of acting, working with writers, and getting lost in characters — plus Bert’s dream roles if he had been invited. Also: Tom's Italian guy character, hair insecurity, Kevin James dying his beard, and Tom's preference for a show that doesn't look like a comedy. Elsewhere, Bert shares his Post Malone + Jelly Roll solo mission, NASCAR plans, and recent attempts at eating clean and not drinking again. There’s debate over royal titles, Meghan Markle, Prince William, and a killer impression of the royal family worrying about baby skin tone. Plus: Bert’s mail opening trauma, how he weighs himself, cauliflower pizza, bar takeovers, and why Tom might actually like who he is. It’s full sketch comedy breakdown meets chaotic Bear therapy—don’t miss it.
2 Bears, 1 Cave Ep. 289
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:00:20 - Tom Talks Bad Thoughts
00:13:50 - Cinematography & Awkward Sex Scenes
00:21:45 - Casting Choices & Putting Friends In Movies
00:33:23 - Tom's Acting, Bert's "Sobriety", & NASCAR
00:40:20 - The Royals & Meghan Markle
00:55:01 - Bills
01:03:01 - Big Boys
01:09:31 - Wrap Up

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1h 9min
May 12, 2025 Welcome to 2 Bears, 1 Cave with Tom Segura & Bert Kreischer
Weekly, comedian best friends Tom Segura and Bert Kreischer get together in the bear cave at YMH Studios to do what bears do: make each other laugh.

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2min
May 12, 2025 Ripping Beers & Running 5K's w/ Jason Kelce, N.O.R.E, and Beau Allen | 2 Bears, 1 Cave
SPONSORS:
- Head to https://bubblycleaning.com/Bears to get your first 3 hours of cleaning for only $19. Thanks so much to Bubbly Cleaning for sponsoring this episode!
- Head to https://acorns.com/bears or download the Acorns app to get started.
- Start your free online visit today at https://Hims.com/BEARS.
- Upgrade your wallet today! Get 10% Off @Ridge with code CAVE at https://www.Ridge.com/CAVE #Ridgepod
- Order a bottle of Por Osos and some killer merch online https://drinkporosos.com
This week on 2 Bears 1 Cave, Tom Segura and Bert Kershire are LIVE from the 2 Bears 5k in Tampa Bay Florida! They aren't alone either, the bears are joined by not one, not two, but three guest bears! Joining Tom and Bert are rapper/running enthusiast N.O.R.E, as well as, former NFL players/Super Bowl champs, Jason Kelce and Beau Allen. The group all get together to talk about the real challenges of the 2 Bears 5k, who the best drinkers are, running, nicknames, dictators, Hype Williams, stupid purchases, and so much more. Enjoy the show!
2 Bears, 1 Cave Ep. 288
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:04:17 - N.O.R.E
00:14:48 - Japanese Whiskey
00:20:12 - Beau Allen & Jason Kelce
00:26:33 - The Best Drinkers & Worst NFL Matchups
00:35:33 - Nicknames & Dictators
00:42:02 - Hype Williams
00:45:39 - NFL Rookies
00:53:51 - Drinking Before A Big Game
00:58:23 - Stupid Purchases
01:06:16 - Wrap Up

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1h 10min
May 05, 2025 MrBallen Traumatizes Tom Segura | 2 Bears, 1 Cave
Check out MrBallen’s channel here: https://www.youtube.com/@MrBallen

SPONSORS:
- Buy Jack Link's Duos at https://JackLinks.com/DUOS or at your local convenience, gas, grocery store or subscribe and save on Amazon.
- Get up to $200 off Square hardware when you sign up at https://square.com/go/bears! #squarepod
- Make life easier by getting harder and discover your options at https://BlueChew.com! And we’ve got a special deal for our listeners: Try your first month of BlueChew FREE when you use promo code BEARS -- just pay $5 shipping.
- Brought to you by BetterHelp. Visit https://BetterHelp.com/bears to get 10% off your first month.
On this episode of 2 Bears, 1 Cave, Tom Segura is joined by the legendary storyteller himself—MrBallen! Get ready for an epic conversation as they dive into some of the wildest true crime mysteries and horror stories, including the chilling unsolved case of the Yuba County Five and a gruesome incident on an oil rig that will haunt your dreams.
They also explore mind-blowing topics like habitable exoplanets, Katy Perry’s space adventure, and MrBallen’s incredible journey from Navy SEAL to YouTube sensation.
Don't miss this one—it's a mix of mystery, mayhem, and a whole lot of laughs.
2 Bears, 1 Cave Ep. 287
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:01:15 - The Strange, Dark, & Mysterious World Of MrBallen
00:07:29 - Why True Crime?
00:14:03 - The Stories That Stick With You
00:28:10 - The Yuba County Five
00:35:45 - Exoplanets
00:40:57 - Katy Perry In Space
00:44:47 - First Day On Seal Team 2
00:58:44 - New Career Path
01:10:06 - Grenade Moment

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1h 19min
April 28, 2025 The Blue Origin Broads Backlash w/ Thomas Lennon | 2 Bears, 1 Cave
Check out Bert's new special "Lucky" streaming on Netflix!
The 2 Bears 5k is this Sunday! There’s still time to sign up and join us in Tampa at Raymond James Stadium! Sign up at https://www.2bears5k.com/#intro
SPONSORS:
- Go to https://shipstation.com and use code CAVE to sign up for your FREE trial.
- Learn more about Lightstrike at https://Drinklightstrike.com or follow on TikTok and Instagram @drinklightstrike.
- You can find Cremo’s new line of antiperspirants and deodorants at Target or https://Target.com
- Get started at https://factormeals.com/bears50off and use code bears50off to get 50 percent off plus FREE shipping on your first box.
- Head to https://policygenius.com to get your free life insurance quotes and see how much you could save.
This week on 2 Bears 1 Cave, Bert Kreischer is joined by legendary funnyman and certified bear Thomas Lennon for one of the wildest rides yet. No stranger to confrontations, Thomas tells Bert some stories about a fight he got into in the real-world and the internet. They dive into the Amazon reviews of Mein Kampf, unpack the all-female Blue Origin space flight, and debate which celebs should be launched into orbit next.
Thomas also opens up about working with Christopher Nolan, shares the weirdest thing he’s ever used his fame for, and the two squirm over some spelunking stories. The two also discuss claustrophobia, Tom's basketball injury, suicide pods in Switzerland, and whether getting beat up by a woman is a fair fight. From film criticism to Karen moments, to the legendary Pink Palace, this episode has it all!
2 Bears, 1 Cave Ep. 286
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com
Chapters
00:00:00 - Intro
00:01:23 - Mein Kampf
00:06:34 - Women In Space
00:11:03 - Happy Endings
00:18:18 - Back To The Lady Astronauts
00:22:37 - Thrill Seeking
00:26:00 - Caves
00:35:53 - A Funny Death
00:40:05 - Fame
00:45:47 - Tom's Broken Body
00:49:37 - Swiss Unalive Pods
00:56:38 - The Man Who Would Be King
00:59:44 - Christopher Nolan Movies
01:07:24 - Film Criticism
01:22:27 - Confrontations
01:34:57 - Cop Stuff
01:39:34 - Karen Moments
01:42:57 - Can't We All Just Get Along
01:49:38 - Couples Therapy & The Space Draft
01:55:31 - Body Acceptance

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2h 3min
April 21, 2025 Sampling Your Own Sauce | 2 Bears, 1 Cave
Check out Bert's new special "Lucky" streaming on Netflix!

The 2 Bears, 5K in Tampa is less than 2 weeks away! Sign up at https://www.2bears5k.com/#intro

SPONSORS:
- Shop data plans at https://MINTMOBILE.com/BEARS.
- Sign up for a $1 per month trial period at https://shopify.com/bears.
- Brought to you by BetterHelp. Visit https://betterhelp.com/bears to get 10% off your first month.

This week on 2 Bears 1 Cave, Bert Kershire and Tim Segura are hooked up to IV's as they recover from their gay bar takeover and all the love the received from all those hungry bears. They talk Instagram FOMO, the magic of minority women making meals for their husbands, a chola influencer named La Sleep that Bert is obsessed with, and the performative nature of social media. They also talk about the appeal of the Kelce brothers to gays, share the unique name of a cocktail that was invented at the takeover, debate which group of people gives the best compliments, and finally they tackle the subject of sampling your own sauce, which means exactly what you think it means. Enjoy the show!

2 Bears, 1 Cave Ep. 285

https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com

Chapters
00:00:00 - Intro
00:00:56 - Post Takeover IV Drip
00:08:56 - Watches
00:15:31 - Car Guys & Dogs
00:21:15 - Bert Is A Mexican Woman
00:28:28 - Gay Black Couple Meals
00:33:10 - The Cholo Life
00:36:51 - Instagram FOMO
00:45:51 - Gay Compliments
00:53:53 - Kelce Bears, UTI's, & Sampling Your Own Sauce
01:01:22 - Clip: Drinking An Ari Cocktail
01:08:35 - How Much To Taste?

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1h 17min
April 14, 2025 Bert Choke Slammed Two Dudes | 2 Bears, 1 Cave
Check out Bert's new special "Lucky" streaming on Netflix!

The 2 Bears, 5K in Tampa is less than a month away! Sign up at https://www.2bears5k.com/#intro

SPONSORS:
- Start your free online visit today at https://Hims.com/BEARS.
- Today get 20% off your DeleteMe plan by texting CAVE to 64000.
- Shop data plans at https://MINTMOBILE.com/BEARS
- Head to https://acorns.com/bears or download the Acorns app to get started.
- Get 20% OFF + Free Shipping @MANSCAPED with promo code BEARS at https://manscaped.com! #ManscapedPartner #TCSociety

Tom and Bert are back in the cave and things get spicy fast.
This week the Bears dive into alternative p*rn genres you didn’t know you needed, celebrate the beauty of international women, and break down the logic and logistics behind the noble art of “homie head.” They also mentally prepare for a Por Osos gay bar takeover and talk the top 5 hot chick accents. Next, Bert recounts his unforgettable Monday Night RAW moment where he went full low-IQ adult and choke slammed two dudes on live TV! Then it’s onto arranged marriages, glory holes, and other socially important topics. Pack a towel, this one gets sweaty.

2 Bears, 1 Cave Ep. 284

https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com

Chapters
00:00:00 - Intro
00:02:23 - Alternative P*rn
00:07:41 - Normalize Homie Head
00:14:11 - Por Osos Gay Bar Takeover
00:18:58 - Bert Choke Slammed Two Dudes
00:31:25 - The Wrestling Bug
00:40:15 - Retirement Community Idea
00:45:42 - International Delights
00:51:31 - Hottest Chick Accents
00:59:22 - Arranged Marriages
01:04:10 - Glory Holes, Milking Tables, & Sexy Nurses
01:09:51 - MSG & Summer Break
01:17:56 - Wrap Up

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1h 20min
April 07, 2025 Kill Tony Hits Netflix & Kyle Dunnigan’s Most Hated Impression | 2 Bears, 1 Cave
Check out Bert's new special "Lucky" streaming on Netflix!
Tom just announced Fall dates for his Come Together Tour at https://tomsegura.com/tour. Presale starts April 2nd, use code TOMMY.

Watch Kyle Dunnigan on Kill Tony on Netflix today!

SPONSORS:
- You can find Cremo’s new line of antiperspirants and deodorants at Target or https://Target.com
- Sign up for a $1 per month trial period at https://shopify.com/bears.
- Brought to you by BetterHelp. Visit https://betterhelp.com/bears to get 10% off your first month.
- Make life easier by getting harder and discover your options at https://BlueChew.com! Try your first month of BlueChew FREE when you use promo code BEARS -- just pay $5 shipping.

This week on 2 Bears 1 Cave we have Tom Segura and guest bear Kyle Dunnigan! After both appearing on "Kill Tony: Kill Or Be Killed", now streaming on Netflix, they've got some thoughts and reactions from that insane event to share with of you. They also discuss Kyle's weird dating history, his interest in taller women, and how he finds dates in a world of dating apps. Kyle also has a massive collection of impressions he unloads, including Caitlyn Jenner, RFK Jr, Joe Biden, and the infamous Bill Maher impression that Bill Maher just absolutely loves okaaayy. They also exchange stories about bombing at private events and Kyle tells Tom all about the time he worked Tony Robbins' weird birthday party. Lot of stories, lot of impressions, check it out!

2 Bears, 1 Cave Ep. 283

https://tomsegura.com/tour
https://www.bertbertbert.com/tour
https://store.ymhstudios.com

Chapters
00:00:00 - Intro
00:01:14 - Tall Chicks, Kinks, & Awkward Hook-ups
00:07:56 - Kill Tony: Kill Or Be Killed
00:13:14 - Favorite Dating App
00:19:19 - Contrarian Dating History
00:30:02 - How To Pick Up A Woman
00:40:05 - Kyle's Instagram Impressions
00:48:53 - Elon Musk
00:52:59 - Tony Robbins Birthday
00:55:59 - Tony Big Words
01:00:31 - Bombing At Private Events
01:10:05 - Always Working
01:12:47 - Kyle Wants To Be Adopted
01:16:51 - Wrap Up

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1h 20min

FAQs about 2 Bears, 1 Cave with Tom Segura & Bert Kreischer:

How many episodes does 2 Bears, 1 Cave with Tom Segura & Bert Kreischer have?

The podcast currently has 301 episodes available.

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