Caleb Pressley | This Past Weekend w/ Theo Von

Caleb Pressley joins Theo for the second time on This Past Weekend. They talk about life on the road with Barstool Sports, why cult leaders aren’t that bad, and what else happened during his interview with Aaron Rodgers.
bit.ly/theo-von
Caleb Pressley is a contributor for Barstool Sports and hosts the show “Sundae Conversation”. He was formerly a QB and Supervisor of Morale at UNC.
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[@TheoVon]

Caleb Pressley’s Wild Day w/ Aaron Rodgers kzbin.info/www/bejne/in6UYp2cq8SpkLM

[@skylargardner5351]

Please bring Caleb on as your co-host and take over the internet!!! Love y'all's chemistry, been upstairs from the intro. Thanks for being you Theo, your comedic genius is far too under appreciated

[@aaronl6333]

The Original Hooters is actually in Clearwater not Tampa

[@MrBuketman]

That trans looks like a damn cartoon! 😂 You can’t tell me that is casual. And around kids?? Lmao

[@towtrucktom1458]

"HERPES AND SLURPEES"

[@SmedleyButlerIII]

I'm pretty sure Aaron Rodgers on This Past Weekend... would be the greatest 2 hours of a lifetime 🤘

[@jasminerice00]

After losing my father, taking care of him in our make-shift "hospital" bedroom, my cat passing that was 16 years old that I witnessed born, and being blindsided by my ex breaking up with me after an 11-year relationship all within less than six months, bingeing this podcast is the only thing keeping my face out of drowning water, barely keeping me afloat. Thank you, Theo

[@olly7066]

Stay strong lad

[@JP-kc3zx]

Be strong it will get better

[@autumnmount9747]

Keep strong! In 2020 I lost my dad, both my senior cats, and a few very close family members. That is when I threw myself into the podcast world for the first time. I found Theo and it seemed like he was speaking to my soul in so many of the solo episodes. When he gets real and talks deep emotions it makes me feel so much less alone. As uncle Joey tells us every morning on fb, much love!!

[@grahamgibbins8071]

Lost my Dad aswell 2 months ago. Youre not alone when feeling sad Jasmine. Sending Love and hugs wherever you are In the world. X

[@grahamgibbins8071]

@@olly7066 lad? 🤪 whoopsie

[@shooty22]

"He embodies woman, man and child in one" is by far the most accurate description of jared Leto I ever heard lmao

[@angeloreyes707]

lmao yes

[@boatsanhs9709]

“Does that make sense?” “Yeah. I don’t know why, but it does” Perfect way to explain Theo

[@ironwrit]

“Always looks like he’s at a wedding” lol

[@sensibilities1]

And that he’s always at a wedding 😂

[@jetlife2thenextlife371]

His metaphor game is top tier lol

[@oracrest]

I love how these two could join forces to form a complete beard.

[@brayden3822]

a van dyke maybe

[@billyhawk1]

Epic take😅

[@Artsoulkojostudio]

very underrated comment😂😂😂😂

[@shauncry9310]

They could join faces and form a full bead

[@checko561]

Disgusting how underrated this comment is.

[@jacobhanson8432]

"We had this guy on here that had some sort of disease where you can't talk... hmmm... a stutter he had a stutter" 😂 Caleb wanted to lose it.

[@usdjxavi]

Read this comment right as he said it 😂

[@7ocar]

Timestamp it! 🔈🔉🔉🔊🔊🔊

[@staririe]

@@7ocar 18:13

[@88killage88]

1:17:00

[@clgreen7]

Theo: “I don’t like bats” Caleb: “I tell you what movie you won’t like, Batman. It’s very bat-centric” 😂

[@PartiallyC0rrect]

That one and “He had that disease where he couldn’t talk… a stutter”

[@garrettdean7412]

I love Theo but Caleb is always coming up w these one liners 😭

[@TWHowl]

You know a movie you’d hate? Batman. Huh. Never seen it 😂

[@mushje]

@@TWHowl He got him there, He did the leg cross and put his hands down like damn! I have seen batman! But no I haven't. I've heard theo talk about Batman but never less you take his shit with a grain of salt. He just says random shit but its comedy not true.

[@TWOhype23]

“If one of those bounced into the street, a kid would go get it dude” - Theo talking about huge tits 💀

[@jasewilts6667]

A Theo and Caleb weekly podcast would go crazy

[@josevazquez1933]

This is what we need !! That would be insane. Two best out right now.

[@dylansmith3022]

King and the sundae

[@ivywoodxrecords]

Dude they fucking should

[@mynamesjeff347]

@@dylansmith3022 come on bro The Sundae Sting

[@alifelesstoxic1253]

Yaaaasss Please 🙏

[@ThumbsUps1]

when Theo called stuttering a disease 18:16 and caleb laughed, golden

[@noahblackwell2068]

This duo is iconic . And you can tell Theo really had a good time with this one these guys were meant to be friends.

[@mikehicks83]

Literally, 2 aliens! Lol 2 of the most unique guys on our planet, and we’re blessed to have both of them.

[@parkercoe3727]

@@mikehicks83 they seem cool but wtf

[@mikehicks83]

@@parkercoe3727 what are you “wtf-ing”???

[@landonian1223]

I think they already are! I saw a fun video where they were at the University of Tennessee football game together on the sidelines with the team. They got the coach with the jug of ice water after the win.

[@Pr3st0ne]

They match each other's energy so well.

[@TheCorneliusRambo]

“probably bidens doin it” in response to kardashians cutting their asses off got me dying 😂

[@draxemsklountz1942]

Lmaooo bro as he said if I read this and it made it even funnier 😂😂

[@Secretdawg925]

Bro me too

[@dylanlhotak7522]

Bro so fuckin funny I can’t 🤣🤣😂

[@_jdgeorge_]

Same with its probly Biden doing the Trans big tiddy story

[@jimtaggert7268]

Classic…the silence was 😂

[@elleblue]

"He kind of embodies woman, man and child all in one... he seems like he's always in a wedding"... this made me cry laughing

[@mikebradlydavis]

I like how Caleb stays on Theo’s ridiculous thought trail, they kind of both remove themselves from reality the whole time lol.

[@Not2Shoddy]

“He has like a disease or something where you can’t talk… umm… he had a stutter” Caleb: *breaks*

[@DA-lk5np]

so funny

[@DANGMOE]

"it could've flared up later, I don't know" omg hahaha

[@michaelclay-lowkey0215]

Okay n ooooooo

[@ngawarijacobs4019]

time stamp?

[@appoloumang]

​@@ngawarijacobs4019 18:10

[@gordy7006]

59:40 Caleb: "This is just me being completely transparent and honest" Theo: "Thanks" Best part

[@motogem1408]

🤣🤣 I caught that and laughed. Because he was so sincere🤣

[@tylermason9353]

Laughed at that too 😂

[@gummie20]

the abrubt change of conversation and comedic timing made it perfect

[@cerberus3426]

I have a feeling Caleb is actually super smart, looks like he's analyzing everything being said to hit with a good line. All while Theo is just natural instinct with his one liners.

[@damionjaquez7895]

fr 😂

[@stanvans3214]

Caleb was a walk-on QB at UNC, and went on to become the world's only "Supervisor of Morale."

[@tykeboy16]

He's obviously smart

[@UniverseWillProvide]

Caleb is the smart guy who thinks he can top the funny guy

[@cerberus3426]

@E. Cort you're a angry individual, get a job bro.

[@XxFunkMachinexX]

Dude the bit about Theo calling a stutter a " disease where you can't talk" was so goddamn funny

[@jakekilgore4791]

"They found a not alive body behind the machines" the most theo von thing I've ever heard

[@joshpickup2581]

A weekly podcast with these two would take over. They are the perfect match.

[@madskrillz2]

Only person that would be better is Riff Raff.

[@stevensantiago746]

@@madskrillz2 the Theo Caleb Riff Raff Podcast

[@nickfruge5639]

NOW WE’RE TALKIN I would be a regular at that pad

[@claytonchaos578]

@@stevensantiago746 that would be killer!

[@turbodude]

what do ya know, theo just ended his podcast with brandon schwab. maybe they will?

[@stonedpigeon]

Theo is someone who can make you smile just by talking random stuff, even when you're sad af

[@SingleMaltBuckeye]

Bc he's generally in a sad introspective state of mind.

[@ProtectoroftheRealm]

Caleb is a liberal rat.

[@pushin7402]

Love yo name man

[@riikyramirez6547]

Check out Caleb too he cracks me up

[@conjoy2102]

FrFr

[@YukiTenpoin1]

"Two white guys, one of em wasn't white"

[@yonabon]

Killed me

[@NicoSportscards]

Theo has officially met his match.

[@hammurds]

Riff Raff and Nick Swardson are also great

[@codyjemison9558]

@@hammurds came here to mention Riff Raff. You beat me to it

[@michaelford1056]

Spent the last 4-5 days binging Caleb and Theo then get blessed with this hitter.

[@hamman953]

Me too, literally watched the theo and caleb interview today thinking he should be on theos pod. Would love to see Andrew Callaghan from Channel 5 on here too

[@Shane-fq5bh]

Me as well

[@danielcooper7586]

Right!?!? I just watched all Caleb’s stuff in the last few days! How serendipitous 💯

[@danielcooper7586]

Right!?!? I just watched all Caleb’s stuff in the last few days! How serendipitous 💯

[@jdaddy9139]

That’s god baby!

[@bobhs1605]

Caleb, Theo and Riff Raff-let’s do it. The king, the thing and the bling

[@kaat776]

It would be MAGIC!!!

[@itsajoeybeat]

Man that would be lit. Upvote this lol

[@Goofmaxxin]

😂 💯

[@Obijuankenobiii]

Bobby agrees

[@BrooklynboyO2]

that would be an amazing episode if not entire podcast

[@RyanWilson-hj5ki]

They seem like they were destined to be best friends

[@koolaid2koolboyy]

Did Theo just forget the name of the band Led Zeppelin but remembers Letos band (which I just found out was letos) thirty seconds to mars? 😭😂

[@spfadden082711]

I think he does that stuff on purpose. I bet he thinks it all out

[@quinnck]

Two of the truly great personalities of our generation.

[@kensteel9872]

Excellent comment my good man

[@bmac215philly]

So true. 2 unique dudes that are hysterical

[@JustinR941]

That you know of.

[@scotthartwig668]

They’re definitely in different generations lol

[@gnarrokomotis1914]

They are good.....but easy buddy

[@sockdong1544]

I love whenever Caleb realizes that his joke has gone over theos head

[@rebeccahatfield405]

Nothing goes over Theo’s head !

[@elite6642]

Theo's laugh is so contagious. my face is sore from laughing so damn much. They need to do a podcast once a month at least, they were so funny together. Felt like when i get in a room with my best friend and we just start cracking the dumbest jokes off to make the other die of laughing.

[@gay4pay882]

Liar

[@elite6642]

@@gay4pay882 if you think I’m making that up then you must really be lonely.

[@Aweebittyfan]

He knows your lying ‘cause he has successfully disguised himself as a lamp for 2 weeks in your living room

[@colleenann772]

I laughed so hard, 😂😂😂

[@Myincrediblefriends]

Theo says things that people are afraid to say, but is also just nothing but receptive when someone else tells him about shit. He’s a relatable, always improving being. I think that’s why he does so well lol

[@Notdickcheney]

Lmao Theo saying it’s cool to be a cult leader then describes 3 guys that don’t lead cults got me and Caleb simultaneously laughing

[@49ERSoverEVERYBODY]

These two should have a podcast together it would hands down be the best pod in the game

[@freddie_mvp]

Barstool should capitalise on it now that they live in the same city.

[@heavendog3194]

@@freddie_mvp they would be asking them to give up their own show that they already run, tho.

[@freddie_mvp]

@@heavendog3194 you sure about that? Plus Theo has already bailed out from the King and the Sting.

[@inkandivy1794]

Watching theo laughing and cracking jokes makes everything feel ok with the world again.. life is good if theo is good ❤

[@katiemiller1523]

“I can drink water, I can eat salt… why can’t I drink salt water” lmao

[@adammanning1237]

These guys need their own show. Their energy matches so well

[@woodcouleecattle]

“If one of those bounced onto the streets a kid would go get it” Theo kills me 😂

[@Quiksilversurf311]

😂😂

[@nckfrmthapnw]

Shit got me too.. lol 🤣

[@owenschuessler8040]

I love when Caleb is in character during the sunday conversations but he seems like a super chill funny guy

[@andrewkerridge2565]

I like the Caleb Theo combo. I feel like Caleb’s chill nature lets theo feel at ease when he’s searching for ideas n stuff in his mind. It’s beautiful

[@agtcodybanks]

Caleb is such a funny dude, I wish he popped up on more podcasts. The Theo x Caleb chemistry is top tier though.

[@snoop-spencer]

I couldn’t agree with you more. Did you know that chickens don’t really lay eggs? They actual poop seeds and the eggs grow from the soil. It’s crazy.

[@yckit5263]

@@snoop-spencer R57RTOY

[@dgh4918]

It really is

[@reinforcedpenisstem]

He's not that funny at all. He just talks.

[@dianabunch8616]

This guy may get Theo’s comedic mind more then any guest that I’ve seen. Great episode!

[@joshpickup2581]

Caleb is the only person I've ever seen with the same sense of humour. They are so weird

[@jaypers232]

Go watch his Sundae Conversations

[@jacksontrollinger876]

it's cause theyre both intellectuals who pretend to be stupid, like Conan, who literally graduated from Harvard.

[@kingwild772]

@@jacksontrollinger876 spot on

[@twkrider1]

Caleb and riff Raff are the only ones I’ve seen that get Theo lmao

[@jelguwop299]

They are so funny i cant even tell when they’re serious

[@thatjack4]

Spoiler all his podcasts are jokes lol

[@JoeJoe-ri4bv]

@@thatjack4 it’s a mix of jokes and raw life advice

[@barrygaler3701]

8:34 "i was on a email chain with him that i should have not been of" lmaoooooooo

[@theembodies727]

Whenever Theo says “you know what I’m talkin’ bout?” I actually don’t half the time, but I’m always 100% on board.

[@CrimeForCrime]

Neither does he so it’s all good

[@ChrisAinsleyMedia]

When two comedic styles match perfectly. This was just a simmering hilarious chat all the way through. Can't help but smile watching them talk! 😂

[@steveperry7761]

These two guys have some of the best chemistry I could listen to them all day long they play off each other so well

[@Love_dakota_payne]

These two compliment each other’s comedy so well

[@LowkeyStoned]

It's actually kinda crazy how well 😂

[@CezaMVO]

I'm glad theo got to spend sometime with his cousin. Their comedy style is a perfect match.

[@zzsaul8075]

Waatttt????

[@fightclubdurden]

They're cousins?

[@andrewgriffin9244]

And brother in law

[@Kinobambino]

Thought they were just the same person from different dimensions

[@xCradleKingx]

They definitely aren’t related 😂

[@PaletteBegonia]

Il never forget that video of Caleb completely breaking character with somthing Theo said , over on his channel. Don’t matter how good you are at retaining those feelings..😂 Theo will break you down into laughter . Love these guys energy , y’all should work more together .

[@vHighSamurai]

PLEASE start a podcast together!!! I need this every week

[@MrHockeymonster17]

This needs to be a monthly podcast. One of the best duos ever

[@TheMattycizzle]

Hands down one of my favorite episodes ever. I legit was laughing almost the whole time. These guys together are perfect entertainment

[@yubs4892]

I can't tell you how excited I am to watch this as two of my favorite dudes are chattin it up. Frequent viewer of both of you guys. Keep it up. THEO VON. Had to edit the post just to add that last bit.

[@YouTubeMemester]

“He had a disease where he couldn’t talk …. He had a stutter!” 😂😂😂😂😂😂 bro

[@user-ht7mn2sy8e]

Great chemistry with these two. Couldn’t stop smiling

[@hausmell]

WHY is this the best podcast I’ve ever heard

[@jacquikirby9903]

Major crush on both these guys ❤❤❤ both so intelligent, witty and funny. Both their voices 👌🏼 so easy to listen to, love Caleb’s laugh ❤️ Theo’s one liners 😂

[@beaubostick6935]

Theo slowly bringing the southern accent out of Caleb has me dying 😂

[@Atm8y]

Caleb is very underrated. I’m glad Theo brings him on from time to time. W Caleb. Gang Gang

[@ReckTv]

Bro I can listen to these two all day 😂😂 Great podcast!! We need more Theo and Caleb collabs in the future!

[@matthewwells8561]

I got yelled at because I watched this while my wife was sleeping and I couldn’t stop laughing so hard the bed was moving. Well done.

[@juice1306]

It’s always an amazing day when Theo drops a new podcast episode

[@petRhastQeug]

Caleb is such a funny dude, great chemistry between him and theo too

[@erikhoryza9068]

16:25 is the best Theo quote about another person I've ever heard lmao. He means it so respectfully too 😂

[@kimmita2thirty2]

I love the pure giggle fest that is these 2 when they get together on a pod. Good stuff.

[@peytonbanks197]

“I don’t know why, but it did make sense” is how I feel 99% of the time listening to theos jokes haha

[@bdoginit]

I LOVE this duo. Been waiting for this since the last Caleb episode. He genuinely appreciates Theo’s humor and you can tell.

[@mandyhaacke2957]

This needs to be a regular podcast. Theo and Caleb are the best! Plus Caleb is so dang cute! Theo is too but Caleb has the wallen vibe and I dig it.

[@pacifictrapster9348]

These guys comical chemistry is through the roof. Just two funny guys shooting the shit. 😂

[@TotallyNoCat]

Caleb is a certified legend

[@bbcchhaapp]

I read your username and then saw the picture. Had me in tears laughing 🤣

[@nickmason2345]

@@bbcchhaapp dying😂😂

[@closinginonclosure]

A certified doinker too 27:35 "Jit Zitsu" says the guy who claims he's a martial arts and MMA fan and literally works for Barstool Sports and doesn't know what Jiu Jitsu is. 😂

[@KM-ts6co]

Certified killer. I fucks wit him

[@Bo-dr5wd]

Needed this today, taking my first step to sobriety in a few hours, so scared and excited at the same time, love you Theo! Out here doing Gods work! Gang gang!

[@cloudbloom]

Good luck brother

[@itsajoeybeat]

In a few hours? Lol were you fucked up at the time of commenting this?

[@joshuarohrer3261]

You can do it. I’m a little over two yrs sober. It’s hard to start, but trust me it gets easier.

[@jmoney7289]

@@itsajoeybeat lol yes and lol support the homie

[@jmoney7289]

We're coming back here for the update too dawg don't worry about that however focus on yourself

[@ATOGMILSIM]

I love seeing the growth of people like Caleb and Theo after the leave places like New York and los angeles

[@madoffsbuttbuddy7106]

Billy Graham the evangelist, myPillow CEO Mike Lindell, and the XFL guy: Theo's top 3 occultist practitioners

[@jasongunnel9465]

It was Crazy seeing these 2 giving Coach Heupel a Gatorade shower at the Tennessee Game!! GBO

[@6sheamus]

The chemistry between them both is insane. Great to hear Caleb's drawl a bit

[@danielmaloney946]

Music intro and exit is so much louder than the conversation that it woke my dog up twice.

[@fdsajkl70]

Dude ur SCOTT Stap video/Creed was amazing. So heartfelt and real.

[@laytonperry364]

This episode reminded me of sitting on top of a mountain overlooking my tiny tiny town and just having random conversations and laughing at just nothing and talking with my best friend

[@matthewwillis-lawrence3798]

Also shout out for all the newer Theo fans that made his page crack 1 million followers. Glad y’all are here to enjoy this masterpiece of a man

[@Cram_pie]

bro i just saw that! he has more than flagrant! holy shit

[@Nicolas111]

True 🙏🏽

[@iandanger883]

"Also" is an adverb that means in addition to. Starting a paragraph that way makes you sound dumb. Also, stop acting like you didn't just find out about Theo.

[@weretheelliotts9734]

So entertaining watching them try to out weird each other lol there both wayyyy too good at it 😂

[@bobbywinston116]

The perfect duo...and it could get even better when caleb is in character

[@daniellewebb7697]

These two together gives me pure joy

[@trel9388]

sup danielle

[@oIDomiNatioNz]

@@trel9388 sup tre

[@daniellewebb7697]

@@oIDomiNatioNz sup kack

[@daniellewebb7697]

*kek

[@trel9388]

@@daniellewebb7697 have a blessed day queen alhamdulillah

[@Nuck82]

I saw a survey of who Theo should co-host a show with now, they didn't have Caleb as an option but I picked other and wrote him in. Because these 2 together is just so good and would be different then most other co-hosting shows

[@joshprout1726]

Just lost everything here in Cape Coral due to hurricane Ian. This episode relieved a lot of stress! Thank you Theo & Caleb

[@BrayMusic317]

Sorry to hear that man. I live in Fort myers and the stuff I've seen is crazy.

[@joshuaeuhus9128]

Come to City First Church in Cape Coral at 1 PM for a distribution!

[@GyzelE]

@@joshuaeuhus9128 really cool of you to shout-out info like that

[@benparo171]

This is the most wholesome shit i have ever seen in KZbin comments, hope you’re all doing alright.

[@Bucknastyy]

Stop lying. It wasn’t that bad of a hurricane

[@WhiteGurlMagic]

The two of them cracking up at TransAmah Anderson had me legit giggling along with them

[@steph7960]

Could listen to these two for hours. Fantastic energy between them. Great to see it a regular thing.

[@MericaUnited]

“Theo Von!” I was hoping he’d open it like that 🤣

[@randistrickler2532]

I definitely wish sundae conversations were longer. 😂 it is the funniest stuff I've seen in a long time! I binged the hell out of those!

[@chambo9212]

I love how Theo talks about a stutter like it’s some kind of rash 😂

[@hellens4936]

Both of their personalities go so well, we need another one

[@theplourde]

Came here from a Instagram clip about that one teacher…this podcast didn’t disappoint. I’m also not allowed to listen to it at work for how much I laughed out loud. Worth it

[@timo4938]

What that man is doing is disgusting. Not to mention breasts that big are disgusting even on a female.

[@ChiliPeppers246484]

This needs to be a weekly pod. The shop teacher talk was goddamn hilarious.

[@Stwo]

I could listen to these two dudes talk about the news of the world for two hours every week. Sign me up.

[@Sogonrei]

I am a not really a football fan, I played on teams and love basketball, and love hiking and being outdoors but I knew Theo would make it fun and Caleb was down to earth and I was fascinated with the stories he shared about people he met, and some Theo and him had in common. The woodworking teacher had me in stitches with the two of you narrating. Thank you for a great and silly goose time once again our friend. ☺ Gang love Gang! May all of you have a good week! 🌞

[@OnlyFuns88]

Laughed the entire way through, played off of each other perfectly. Perfect cap to my night. Appreciate the content Theo, we need you. God bless brother.

[@poindexter9404]

I’ve never seen two broadcasters have such good chemistry. These guys gotta do more stuff together

[@CopReacts]

Theo's storytelling is simply unmatched.

[@aaronmartin4611]

I'm not much of a podcast guy, other than the Always Sunny podcast...but Theo is awesome lol Love it. Caleb, you're too funny lol You guys had my stomach hurting lol Comedy Gold

[@anderscrouse]

This is genuinely the first time I’ve ever said this about anybody, you guys genuinely need a podcast together I have no attention span and I just watched this one for 2 hours straight no stops. So Fucking good

[@bar3lyalive769]

Theo is literally the only person who's Ad's I won't skip because they're equally fckin hilarious.

[@adamtotten2052]

Joey Diaz’s are good too!

[@WalkingPaceWP]

someone never watched cumtown. the only podcast with funny ads

[@bar3lyalive769]

@@WalkingPaceWP Solid opinion there...thanks for the input sir.

[@dylancampbell52203]

What they said about anxiety is so spot on. I feel like people think it’s trendy or cool to have anxiety or depression and they just throw those words around when really all they’re feeling is a little stress. And then it lessens the actual experiences people who actually suffer from anxiety and depression go through.

[@BrokeMalone]

yeah but u could literally say the same for anything lol… like how kids overuse the word cringe for every situation on the internet, even tho its not making them physically feel awkward

[@drewweltin89]

Caleb sure seems like a great dude.