Name: Bert Kreischer Went Sky Diving With Rachael Ray | David Letterman
Uploaded: 2025-07-15T15:00:47.000Z
Description: Watch the stand-up comedy video 'Bert Kreischer Went Sky Diving With Rachael Ray | David Letterman' from Letterman on Comedy Buff. Published 2025-07-15. Transcript available.

Watch the stand-up comedy video 'Bert Kreischer Went Sky Diving With Rachael Ray | David Letterman' from Letterman on Comedy Buff. Published 2025-07-15. Transcript available.

Good to have you here.
Oh, it is great to be here.
Really?
Yeah.
Tell us about Burt the Conqueror.
It's an odd idea for a show, but doing very well, isn't it?
Yeah, yeah, yeah.
I'm a tour guide for thrills.
If there is something kind of crazy, dangerous, exciting, not legal, I'm doing
it.
Have you ever said no to something?
Yeah, but I ended up doing it anyway.
No doesn't go very far.
Give people who may not have seen the program the kind of thing that you do.
Give them an idea.
Okay, I jumped off the stratosphere last year.
That looked crazy to me.
Yeah, yeah, yeah.
That was up all night throwing up in a bathtub the night before.
I called my wife and I was like, I'm backing out.
I'm saying no.
I'm going to actually rent a car and run away.
What kind of insurance do you have?
I don't know, Dave.
I'd look into it, Burt.
I don't know.
I don't know if it's my insurance or theirs.
That's a really good question.
Iron that one out.
Yeah.
And then I saw you at a backyard slingshot party.
Oh, this was the most dangerous, unregulated thing I've ever done.
It's a backyard slingshot.
So it's two huge telephone poles with bungee cords over top of them.
And they're like 100 feet up.
Then they throw a rope up, pull it down, harness you in,
and then sit you on the back of an ATV.
And you hold on.
That's right.
And they just take off.
And when you can't hold on anymore, you slingshot, like, 70 miles per hour into
a canyon, just back and forth.
Just, huh?
And when I did it, I told them, they were like, how much do you weigh?
I was like, why are we checking this out now?
Yeah.
Kind of like that insurance question.
And I was like, 2, 230?
And then I was like, let's just say 240.
I don't know, like, 240?
And they're like, you may hit the ground.
And I was like, it's 70 miles an hour?
Well, it looks, I don't know anything about physics, but it looks like you're
going to go right into the ground.
You, I skimmed the ground.
I literally, my feet were like this, and my butt, my heels were scraping the
ground.
And there was a medic on set, and I was like, I was like, so what's the worst
that could happen?
He goes, you're probably going to break your back.
Yeah.
I was like.
Did somebody, now I've seen also a lot of amusement park rides.
Yeah.
Those are safe.
Yeah, those seem safe.
This kind of seemed like a bunch of guys drinking a lot of beer.
They're Mormon.
They're Mormon.
They didn't drink any beer, which makes it even scarier.
Yeah.
Like, if you see a six-pack next to the guy that built that, you're like, okay,
let's try it.
Yeah, we're in business.
But did somebody test ride the slingshot before you get in?
Yeah, a lighter person did.
Yeah.
But the thing that, it was interesting to me, they had no problems putting
their kids in this thing.
Yeah.
So they'd be like a nine-year-old little girl flying off through this slingshot.
And like you said, they're going 70 miles an hour.
They're going 70 miles an hour.
They're putting their children on there and just rocketing them.
Back and forth.
Right.
But they're so light that they're up like 20 feet above the ground.
Sure, yeah.
And then old Fat Boy comes in and I do it and it was sketchy.
Yeah.
And then, you know, TV is all like, they're like, well, we got to do it again
just to make sure we get the shot.
And I was like, no, no.
No, no, no.
We got the shot.
Let's not roll the dice.
We got it.
But again, going back to my point here, in any other circumstance, this little
operation, with or without you, would have been shut down.
And hands down, no questions asked.
And our producers see gold.
They're like, oh, this will be great.
If he breaks his back, can you imagine the press we'll get?
And how long have you been doing this show?
I've been doing this show.
This is my second season.
I just wrapped.
I'm safe.
I am healthy.
All right.
What kind of things did you do this season?
This season, we went shovel racing.
Have you ever done that?
Shovel racing?
Shovel racing?
I don't know what that is.
You just sit on a shovel.
That doesn't seem like that much fun.
It's scary.
You sit on a shovel at the top of a mountain, and you just go down a mountain
at like 70 miles an hour with a stick just...
Sorry.
No, I'm just saying...
I know.
Now, what you haven't said here is snow?
No, there's snow.
There's snow.
There's snow.
Yeah, yeah, yeah, yeah, yeah.
Yeah.
It's very safe without snow.
You don't go anywhere.
He just was thinking there's not much happening.
With the snow, you get cooking.
You just fly.
Where did you do that?
I did that in New Mexico.
And then I did bungee jumping.
I went skydiving with Rachel Ray.
I did...
Wait a minute.
What?
Rachel Ray?
Why?
She's a gangster.
Like, she's so pimp.
She, I go to do her show, and then I say, she goes, what's one thing you'll
never do?
Never, never, never do?
And I go, skydiving.
I'll never do it, because the numbers are really high for deaths.
Like, they're, like, uncomfortably high.
Like, you know, like, if you get four or five, you're like, oh, I've seen those
on TV.
But, like, when you get to, like, 32, you're like, 32?
And so she goes, I go, skydiving, and she goes, well, would you go with me?
And then I'm thinking, ratings, that'd be great, right?
I'm like, yeah, yeah, yeah, I'll go with you in a heartbeat.
I'll do anything with you.
You're hot.
So, uh, and she can make a meal in under 30 minutes.
And if you take her on a date, she's not spending more than 40 bucks.
That's right.
So she is like a home run.
Yeah, home run, exactly.
So then we went skydiving.
She goes, all right, let's do it for my show.
And I was like, oh, man, I got, I didn't get the ratings on that.
And then, and then we went skydiving.
That was terrifying.
How, what altitude did you jump?
I have no idea.
Hot, uh, I don't know.
I couldn't listen to electronics.
Was there a guy on your back?
Yeah.
Yeah.
It's very emasculating.
Yeah.
Like, to just be sitting in a dude's lap and him just holding you.
Yeah.
And, and, and you're trembling, like nervous, like, and he's like, calm down.
This is going to take a second.
It's going to happen so fast.
Yeah.
You're not going to feel a thing.
And, and it's very, like, it was, it was very, and then my guy, my guy was
German, or
he looked German.
I don't know.
I wasn't listening much.
He looked German.
And he told me, he goes, he goes, you couldn't kill us if you tried.
Really?
And I was like, in my head, part of me is like, I bet I could kill us.
He's like, but, and then he's like, you couldn't.
And I was thinking, I could totally kill us.
How, how long after you landed did he remain strapped to your back?
Because that's, that's the key.
If you find you're having lunch, then something has gone wrong.
Honey, I want you to meet Sven.
Bert the Conqueror, a whole new season.
And how many years do you think he'll do this?
I think I'm done.
Yeah.
Wednesday nights at 10 p.m. on the Travel Channel.
Thank you.
Nice to see you.
Good luck to you.
Thank you.
Good luck to you.