Name: Theo and Caleb Pressley Talk About Going to Jail
Uploaded: 2025-05-14T19:00:15.000Z
Description: Watch the stand-up comedy video 'Theo and Caleb Pressley Talk About Going to Jail' from Theo Von Clips on Comedy Buff. Published 2025-05-14. Transcript available.

Watch the stand-up comedy video 'Theo and Caleb Pressley Talk About Going to Jail' from Theo Von Clips on Comedy Buff. Published 2025-05-14. Transcript available.

I want to know how these guys take so many photos while they're in jail.
Oh, dude, jail is like basically like being at a...
It's like an influencer trip.
It's like raising canes, take you to F1.
It's like basically like a Cinnamon Hampton Inn kind of.
It's gotten to be like...
Have you been in jail?
Yeah, I've only been in jail for one night, though.
You spent a whole night there?
Yeah.
What'd you do?
We sang at the beginning, but...
Because I was trying to fit in or whatever, and I like...
What about beforehand, before you went in there?
Oh, apparently giving drugs to kids.
Unreal.
What state?
Unreal.
First of all, Mississippi.
Bro, if you're going to get...
You're going to pop me for giving drugs to kids?
When everybody here is recovering from opioid addiction,
when they tested these syrups, they tested nine out of 40 syrups,
at IHOPs in Mississippi, tested positive for fentanyl.
And they're going to come at me.
That's unreal.
I'm just saying boo-boo kitten.
Did you get any good flicks while you're in there?
Chill out, huh?
No, what did we do, dude?
We sang.
There was a little bit of freestyle rapping.
And then prayer, personal prayer.
And that was it, man.
And then let me out.
Did you pull all-nighter?
Did you sleep?
Oh, no.
You don't sleep your first night.
That's a rookie move.
Too much to do.
Yeah, you just got to...
You can't be the guy that gets hit or press you like...
Oh, so you got to sharpening your knives.
I'm going to get a little bit of shut-eye.
Dude, no, you basically have to spend the first couple hours chaining your ass
to the wall.
It is...
Freedom is not freedom.
Yeah.
I mean, it's a lot in there.
It's a lot in there, man.
What about you?
Have you been?
I went for a...
We stormed a court in Connecticut at a UConn game.
Hell, yeah.
And they were upset that we didn't even get to storm it.
We were going to try to storm it.
But what was it about?
Was it because of that...
We're doing a storm change.
Women's lib or whatever.
Not the Roe versus Wade thing, huh?
No, it wasn't that one.
It was just a basketball game.
I think it's a ranked opponent.
Oh, you're talking about sports court?
Sports court.
Oh, yeah.
I thought you guys took on the judicial system.
Who do you think Roe versus Wade was, dude?
No, dude.
I thought you had the wrong sport.
Kind of did.
You thought Dwayne Wade versus somebody?
Dude, I know my court cases.
Don't say that.
Yeah, we got arrested.
I forgot about that.
But we just went to jail for a couple minutes.
Oh, yeah.
And when we came out of jail,
people were outside cheering for us.
Yeah.
Seriously.
It was like a movie.
We didn't even have it filmed,
but it was amazing.
Was it guys and girls in Mississippi jail?
Or just guys?
There was some men in there.
There was one...
I don't want to say there was one...
like a first-round pick.
You know what I'm saying?
Like a...
There was like a...
Bukers?
Huh?
Paige Bukers type?
No.
There was like...
There might have been a woman in there.
You know?
It's don't ask, don't tell in there, brother.
Too much other stuff to do.
Yeah, it's definitely...
Yeah, while I am like...
Begging people for burlap underwear in there.
Okay?
Like...
How do I get two of those spike strips
so I can put them around me...
and then...
I just need two spike strips
at the top of my underpants.
Like, hey, can you help me, officer?