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Jayson Cross

Chicago-based stand-up comedian Jayson Cross, guest host on the VentThis podcast and creator of the "Comaoke" comedy karaoke show.

Sep 15, 2026

3:01
Right
3:01
... around 12 or 13.
3:02
They got divorced, and then we moved to a neighborhood called Bronzeville in Chicago, which is, like, a very professional Black...
3:09
It's like a upper-mid, middle to upper middle class Black neighborhood, and we moved down there from 71st.
3:15
But, like, all my fondest memories were on 71st.
3:17
And then there was this gang in Chicago, huge gang, but they split into two.
3:23
But our neighborhood, you know, they were still cool.

1 HR 10 MINS LATER

73:10
Yeah
ChrisHOST
4:58
And Kyle's her good friend.
5:01
Wow.
5:03
Who is...
5:03
Well, I...
5:05
Well, the moral of me, of course, is like go and tell, but then there are social dynamics at play.
5:12
Who is she friends with first? Who does she have loyalty to? Because if she was friends with the girl first, maybe she should talk to the girl and say, hey, what the heck are you doing? You're engaged.
5:23
You're about to get married.

18 MINS LATER

ChrisHOST
23:20
Yeah.
ChrisHOST
3:16
Women are crazy.
3:19
No, women aren't crazy.
3:20
I have to say he's the crazy one in this situation.
3:24
You didn't get the hit the first time.
3:26
You should have watched the episode.
3:28
They were trying to introduce you into some sort of sex cult or some sort of sex group.
3:34
They do group sex all the time.

11 MINS LATER

ChrisHOST
14:08
Jason, what do you got?
ChrisHOST
12:06
He
12:06
tried to tell us.
12:08
Mr. Orwell tried to tell us many moons ago.
12:10
We didn't listen.
12:11
And now it's here.
12:13
We can't seem shocked.
12:14
Have you ever been speaking about something around your phone and the minute you open it up, there's ads for the things you were speaking about? Say you're speaking about pies.

8 MINS LATER

ChrisHOST
20:22
We're all waiting around.
ChrisHOST
1:21
So I mentioned earlier that the show's titled Airline Vents, and I wanted to ask Jason, because I know I have a few, but have you had one? Airline.
1:32
Are you kidding me? Hell yes.
1:34
My biggest airline event right now.
1:38
I hate that they upsell everything.
1:41
They upsell everything.
1:43
I think Spirit Airlines is defunct now.
1:47
Probably started the model.
ChrisHOST
6:21
I know.
ChrisHOST
12:49
And he'll pretend like it's blood and try to get sympathy from
12:53
people.
12:54
Can you imagine that? Oh, my God.
12:56
That's almost, yeah, no.
12:59
No opening ketchup and driving.
13:01
He should be pissed off.
13:05
But certain foods you can't eat while you drive.

9 MINS LATER

ChrisHOST
22:29
I think
ChrisHOST
1:25
So tell us a little bit about that article that happened, that was written about you that happened while you were in New York, right? Yes.
1:34
I used to live in New York and I would get my dry cleaning done in hell's kitchen.
1:39
One day I'm going to pick up my dry cleaning.
1:42
I see a gentleman with a brick.
1:44
I got defensive.
1:45
I thought he was going to hit me.
1:47
He said no, and then he used a semi-racial slur, I would say, and let me know that he was going to hit someone else.

6 MINS LATER

ChrisHOST
7:33
Wow.
ChrisHOST
10:29
All right.
10:29
Yeah.
10:29
If I'm gonna do it, why not do it? But I think the father's primary concern is, "What else can this girl get my son to do?" And they're probably growing apart, 'cause if he's in high school, he's probably spending less time with parents, more time with the girlfriend.
10:44
And he may have said, "Hey, son.
10:46
Why don't you try this, uh, quesadilla?" And the son was like, "No, I, I won't eat those." And now he's going to get his toenails painted, something that he probably would've never done before.
10:56
So the father may have a little bit of jealousy.
10:58
"How is this girl having more influence on my son than I did?"

8 MINS LATER

ChrisHOST
19:21
What do you think?
ChrisHOST
4:47
Yeah
4:48
... th- I went to a Catholic all-boys school, and there was a chess tournament.
4:52
Um, and I remember maybe ...
4:55
I, and I haven't, I didn't play previous to that.
4:57
I hadn't played chess, didn't know anything about it, and my mother suggested I get into the tournament.
5:02
And she went out and got one of those boards, you know, half chess, half checker boards.
5:07
And got a book.

18 MINS LATER

ChrisHOST
23:22
Uh-
15:50
So did it trigger then that, okay, this guy might be in trouble?
15:55
Not then even, 'cause I just thought the guy was a crazy coward just walking with a brick.
15:59
Not then even.
16:01
So the gentleman, the perp with the brick, he picked the brick up over his head the same way you would try to strike-- you would strike a nail with a hammer if you wanted to hit it with intense force.
16:16
So he picked it up over his right shoulder, over his head, and he struck the gentleman in the red burnt orange hood on the left side of his chin, and he went down like a ton of bricks.
16:28
So he kinda like, when he hit him with the br-struck him with the brick, he let it go.
16:33
It was almost like a downward throw/strike, if that makes sense.

17 MINS LATER

33:25
How did this affect you mentally?

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