Do you remember some of the early challenges
that stick in your mind that were just like-
Oh yeah, God, there's so many.
Well, my favorite is the Trojan horse.
Yeah.
Whoa, what was that?
First of all, we had no budget.
We had no freaking money back then.
So they wanted this huge Trojan horse
to hide all our writers in left outside
of Letterman's stage door.
(Jessie laughs)
Right, Is it comedy bit?
Conan's gonna send over writers to Letterman.
We were gonna take over the letters.
They were supposed to infiltrate his show and-
who wrote it?
Brian Rich wrote it
But you were in charge of everything.
I shot the whole thing
and we had to shoot it and edit it the same day.
Well, we didn't have a budget
to build that thing.
So I had two friends
of mine in New Jersey, build it in our driveway.
Wait, seriously?
So it didn't have a studio, a shop, a stamp on it.
Everything we did at the beginning
of our show was illegal.
(Jessie And Mike Laugh)
I think there's a statute of limitation
Right, I think we're safe.
We broke every rule you could possibly break,
union or building.
I love this.
And I'm not kidding.
I believe you.
We used to never get permits
to shoot any, we would just go out and shoot.
When we did the Trojan horse,
we had an 18-wheel dump truck
that once the horse was left there
we ran through it with the dump truck.
Right. And smashed it.
(Jessie laughing)
We backed up.
We backed up, I was sitting shotgun.
We backed up to Eighth Avenue
and we're getting ready to go
and I look ahead of me
and Adio had not cleared 53rd street.
Oh.
Jeff Adio was the production coordinator
at the time.
Yeah, and there was a wall
of people right in front of where we were going.
Just to set the picture.
The first of all this Trojan horse,
can you describe how lar,
you said friends built it in a driveway
that blows my mind
because can you describe how huge it was?
It was about 18 feet high
and about 16 to 20 feet long.
Oh, wow.
All on wheels
and there was a door inside one of the legs
where all the writers got in.
Before the truck hit 'em.
Yeah, it was a functioning Trojan horse.
Was there a bathroom?
No, there was a kitchen.
Yeah, a Kitchenette.
(Jessie laughing)
The whole idea was we send it
from our studio which was only three blocks away
from Letterman's studio, which is now Colbert's studio
the old Ed Sullivan Theater.
Right. So we pushed it
across seventh avenue, down 53rd
to the stage door entrance of the Letterman
Across seventh, across Broadway.
Right.
And so then the end of it was,
you mentioned this giant dump truck,
was gonna barrel down 53rd
and smash it to smithereens
Oh. Correct.
With the writers inside?
Yep. Yes.
They were actors.
so they were expendable.
(Jessie laughing)
So you're saying Jeff Adio,
the coordinator didn't, he didn't clear 53rd street.
There was a wall of people
from from corner to corner on 53rd.
It was like right in our path.
Yeah, 'cause they wanted to be on TV.
So what happened?
Well, I told the truck driver
to drive back up there.
So we drove back up.
I said, "Jeff, do you think we might wanna get rid
of these people?"
Which he did.
Okay, so they just yelled at 'em like,
if you don't move you may get run over by a dump truck.
Yeah right, exactly.
I remember Martin Scorsese was the guest
after that aired and he just went on and on.
He really liked it.
Oh, was he impressed with the directing?
No, but- Oh, yeah.
He just liked the bit, so that was sweet.
Yeah, so a lot of stuff was built illegal back then.
I didn't know that.
Oh shit, yeah. All of it.
Remember the catapults?
No
The catapults, they called
for a meeting in the conference room
on seven or nine,
whatever the hell floor we were on
after work on a Friday.
Okay.
On Monday morning, they wanted to have,
They wanted to somehow drop gummy worms
over the whole audience.
(Mike laughs)
So I'm sitting down at one end
of the table and Jeff Ross is up at the other end.
Our producer.
And I'm thinking in literally
in about three minutes, I calculated how
to build a catapult
that would throw gummy worms.
I went to New Jersey to our stage manager's house,
built it that weekend, dropped it off in the city
on my way back through to Long Island where I lived.
And then Monday morning we set it up
and when we let the catapult go
with the gummy worms on it.
Yeah.
They flew about eight feet
and landed on the floor in front of the house band.
(Mike and Jessie laughing)
So.
I was worried it was gonna go the other way
and be so powerful that they took someone's eye out.
That's what I was waiting for.
So I'm sitting there
and I said, "Don't worry about it",
which is just a couple of adjustments.
And I went back and I tightened
up the bungee cords to give it more power.
Yeah.
For the live show, they went back.
Uh oh.
Eight feet in front of the band again.
(Jessie and Mike laughing)
No change, no nothing.
And Conan stands up,
he puts both hands on the desk, leans over
and he goes,
"Let's hear it for the crappiest catapults on television"
(Jessie and Mike laughing)
Jersey built.
The next morning,
they wanted to do with this Bluebird of happiness.
A bit called the Bluebird of happiness ,okay.
Yeah, and it's supposed to fly in
and land on somebody's shoulder.
I think Mike Gordon.
Okay.
So they're all going, "Well, how we gonna do this?
How we gonna do this?"
And I, from the other end
of the table I go, "Well I got catapults."
(Mike and Jessie laughing)