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Okay, let's get started.
All right.
This is a special thing we're doing lately.
Normally, I would talk to a fan somewhere around the globe during this segment.
But these are different because I have my amazing Oscar writing team downstairs.
These are writers that are... They're the best.
They really are the best.
And I... hang out with them all the time.
We try and think of fun things we could do at the Oscars this year.
And since I have this room downstairs, I'm pilfering them one by one to talk to them and just find out more about them, because they're very funny, very talented.
And today it is Skylar Higley's turn.
Skylar, let's hear your origin story.
Where are you from?
Um...
Can I first say, this is the most respectful I've ever heard you speak to me.
Thank you, thank you.
That's what I said last time.
The Colin O'Brien, yeah, I love these writers.
Yes.
In 20 minutes, it's going to be different.
Let me say something.
Well, we should also say that anytime I enter the room where you guys are, the kind of dungeon No, it's a nice room, but I can't just walk into the room.
I kick the door open like it's a drug raid.
And then I come in and I start doing cartoonish over the top. insults I say you guys are the best writers I've ever seen this is what I was waiting for just now but then I realize I don't have my glasses oh okay so I go to put my glasses on and then I look at them again and I show cartoonish disappointment in what I'm seeing and it's it's all theater yep but I think I know I have a good time we have a great time And then we wait for you to leave and then we work.
Yeah, then you get back to work.
Oh, I can really tell when they're like, okay, he's done like 35 different riffs.
We've got to get him out of here so we can get back to work.
And you ruined the door downstairs.
I kind of did.
There are scuff marks on it every day.
Yeah.
I know, I know.
I love it.
I like it a lot.
It's a treat for me.
I just sit there and wait and go, hey, let's tire himself out.
But I don't.
I don't tire myself out.
Skylar, yes, tell me, I remember when you first started working for me, which would be, what year did you start working for me?
2020.
Okay, 2020.
Do you remember in the middle of the pandemic and there was the BLM?
Remember when we cared about BLM for a second?
Mm-hmm.
And it was right in that time.
I was like going really crazy because it was Chicago and the police and everything were there.
And then it was like I was having like just a lot of anxiety around that time.
And then people called me up and were like, hey, do you want to meet with Conan's people?
And just for like a meeting.
And I was like, yeah, I guess.
And then it was like, oh, yeah.
Do you want to write for a Conan O'Brien show?
And I was like.
Well, I think the world's ending.
So sure.
Like there was a virus.
There was like an uprising of social, you know, it was like, fine.
Yeah.
This will be the last thing I do.
But what I remember most is that, because everything you didn't move, because it's the height of, you know, not just COVID, but so much insanity.
So you would zoom in from your apartment.
Yeah.
And your apartment was in Chicago.
And I remember the angle was...
I don't know how much of it was the angle and how much of it was the apartment.
It wasn't the angle.
I lived underground.
Okay.
It looked like, so Skyler would, you know, okay, here's Skyler.
And you would appear on the screen and it looked like your ceiling was one inch above your head.
Yeah.
And it looked like you were being held captive.
It looks like in being John Malkovich when he has to go into John Malkovich's head and the ceiling's really low.
That's kind of where I live.
Yeah.
Yeah.
But it's cheap rent when you live underground.
Let me tell you something.
Well uh, I mean this has been much discussed, but you've done hilarious, hilarious work for me on the Conan show.
And then on the work you've done on the Oscars last year.
This year has been stupendous.
You wrote that insane joke last year.
It was one of my favorite jokes to get to deliver.
Oh, and it was also like...
Just I don't know.
It just sometimes in comedy you have that moment where things just like line up.
You know where you just get blessed with a premise and like this is a perfect, it lines up and you do it.
And I didn't you know, I don't know if anybody expected it to be quite as big as it was.
I think there was a sense before I went out.
Well, I thought, well, this will be fun.
Yeah.
Yeah.
And I don't want to misquote it.
So maybe you can um remind us.
Yeah, i walk back out.
It's the beginning of an act, beginning of the midway point, which is important because last year the super bowl, kendrick performed at halftime and then he did his stuff with kendrick and drake everybody remembers and you just come out and you say well, we're halfway through the show, so it's time for kendrick to come out and call drake a pedophile yeah, And so I tell that joke and then I'm just bathed in not just laughter but screams.
And I have to tell you, if you have a disease, if you have cancer in your body, and you walk out and tell a joke like that to a room that big and you get that reaction, you will be cancer free.
It cured me of any ailment I might've had, huge.
And then I walk right backstage and there you are all nicely dressed.
I think I gave you a thank you.
And then you were like, your name is Skylar, right?
I noticed the moment Conan started respecting me as a person.
Yeah.
Yeah.
Well, started to.
And then you spent that capital really quick.
Oh, of course.
But I'm curious.
I haven't really sat down and talked to you about your backstory.
When do you start thinking, OK, comedy is my thing.
This is what I'd like to do.
How early did you get the bug?
How did this all happen for Skylar Higley?
Um, i got the bug, you know early, like as kids, i feel like i, i was like, i feel isolated, i feel like a weirdo.
Uh, you know a thing or two about that and you're fired.
You are bye, bye everybody.
No no, no.
When i've had your apartment made even smaller Oh, I have to go back to the old apartment.
I'm doing zooms like down here.
I've had your ceiling lowered.
I was in junior high, high school when I thought, oh, I can actually do this.
Because when I was growing up, it was like 2010.
So there was this big comedy podcast boom.
And everybody was talking about how you could do comedy as a career.
And I feel like a lot of people before that didn't really have that sense.
And I remember there were very key moments of watching your show.
And watching the documentary the tour, doc Conan O'Brien Can't Stop where it felt like oh, this person is like – can have – you can have your problems and your anxieties.
And I was going through a lot of anxiety at the time.
But the comedy part can be like a salve.
It can get you through hard stuff.
And it like – I've never told you this really, but that documentary was like a big deal for me as like a kid being like okay, things are – crazy and scary and I'm very anxious and you can go through things and you can be OK.
And if you really commit to being funny, you can make it through stuff.
So that was part of the bug.
But it was just a bunch of, you know, YouTube had come out.
There's a podcast.
There's all this stand up.
I remember growing up watching like the blue collar comedy guys, weirdly enough.
And I was like, like the cable guy.
Jeff Foxworthy.
Jeff Foxworthy and the guy with the puppets.
Remember that guy?
Jeff Dunham.
Why do I know all that?
I don't really have him in the pocket.
The one with the really racist puppets.
And listen, when I was 13, the best thing ever.
I was like yeah, he's a jalapeno.
Why wouldn't he be a jalapeno?
That's hilarious.
He's on a stick, there's a terrorist, he's dead.
That's cool.
I didn't know.
But you know, you just kind of grow up with that and like, with the internet too, you just got so much access to it so early and then, so that's a different, that's a very different.
This is one of the things that fascinates me, talking to someone as young as you that I didn't have access to any of that.
That was not the world I was in.
There were occasionally shows that peaked out here and there that were revolutionary and amazing, but they were very few and far between.
And most of it's like, it's the love boat.
And you're like, huh?
This is our comedy.
And you're getting...
So it's not just shows you're seeing on television.
Were there sitcoms or anything that you were into?
Or is that not really... Oh, totally.
Sitcoms that were... I get 30 Rock, Community, Parks and Rec.
Those were all out in exactly the formative time that you would want to watch it.
I remember watching those shows and just being like, they're just...
Being as crazy as possible on TV.
They're making themselves happy.
Yes.
And it's very specific.
And I always really appreciated that.
So it was just something that I think in this era felt like a real viable career path.
And before I even went to college, I knew I want to do comedy.
And so I went to college for like a year.
And I was working on an English degree.
And I was like, this is a waste of time probably.
Go to college, kids.
But...
But if you're going into comedy, I don't know.
We just did a podcast with Lisa Kudrow where I ended up encouraging people to smoke.
Oh, good.
Things are going really well.
We should be shut down immediately.
You're telling kids, don't go to college.
Don't go to college.
Smoke.
Get some cigarettes, but get a lot of them.
Yeah, but the good ones.
Buy in bulk.
So you leave after a year.
Yeah.
Okay.
And then what do you do?
I moved to Chicago because, you know... From where?
Salt Lake City, Utah.
Okay.
Yeah.
Oh.
Yeah.
Yeah.
You didn't... Actually, I think I did know that.
But I associate you more with Chicago.
Yes.
I lived, I feel like I became an adult and a real person in Chicago because I grew up you know Salt Lake Mormon, the whole thing.
And so I was very sheltered and I had no sense of the world.
And...
In fact, comedy was like a lot of what gave me a sense of like, this is what other people are doing.
Whereas where we were, it was very, like, you go to church, you do all the church stuff.
You're not really supposed to watch, like, The Simpsons and stuff.
And, you know, I was, obviously.
But, like, yeah.
So comedy was also, I think, kind of what got me out of being super religious.
But I was like, I have to pursue this.
I moved to Chicago because you know you hear about Second City, you hear about stand-up, you hear about all of this improv stuff and sketch.
And I just wanted to do all of it, you know?
And so I just moved and everybody's like, that's crazy.
You're just dropping out of school to move to Chicago.
And I was like, it'll be fine.
Like I had no sense of my own mortality at 20.
So I was like, yeah, you can just like, go wherever you want and do whatever you want.
And I think I have enough of an aptitude for this that it'll be okay.
Obviously, that hasn't worked out at all, but... I keep trying to get you on a legitimate project.
Yeah.
I'm doing the best I can.
But so, how do you support yourself?
You get to Chicago.
How do you live?
Terrible jobs.
Terrible jobs.
I worked for...
One of those companies that I think the first job I had was.
One of those companies where they're like we're going to go out and help people have a better electricity.
It's just like a pyramid scheme.
I was in a pyramid scheme for a couple of days.
You do that.
You got to be in a pyramid scheme for like a little bit.
And where you go, you really do.
And they're having these meetings honestly not unlike when Conan kicks in the door to the writer's room where they coming in with all this energy and it's like what do we do?
And they're like, don't worry about that.
We're going to do it.
So, so, so it's like, what is the product?
And they're like, shut up.
You know, it's occurring to me right now that all of my career has been a pyramid scheme.
I come in with a lot of energy and it's at the end, you're just bankrupt.
Yeah, yeah, yeah, yeah.
So, okay, so you're doing a bunch of jobs like that.
Just random shitty jobs.
And then I started contributing to ClickHole, which is an offshoot of The Onion for like, the internet generation.
Yeah, I know ClickHole.
Yes, you did a video with ClickHole.
Do you remember the premise of the video you did for ClickHole?
Yes, I'm in the background, right?
Describe it, because you're going to describe it better than I can.
I remember this.
I remember when you shot it.
I don't know if I remember it, but you're pouring milk.
Yes, yeah.
I think it's a couple going through a breakup.
And the premise of the video is couple goes through breakup while Conan O'Brien pours milk into the sink in the background.
Yeah.
Pouring milk into the sink in the background.
We're in some random house.
You can kind of see me.
Yeah.
Yes.
I'm not really that featured.
Yeah.
A woman tells her husband she's pregnant.
Oh.
That's right, that's what it was.
And then you were like, this is perfectly good milk that I'm pouring down the drain.
Yeah, I was just narrating how this is good milk.
It's not that it's bad.
It's just going right down the drain.
So you were working there when I... No, I wasn't working there when you did that.
But that was probably one of those early things that probably came out when I was in high school.
And that was one of those things where it's like, if people are making that and you can do that, that is the kind of thing I want to do.
Oh, cool.
And so I remember my first headline I ever got on.
There was like heartwarming.
Even though this man and woman are from different religions, they still had sex on a park bench.
So that, you know... There you go.
Then you knew I'm on terra firma here.
This is good.
That $15, like also the first time ever getting paid for writing something.
Oh, that's huge, right?
This is amazing.
The first moment someone... And I always appreciate it and I still appreciate it.
I did a set the other night at some comedy club in Covina.
And...
After I was done, they gave me an envelope which is what happens in standup and it had a 20 bill in it.
And I took it home and I taped it to the glass that's in my closet.
You know, when I get dressed in the morning and I'm just like I taped it up.
Because I remember the first time I got anytime you get that one-to-one hit of.
I just went and had a lot of fun.
I think the audience was happy.
I had fun.
And then someone gave me a $20 bill.
Right.
It does feel like magic.
Right, because you got that 20 bill and maybe you spent like five minutes like talking about foreskin or something.
And you're like, this is money.
I did the whole set on foreskin.
All of your Oscars jokes just weird.
Weirdly, you keep being like, give me more foreskin.
We don't have enough foreskin.
We go, Conan, what about the movies?
You go, no, foreskin.
No one cares about those movies.
They want foreskin.
The whole thing.
Boy, this is gonna be a bad Oscar.
15 minutes up top about Forescape.
Yeah, just cut to stars streaming out, getting in their cars and leaving before they've even their categories been announced.
Yeah Okay, so you're doing that.
And then how did we find you?
I was fellowship writing at The Onion at the time.
Or no, no.
There was packets that go out.
The way that the Conan show, I think, always sent out packets is different than most late night shows.
Because you guys just went like, we want 10 ideas.
And you ask any follow up questions.
You're like, what do you mean ideas?
And they're just like 10 ideas.
And so I remember writing a packet.
And I put, you know, stupid little jokes in the packet.
I remember one of them, because they're just like different pitches.
And one of my pitches was just straight up like, Conan O'Brien does blackface.
And then I did a colon.
And then I just wrote, Conan O'Brien does blackface.
And it wasn't obviously a real pitch.
But I was like, well, people are going to remember that if I put that in there.
Just like, yeah, what if he did it?
And then somebody... Because, you know, you have to read like a bunch of these things.
It's a tactic to get people to be like what the hell is what's going on and then like actually read it catches the eye, it catches the eye, yeah sure.
Oh, that would be very unfunny.
Oh, that would be bad.
And you'd never hear from me again.
Yeah, but if you put it in the middle of a bunch of funny ideas like you like coming up with, like what's the worst thing I could say or do?
And I always love thinking about that stuff, too.
So I'm like, I don't know.
I thought it would just be, like, whatever.
I also did never think I would get the opportunity.
And then a year went by, and then...
It was in the middle of COVID and the onion.
And I think that there was just like you needed to hire again, but there were packets left over from last year.
And that's how it happened.
So you can tell when you look at a packet it's Mike Sweeney will say oh, you got to see this packet.
And you can tell...
Almost right away in a packet, when someone knows who they are and is kind of confident about their comedic voice.
Oh, sure.
And I think that's always what sets it apart.
Sometimes I can read a packet and I can say yeah, there's not one idea here that we could use right now.
You weren't going to use that blackface one.
We did.
Yeah, no one paid attention.
Um no uh, sometimes you don't even think oh okay, here it is idea number seven, we could use that.
And idea number nine we could use that.
That could go into the show.
So hire this person.
Sometimes you'll read a whole packet and think yeah, not one of these quite has my voice, but this is a really funny person and that is the harder thing to find, Right?
You know what I mean?
And then a funny person will come in and they'll take the temperature of what's going on here.
And very quickly we'll start just saying, oh yeah, do this, do that, do this, do that.
And maybe broaden our horizons about what could be funny.
Right.
Because we, you know, don't always know everything.
And so-
That's the idea.
It works.
That's what I find beautiful about comedy though too, is that you know, you and I are by all metrics very different people.
I think we can say that.
I don't know what you're talking about.
I think we could say that.
I think you're insane.
I would say that you can be from two very different worlds, but sort of the idiosyncrasies of, I think, comedy for comedy's sake and whatever this idea of if there is a true north in comedy, of just funny, that is kind of all the same a little bit.
Even if all the specifics are different, when something's really really funny, it can be this crazy weird sketch thing or it could be like this version of stand up or whatever it can still be really funny and you can hopefully like connect and like you gotta be able to learn how to speak different comedic languages and I feel like I had to learn how to speak the Conan language but you still end up getting like the best stuff out of this.
Person's really different, but they know how to fit their thing into our world and like look what came of it.
Like I think one of the first things I pitched at the show when we were on Zoom is that we just do a whole Christmas show because I'm like I think we're going to die.
Let's just do a Christmas show.
Yeah.
And you really liked it.
You were like, let's go.
And we did Christmas in like August, I think.
Yeah, we did.
We actually decorated the whole, I think we decorated the Largo Theater.
Yeah.
It was really fun.
It was fun.
And I was like, wow, this is... No, but also it's just, I mean...
I'm sorry you thought that.
It's so funny because I talked to so many young people people your age and younger in 2020 who really did think it was the end of the world.
Just only because I was older, I was able to say to them, No, it's okay.
This is not the end of the world.
We've been through this.
This is what happens in life.
We go through these things and we have to come together and they're scary.
And then we move on and I hope evolve.
But that is, no?
No, I'm saying we evolve.
Sure.
I mean, look at the world today.
Perfect.
Yeah, it's great.
I think we can agree there are no problems.
I agree 100%.
Kyle, we don't get out much.
So we are now, as we tape this, what are we, like a month away from the Oscars, I think.
Yeah, five weeks.
And now we're at five weeks.
And it's funny, like we get in there and, okay, you tell me.
I'm asking you.
I'm legitimately asking you.
Okay, okay.
I have always thought that the bullshitting in a writer's room isn't really just bullshitting, it's kind of essential.
And I can't prove it, but we'll go in and I think, I don't know what was happening today.
I was acting something out.
You guys are making fun of me.
It has nothing to do with the show that we have to put on in five weeks.
We're working on a lot of those.
We're being very responsible.
But we will get off on tangents where we're all laughing really hard.
And maybe it's terribly inappropriate, but some of us are practically crying.
And I will leave afterwards and I'll think, well, that was really good.
None of that will go into the show.
Yeah.
But it's serving some purpose or I'm just wrong and it's a waste of time.
No, you're right, because I've been in rooms where writers rooms where it is fun, and I've been in writers rooms where it's not fun and even on just like an essential level of just like wanting to come into work, and It is hard work sometimes.
So you are going to want to have to be there to do it.
It's important to be like, I don't know, I'm going to laugh really hard today.
And it's maybe we'll see and like or some crazy joke come up and maybe it does become something.
Probably not.
But like, it's fun to just be in the space.
Yeah.
Other times when you're trying to do comedy and you feel terrible and you're under the gun and it's like well, it's got to be exactly right.
And also people aren't supporting each other.
It's not fun to do.
It's weird.
You can be in these situations where you're like dang.
This was like my quote, unquote dream job and I feel terrible every day.
That is not, despite the fact that you are deeply abusive.
That is not-.
I gave you a good shoulder massage today.
It was a good- employer to employee shoulder massage.
I felt some knots and I went at it.
Honestly, he released my chakras.
It was really, I feel loose now.
There you go.
Did he ask you if he could first?
What do you want me to say to this?
How should I answer, boss?
I think we take the Fifth Amendment.
Okay.
I might have leapt across the room and started deeply giving Skylar a deep tissue massage.
Might have crept over like a Scooby-Doo villain in order to do that.
I did.
I came over like...
Anyway, look, I'll be jailed for my crimes.
We all know that.
But what was the biggest?
This is the question I wanted to ask before we have to wrap, which is what was the thing about working on that show last year?
The Oscars that was there something that really profoundly surprised you.
Because it's, You and I have both worked in, you know, different versions of show business.
And then there's that show.
Right.
Which is this, still this kind of big iconic thing.
Was there something that you took away from that?
I, before working on that, I had no sense of scale, I guess.
And obviously, I knew it abstractly, but I... didn't know what it would feel like being there.
And I never realized that the jokes, almost every joke, it felt like there was like a headline about like everybody's talking about this joke that you had just said like five minutes ago.
I had not experienced that before.
And it was weird to be like, oh, all eyes are on this.
And it's live and it's happening in a way that doesn't really happen that much almost ever anymore.
Like the only live comedy that you have is SNL, but it's still not the.
It's not like it's getting like millions and millions of views every week.
You know.
It's like... It was just huge.
And I had not been in a space with also, like, that many celebrities before.
Obviously you see them around, but when they're all in sort of a concentrated area, that star power is just like.
You're seeing people that you've seen your whole life just whiz by your vision.
It's like very...
I don't know, just kind of surreal.
And then it's just like alright well, let's just go back and make sure these jokes work.
Like let's go back down into that dungeon below the theater and just make sure the jokes work, because there's pretty people upstairs and it's scary.
Is that where they put you?
Downstairs in like the basement?
No, there's a room downstairs.
Because I go there too and we'll sit there and we'll think okay, we just rehearsed, but now we got to go downstairs.
Last year it was, I think Cynthia and Ariana were practicing their song and they kind of wanted to clear the area.
Oh yeah, they said, get out.
Get out for Cynthia and Ariana.
All of us.
You're not important enough.
You get out.
And all of us went down and just were all underground.
And then we were in this room and we're trying to figure out should this joke go before this joke or after that joke.
But the thing that I find is the scale can change, but the process is the same.
It is.
Meaning if we were working on a show that was just gonna be a live, fun sketch show that we were gonna perform for an audience of 200 people at the Largo Theater.
It's still the same process.
Right.
You got to have the ideas.
You got to fight over them.
You got to... And then you can change the scale.
Right.
And you can add these beautiful, iconic people, but it's still the same thing.
Yeah.
And the process isn't that much different, except I need a lot more makeup.
Right.
Oh.
It's also very gratifying.
That moment of...
I think the two days before, I don't know what it is where we're feeling kind of insane.
And you remember those last 48 hours?
It's like, we're like moving stuff around.
There was just a sense of the adrenaline that's rushing through me and being like oh, we're actually, we're really doing it.
And this has to happen and we've got to pull it off.
Some of the... best moments kind of happened.
I don't think that Jesse didn't really like.
I think it was Jesse's idea to put the sandworm in the band.
That happened like five minutes before the show.
It was like, but that's like really.
And it happened because it had to happen, because something else dropped out and we quickly said okay, if it was, I don't know who it was, but it was Jesse.
Great.
But just, oh yeah.
Um, so yeah, we're going to go do it again.
Let's hope it all goes well.
Yeah.
Things got really quiet in here.
Yeah, it did.
It's a lot of pressure for you guys.
I'll be watching.
It's no pressure for me at all.
I just enjoy it.
I was in the audience while you guys were underground.
Oh, my God.
You're always high.
We were sitting next to Kurt Russell and Goldie Hawn.
Oh, my God.
It was great for me.
I don't think you should have that good a seat.
You, like, danced with him.
It was so great.
I danced with him.
I don't think.
We took shots with Coleman Domingo.
This isn't right.
I don't know.
Coleman Domingo loves taking shots.
Oprah and Gayle were behind us.
Why are you getting such a good seat?
It's like you guys did all the work.
Why is Oprah behind you?
You had so much fun.
We were scared.
I know.
I know.
You guys are talking about the Oscars like it's scary.
And I'm just like, why?
It's fun.
But the work you do makes my life better.
I don't.
Can I go on record as saying you should not have that good a seat?
I already did.
I can't believe Oprah's like, oh, there's all this hair in front of me.
Oh, man.
All right, Skylar.
Yes, I'm going to go and throw objects at all of you in about five minutes.
But you're brilliantly funny.
I thank you for loaning your talents to me.
And onward and upward, I say.
Thanks for having me.
Onward and upward.
Conan O'Brien needs a fan.
With Conan O'Brien, Sonam Ovsessian, and Matt Gourley.
Produced by me, Matt Gourley.
Executive produced by Adam Sachs, Jeff Ross, and Nick Liao.
Incidental music by Jimmy Vivino.
Take it away, Jimmy.
Supervising Producer, Aaron Blair.
Associate Talent Producer, Jennifer Samples.
Associate Producers, Sean Doherty and Lisa Byrne.
Engineering by Eduardo Perez.
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