You go to "Second City" and there you meet,
you hit the sweet spot because-
Tell me who's there when you're there.
Okay.
So the first show I saw at "Second City,"
I moved there in the summer of '95,
I just graduated college,
I didn't know what I wanted to do,
but I knew I wanted to go to a big city
that wasn't necessarily Atlanta.
You know,
I just wanted to see more of the country,
more the world.
I moved to Chicago.
So the summer of '95,
there was this crazy heat wave in Chicago,
and it killed people.
Like, 800 people died in Chicago that year.
Oh, God.
So here I am
with my cardboard suitcase.
(everyone laughing)
No one to blame but yourself now.
Gosh!
That train's up in the sky!
Okay, the elevated train in Chicago.
No, I get it.
So that was my first, you know,
taste of life in the big city.
And it was so hot
one of my roommates was saying like,
"Hey, you know what,
there's a comedy theater downtown.
They do free improv after their show,
cheap beer,
and it's air conditioned."
I was like, "Sold!"
So, I went to "Second City"
for one of their free improv sets,
and I'll never forget it.
That was like my, you know,
(imitating light bulb flickering on)
An "aha" moment, yeah.
Exactly, exactly.
So it would've been,
I think Adam McKay, John Glaser,
Kevin Dorff, Rachel Dratch,
Jenna Jolovitz,
and I think Scott Allman
were on stage then.
And so that's when I just fell in love.
And it really was one of those things
where I was like,
"This is what I do with my friends.
Just like, hanging out.
They're doing this for a job.
This whole audience is eating them up
with a spoon!"
And so I was like, "I wanna do this."
So, I signed up for the classes
and I would just keep going back to shows.
I would see Tina Fey,
who joined the main stage
taking the place of John Glaser.
Mm-hmm.
It was just so fun
to see the evolution of these things.
And for me, like the feather in my cap,
you know,
and of course going all through all that.
But from remembering that point in 1995
to working my way up
and then being able to work with Adam McKay,
and being able to work with John Glaser
and Rachel Dratch and Tina Fey
and Kevin Dorff,
and all these people
who like inspired me.
That's pretty cool.
It was fun and I do not take it for granted.
It's funny 'cause you mention all those people,
and I think there's-
I mean, obviously,
a couple that went to SNL
but there's so many people you mentioned there
that ended up being writers for me,
performers for me,
and just realizing, you know,
that that whole generation of comedic performers
were people that I got to work with.
And then you come to New York-
They were the bridge that got me to you.
Yeah.
You came to New York,
and you started doing stuff for us.
And then it was really fun
because for years you did bits for us.
Then you get cast in "30 Rock"
and you start coming on as a a celebrity,
which was, you know,
I mean, just wrong.
Wait, what?
(everyone laughs)
No, no,
it was really cool to see that happen for you.
It's no fun when I'm sincere.
God dammit, it's just not as funny.
I'll get the sincere shit out of the way,
but it was really nice to see you.
You were always a very talented
and funny, sweet guy,
and you did all this great work for us.
And then you became Jack McBrayer,
and we would have you on as Jack McBrayer,
and the crowd would be like,
"Oh my God, there he is."
Right?
When you didn't have to be dressed
as a mule or a spinning wheel or anything.
I just chose to.
Yeah, exactly.
(everyone laughing)
You still came on as a mule,
but that was your choice.
(Jack laughing)
But you come on,
and when Tina approached you
to play this page, Kenneth,
on the show on "30 Rock,"
did you look at the character
and just know exactly how to do it?
I did.
Which she kind of wrote to you.
She did.
And I don't think that's any secret at all,
but I knew Tina from Chicago "Second City" days.
Her husband, Jeff Richmond,
was my director at "Second City."
So I was definitely connected to them
and they knew my work.
So when it came time for her
to write the pilot for "30 Rock,"
they did add a page,
and I think it was written towards me.
I still had to audition and everything,
but man, I'm glad I got that.
How did you prepare for that?
Did you-
Well, I knew that script backwards and forwards,
because even though Tina
was really rooting for me,
you know,
I still had to prove myself to all the network,
the studio,
all that kind of thing.
So, I got prepared,
and I don't know if you know this story,
do y'all know the story about
when I put myself on tape
for the "30 Rock" audition?
Mm-hmm.
I happened to be in New York.
So this would've been the summer of 2005.
And I happened to be in New York,
I think for an improv festival.
Tina got wind that I was in town,
so she was like,
"Hey, I know you're in town.
Will you stop by the NBC casting people,
put yourself on tape
for the untitled Tina Fey pilot?"
And I was like, "Uh, yeah."
So, because I knew that she had like,
kind of tailored it towards me,
I needed to crush this.
I needed to knock it out of the park.
So besides being very prepared,
I was like,
"How can I make the best impression possible?
You know,
I've actually played a page
on Conan's Late Night Show multiple times.
I wonder if-"
So I called up y'all's page desk,
and I got up there
and I talked to wardrobe.
I was like,
"Can I borrow, just for 20 minutes,
a page uniform?"
They're like, "Yeah, whatever."
So they put me in there.
Your hair and your makeup people,
you know, gussied me up.
And I went upstairs to the whatever floor,
put myself on tape
for the untitled Tina Fey pilot
and that is the tape
that got me through the studio,
through the network.
It got me the job.
Is it fair for me to say you-
(everyone groaning at Conan)
You used my people!
Absolutely not.
You used my wardrobe!
You used my makeup!
Okay, and see,
this was supposed to be a nice story
and here you go,
here you go.
I'm sure I deserve some percentage.
I'm sure you don't.
Percentage?
(everyone laughing)
I did not know that.
I did not know
that you had stepped on my back
to reach this great height.
But yeah, yeah, whatever.
I'm used to it.
What else is new?
Because you play that part,
and I occasionally remember,
wait a minute,
I'm in the early "30 Rocks."
I completely forgot.
Yeah.
Because I remember Tina coming by
to shoot a part where
I think Tracy was on my show.
The episode was called, "Tracy does Conan."
The sixth episode of the first season.
Yeah.
I guess we used to go out
was the idea?
Correct.
I think I was Tina's,
Liz Lemon's old boyfriend.
Correct.
Y'all were supposed to
lose your virginity to each other.
Yes, yeah.
And then-
Which is very plausible.
And then I did a scene,
I remember I had a scene with Alec Baldwin
on the show once.
And that was just the very beginning of the show.
And then the show took off.
Yeah.
They did not need me anymore.
(everyone laughing)
You came back.
We made many references to you.
Yes.
I remember, I think Tim Conway's character-
Tim Conway makes a reference.
I know!
It was such a funny joke.
Tim Conway says,
"I saw Conan O'Brien
in the hallway with a guitar."
'Cause I used to just walk around "30 Rock"
with a guitar.
I always have a guitar around,
just a nervous habit.
So, I think Tim Conway's line was something like,
"I saw Conan O'Brien.
Who is she,
and why is she so sad?"
(everyone laughing)
Honestly, I think it was like,
"I saw a tall lesbian with a guitar.
Who is Conan, and why is she so sad?"
(everyone laughing)
Okay, better.
That's such a great-
"Saw a tall lesbian in the hallway."
Stupid.
But it makes me very happy.