Staff Review With Skyler Higley

Summary

Conan O’Brien Needs A Friend

Episode: Staff Review With Skyler Higley
Date: March 12, 2026

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Episode Overview

This lively episode takes a behind-the-scenes look at Conan O'Brien’s writer’s room as he sits down with staff writer Skyler Higley to discuss Skyler's comedic journey, his unconventional rise in the industry, and his contributions to Conan’s late-night and Oscar work. Amidst playful roastings, the two reflect on the craft, generational shifts in comedy, writers’ room culture, and the sometimes surreal experience of writing for the Oscars. Throughout, the tone is warm, irreverent, and packed with rapid-fire jokes and affectionate ribbing.

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Key Discussion Points & Insights

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Skyler’s Origin Story & Early Comedy Influences

[01:37] – [04:59]

• Conan invites Skyler to share his background, noting that while the staff spends much time together, he often doesn’t get to know writers deeply.
• Skyler jokes about Conan’s unusually respectful tone at first, expecting the usual over-the-top, theatrical ribbing Conan gives in the writers’ room.
  • "[Conan:] I kick the door open like it's a drug raid...and then I start doing cartoonish, over-the-top insults." [02:33]
  • "[Skyler:] That's what I was waiting for." [02:55]
• Skyler recaps his hiring during the pandemic (2020, amid BLM protests in Chicago)—an anxious, surreal time:
  • "Remember when we cared about BLM for a second?...then people called me up and were like, hey, do you want to meet with Conan's people?...Well, I think the world's ending, so sure." [03:50]

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Zoom Beginnings and Life Underground

[04:59] – [05:25]

• Conan describes the hilariously cramped appearance of Skyler's Chicago apartment during pandemic-era Zooms, comparing it to Being John Malkovich and joking Skyler looked "held captive."
  • "[Conan:] You would appear on the screen and it looked like your ceiling was one inch above your head." [05:14]
  • "[Skyler:] It wasn't the angle. I lived underground...cheap rent when you live underground." [05:24]

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The Craft: Comedy as Connection & Salve

[07:41] – [09:24]

• Skyler talks about discovering the possibility of a comedy career through the early 2010s podcast boom and platforms like YouTube.
• He credits watching Conan O’Brien Can’t Stop and Conan’s shows with normalizing anxiety and showing the therapeutic aspect of comedy:
  • "The doc...was a big deal for me as, like, a kid...if you really commit to being funny, you can make it through stuff." [08:11]
• Early influences included both stand-up (Blue Collar Comedy, Jeff Dunham) and new-era sitcoms like 30 Rock, Community, and Parks and Rec.
  • "They’re being as crazy as possible on TV and they're not happy. They're making themselves happy." [10:55]

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Skyler’s Leap: From Salt Lake to Chicago

[11:44] – [14:16]

• Skyler leaves college early, moving from conservative Salt Lake City to Chicago to pursue comedy and soak up the Second City and improv scene.

  • "Comedy...kind of what got me out of being super religious...You hear about Second City...just wanted to do all of it." [12:29]

• Survival jobs: Skyler did “terrible jobs,” including a humorous stint in a pyramid scheme:

  • "[Skyler:] I was in a pyramid scheme for a couple days." [13:42]
  • Conan draws parallels between pyramid-scheme energy and his own writers’ room antics.

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Breaking In: Clickhole, The Onion & Conan’s Hiring Process

[14:16] – [15:52], [21:59] – [23:35]

• Skyler starts pitching for Clickhole, earning a first $15 writing check (a pivotal moment).
  • "First time ever getting paid for writing something, like, huge." [15:47]
• When applying for Conan, Skyler notes the show’s unique “packet” process: just submit 10 ideas, no details.
  • "[Skyler:] One of my pitches was just straight up like, 'Conan O'Brien does blackface.' ...It wasn’t obviously a real pitch, but I was like, well, people are gonna remember that." [22:36]
  • Conan and Skyler both emphasize that what sets great packets apart is a clear, confident comedic voice, not just reusable material.
  • "[Conan:] 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." [23:35]

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Writers’ Room Culture & Why Bullshitting Matters

[27:38] – [29:58]

• Conan defends the value of chaos and goofing off in the writers’ room:
  • "I have always thought that the bullshitting in a writer’s room isn’t really just bullshitting. It’s kind of essential." [27:38]
• Skyler fully agrees, describing positive and negative writers’ room environments:
  • "[Skyler:] Other times when you’re trying to do comedy and you feel terrible and you’re under the gun and it's gotta be exactly right...it’s not fun to do." [29:33]
• Affectionate roasts continue: Conan jokes about giving Skyler a (possibly inappropriate) shoulder massage, leading to more banter about workplace boundaries.

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Writing for the Oscars: Pressure & Surreal Moments

[30:08] – [34:03]

• Skyler and Conan reflect on the scale and immediacy of writing for the Oscars, from underground "dungeon" writers’ rooms to watching their jokes create headlines minutes after broadcast:

  • "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." [30:44]
  • "All eyes are on this. And it's live...I had not been in a space with...that many celebrities before." [31:52]

• Conan adds: the process is the same whether for 200 at Largo or millions at home—it’s about fighting for the best ideas:

  • "[Conan:] The scale can change, but the process is the same." [32:43]

• Last-minute creative chaos: The now-famous addition of "the Sandworm in the band" was a five-minutes-before-show inspiration—demonstrating the adrenaline and improvisation at this level.

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Notable Quotes & Memorable Moments (with Timestamps)

• Conan on Writers’ Room Entrances:
  "I kick the door open like it’s a drug raid… and I start doing cartoonish, over-the-top insults." [02:33]

• Skyler on Getting the Job:
  "I was like, well, I think the world's ending, so sure." [03:50]

• Conan on Early Zooms:
  "Your ceiling was one inch above your head, and it looked like you were being held captive." [05:14]

• Skyler on Comedy as Therapy:
  "That documentary was...a big deal for me...I was very anxious, and you can go through things and you can be okay, and if you really commit to being funny, you can make it through stuff." [08:11]

• Skyler’s Packet Tactic:
  "One of my pitches was just straight up like, 'Conan O'Brien does blackface.' ...It wasn’t obviously a real pitch, but...what if you did it and then somebody...it’s a tactic to get people to be like, what the hell is what's going on? And then actually read it." [22:36]

• Conan on Recognizing Comedic Voice:
  "You can tell almost right away in a packet when someone knows who they are and is kind of confident about their comedic voice." [23:35]

• On Writers’ Room Bonding:
  "I have always thought that the bullshitting in a writer’s room isn’t really just bullshitting. It’s kind of essential." [27:38]
  "Other times when you’re trying to do comedy and you feel terrible and you’re under the gun...it’s not fun to do. It's weird. You can be in these situations where you’re like, this was my ‘dream job’ and I feel terrible every day." [29:33]

• On Oscar Night:
  "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." [30:44]

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Structure & Flow

The episode is structured as a loose, organic conversation, with Conan guiding the discussion but allowing Skyler’s humor and stories to set the tone. Listeners are treated to:

• Warm, irreverent banter about inside writers’ room dynamics.
• Skyler’s candid recollections of breaking into comedy in new media’s golden age.
• Practical, real-talk about the pressures and rewards of late-night and awards show writing.
• Layered with rapid-fire jokes and affectionate “insult comedy” typical of Team Coco.
• Occasional drops of sincerity about finding one’s comedic voice and using humor to process anxiety and chaos.

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Timestamps of Key Segments

• [01:37] – Beginning; introduction to staff interviews and the writers’ room atmosphere
• [03:50] – Skyler recounts his hiring during the height of COVID/blm protests
• [05:01] – Skyler’s underground apartment Zoom setups
• [08:11] – Comedy as solace, Skyler’s early influences
• [14:16] – First paid comedy writing at Clickhole
• [21:59] – Applying to Conan, writing packets, finding a comedic voice
• [27:38] – Writers’ room “bullshitting” as an essential creative process
• [30:08] – First-hand account of writing for the Oscars, live pressure
• [32:43] – The universal writing experience – process vs. scale
• [33:47] – Last-minute Oscar changes / adrenaline moments
• [34:43] – David Hopping’s luxury Oscar seat and wrap-up banter

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Final Thoughts

This episode showcases the unique chemistry of the Team Coco writing staff. Skyler Higley’s personal story illustrates the democratization of comedy careers for a new generation, while the interplay with Conan highlights how much great comedy relies on collective chaos, difference, and collegial disrespect. If you’re interested in the mechanics, anxieties, and joys of comedy writing, or the transition from late night to live, high-stakes Hollywood events, this conversation pulls back the curtain with both heart and humor.

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Transcript

[Conan O'Brien]

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[Skyler Higley]

Fools.

[Conan O'Brien]

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[David Hopping]

Conan o' Brien needs a fan. Want to talk to Conan? Visit teamcoco.com call Conan. Okay, let's get started.

[Conan O'Brien]

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. 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. Cause they're very funny, very talented, and today it is Skyler Higley's turn. Skyler, let's hear your origin story. Where are you from?

[Skyler Higley]

Can I first say, this is the most respectful I've ever heard you speak to me.

[Conan O'Brien]

Thank you.

[David Hopping]

That's what I said last time.

[Skyler Higley]

The Conan O'. Brien. Yeah. I love these writers.

[David Hopping]

Yes.

[Skyler Higley]

In 20 minutes, gonna be different.

[Conan O'Brien]

Let me tell you 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.

[Skyler Higley]

That's what I was waiting for just now, actually.

[Conan O'Brien]

But then I realize I don't have my glasses.

[David Hopping]

Oh, okay.

[Conan O'Brien]

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 all theater, but I think, I know. I have a good time.

[Unidentified Writer/Producer]

We have a great time. And then we wait for you to

[Skyler Higley]

leave, and then we work.

[Conan O'Brien]

Yeah. Then you get back to some, right? 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.

[David Hopping]

And you ruined the door downstairs.

[Conan O'Brien]

I kind of did.

[Skyler Higley]

There are scuff marks on it every day.

[Conan O'Brien]

Yeah, I know. I know.

[Skyler Higley]

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.

[Conan O'Brien]

I don't. I don't tire myself out. Skyler. Yes, Tell me. I remember when you first started working for me, which would be. What year did you start working for me?

[Skyler Higley]

2020.

[Conan O'Brien]

Okay.

[Skyler Higley]

Remember in the middle of the pandemic and there was the blm. Remember when we cared about BLM for a second? 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. 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.

[Unidentified Writer/Producer]

Like, there was a virus. There was like an uprising of social.

[Skyler Higley]

You know, it was like, fine, yeah,

[Conan O'Brien]

this'll be the last thing I do. But what I remember most is that because everything. You still. You didn't move. Cause it's the height of, you know, not just Covid, but much insanity. So you would zoom in from your apartment, and your apartment was in Chicago. And I remember the angle was. I don't know if it was how much of it was the angle and how much of it was the angle.

[Skyler Higley]

It wasn't the angle. I lived underground.

[Conan O'Brien]

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.

[Skyler Higley]

Yeah.

[Conan O'Brien]

And it looked like you were being held captive.

[Unidentified Writer/Producer]

It looked like in being John Malkovich,

[Skyler Higley]

when he has to go into John

[Unidentified Writer/Producer]

Malkovich's head and the ceiling's really low.

[Skyler Higley]

That's kind of where I live.

[Conan O'Brien]

Yeah, yeah, yeah.

[Skyler Higley]

But it cheap rent when you live underground. Let me tell you something.

[Conan O'Brien]

Well, 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.

[Skyler Higley]

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.

[Conan O'Brien]

Oh, I think there was a sense before I went out, I thought, well, this'll be fun.

[Skyler Higley]

Yeah.

[David Hopping]

Yeah.

[Conan O'Brien]

And I don't wanna misquote it, so maybe you can remind us. I walk back out, it's the beginning of an act.

[Skyler Higley]

Beginning of the midway point, which is important. Cause 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.

[Conan O'Brien]

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 cures me of any ailment I might have had. Huge. And then I walk right backstage and there you are, all nicely dressed. I think I gave you a. Yeah, thank you. Yeah.

[Unidentified Writer/Producer]

And then you were like, your name is Skyler, right?

[Conan O'Brien]

It's.

[Unidentified Writer/Producer]

I noticed the moment Conan started respecting

[Skyler Higley]

me as a person.

[Conan O'Brien]

Yeah. Yeah. Well, started to.

[Unidentified Writer/Producer]

Started.

[Conan O'Brien]

And then you spent that capital really quick.

[Skyler Higley]

Oh, of course.

[Conan O'Brien]

But I'm curious. I haven't really sat down and talked to you about your backstory. When do you start thinking, okay, 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 Skyler Higley?

[Skyler Higley]

I got the bug, you know, early. Like, as kids, I feel like I was like, I feel isolated. I feel like a weirdo. You know, a thing or two about that and you're fired.

[Conan O'Brien]

You are.

[Skyler Higley]

Bye. Bye, everybody. No, no, no.

[Conan O'Brien]

Oh, and I've had your apartment made even smaller.

[Unidentified Writer/Producer]

Oh, I have to go back to the old apartment.

[Conan O'Brien]

Yes, you have to.

[Unidentified Writer/Producer]

No, I'm doing zooms.

[Conan O'Brien]

Like, has your ceiling lowered.

[Unidentified Writer/Producer]

I was in.

[Skyler Higley]

Yeah, like, 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, you know, 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 the doc. 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 okay, 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 podcasts, there's all this standup. I remember growing up watching, like, the blue collar comedy guys, weirdly enough, and

[Conan O'Brien]

I was like, larry the cable guy. Yeah, Jeff Foxworthy.

[Unidentified Writer/Producer]

Jeff Foxworthy.

[Skyler Higley]

And the guy with the puppets.

[Unidentified Writer/Producer]

Remember that guy?

[Commercial Voice 1]

Jeff Dunham.

[Conan O'Brien]

Why do I know?

[Unidentified Writer/Producer]

You were ready.

[Skyler Higley]

The one with the really racist puppets.

[Unidentified Writer/Producer]

And listen, when I was 13, the

[Skyler Higley]

best thing ever, I was like, yeah, he's a jalapeno.

[Unidentified Writer/Producer]

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. Oh, my God. I didn't know. But, you know, you just kind of

[Skyler Higley]

grow up with that and, like, with the Internet, too. You just got so much access to it so early and then.

[Conan O'Brien]

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. Yeah, 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, right. 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.

[Skyler Higley]

Oh, totally. Sitcoms that were 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 and they're not happy.

[Conan O'Brien]

They're making themselves happy.

[Skyler Higley]

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 you don't have. If you're going into comedy.

[Conan O'Brien]

We just did a podcast with Lisa Kudrow. We were. I ended up. I ended up encouraging people to smoke.

[Commercial Voice 2]

Oh, good.

[Unidentified Writer/Producer]

Things are going really well.

[Conan O'Brien]

We should be shut down immediately. You're telling kids, don't go to college.

[Unidentified Writer/Producer]

Don't go to college.

[Conan O'Brien]

Get some cigarettes. But get a lot of them.

[Unidentified Writer/Producer]

Yeah.

[Skyler Higley]

With the good ones.

[Unidentified Writer/Producer]

Buy in bulk.

[Conan O'Brien]

So you leave after a year.

[Skyler Higley]

Yeah.

[Conan O'Brien]

Okay. And then what do you do?

[Skyler Higley]

I moved to Chicago because, you know.

[Conan O'Brien]

From where?

[Skyler Higley]

Salt Lake City, Utah.

[Conan O'Brien]

Okay.

[Skyler Higley]

Yeah. Oh, yeah, yeah. You didn't.

[David Hopping]

Yeah, actually, I think I did know that. But I associate you more with Chicago.

[Skyler Higley]

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 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 the Simpsons and stuff. And, you know, I was obviously. But, like.

[Conan O'Brien]

Yeah.

[Skyler Higley]

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. 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,

[Conan O'Brien]

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?

[Skyler Higley]

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 days.

[Unidentified Writer/Producer]

You do that. You got to be in a pyramid

[Skyler Higley]

scheme for, like, a little bit.

[Unidentified Writer/Producer]

And where you go.

[Conan O'Brien]

You really do.

[Unidentified Writer/Producer]

And they're having these meetings, honestly, not

[Skyler Higley]

unlike when Conan kicks in the door to the writers room, where they coming

[Unidentified Writer/Producer]

in with all this energy. And, yeah, we're going to do it. And it's like, what do we do? And they're like, don't worry about that. We're going to do it. Sell, sell, sell. It's like, what is the product? And they're like, shut up.

[Conan O'Brien]

You know, it's occurring to me right now that all of my career has been a pyra. I come in with a lot of energy, and at the end, you're just bankrupt. Yeah, yeah, yeah, yeah. So, okay, so you're doing a bunch

[Skyler Higley]

of just random shitty jobs. And then I started contributing to Clickhole, which is an offshoot of the Onion for, like, the Internet generation.

[Conan O'Brien]

I know. Clickhole.

[Skyler Higley]

Yes. You did a video with Clickhole.

[Conan O'Brien]

Where?

[Unidentified Writer/Producer]

Do you remember the premise of the

[Skyler Higley]

video you did for Clickhole?

[Conan O'Brien]

Yes. I'm in the background. Right. So describe it. I can't, because you're gonna describe it.

[David Hopping]

I remember this. I remember when you shot it.

[Conan O'Brien]

I don't know.

[Skyler Higley]

I don't know if I'm in the background pouring milk.

[Conan O'Brien]

Yes. Yeah.

[Skyler Higley]

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.

[Conan O'Brien]

Yeah, I'm pouring milk in the sink in the background. You can kind of see me.

[Unidentified Writer/Producer]

Yeah.

[David Hopping]

Yes.

[Conan O'Brien]

It's not. I'm not really. That featured woman tells her husband she's pregnant.

[Unidentified Writer/Producer]

Oh, my God.

[Commercial Voice 1]

That's right.

[Conan O'Brien]

That's what it was.

[David Hopping]

And then you were like, this is pretty perfectly good milk that I'm.

[Conan O'Brien]

That was my line 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. Yeah. So you were working there when I.

[Skyler Higley]

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.

[Conan O'Brien]

Oh, cool.

[Skyler Higley]

That's great. And so I. I remember my first headline I ever got on there was like. 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.

[Conan O'Brien]

Then you knew I'm on terra firma here.

[Skyler Higley]

That $15, like, also the first time ever getting paid for writing something, like, huge.

[Conan O'Brien]

Right?

[Skyler Higley]

This is amazing.

[Conan O'Brien]

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 Stand Up. 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 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. 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.

[Skyler Higley]

Right? Because you got that $20 bill, and maybe you spent like five minutes, like, talking about foreskin or something, and you're

[Unidentified Writer/Producer]

like, this is money.

[Conan O'Brien]

I did a whole. I did the whole show on foreskin.

[Unidentified Writer/Producer]

All of your Oscars jokes.

[Skyler Higley]

This weird.

[Unidentified Writer/Producer]

Weirdly, you keep being like, give me more.

[Conan O'Brien]

We don't have enough foreskin.

[Unidentified Writer/Producer]

We go, conan, we. What about the movies? You go, no foreskin.

[Conan O'Brien]

No one cares about those movies. They want foreskin.

[Skyler Higley]

So the whole thing, boy, this is

[Conan O'Brien]

going to be a bad Oscar. 15 minutes up top About Forskin.

[Unidentified Writer/Producer]

Yeah.

[Conan O'Brien]

Just cut to stars streaming out, getting in their cars and leaving before they've they've even their category's been announced.

[Skyler Higley]

Yeah.

[Conan O'Brien]

Say hello to the all new Alexa plus and see how Alexa can do so much more for you. Need last minute concert tickets? Craving your favorite restaurant? Just sit back, relax and talk naturally. Alexa's on it. You know what? I cannot speak naturally. I've never done that.

[David Hopping]

It's okay.

[Conan O'Brien]

Alexa's always telling me to calm down.

[David Hopping]

I feel like you'll yell at it.

[Conan O'Brien]

No, I would never yell at Alexa. Alexa remembers what you love, anticipates what you need, and makes it all happen. Alexa plus brings thousands of possibilities to life, ready whenever inspiration strikes. And now Alexa is free with prime on your Amazon devices like echo and Fire TV. Amazon.com Alexaplus you know, there are days that the travel perks that you get with T Mobile really come in handy. But then there are days that you just want to embrace couch life. And you love you some couch life.

[David Hopping]

I loves me some couch life.

[Conan O'Brien]

And without ever leaving the house, T Mobile still has you covered. Find plans including Netflix plus deals on DoorDash. The more benefits you use, the more value you get. I mean, why go anywhere when you can get your favorite takeout, binge a show and brag to all your friends? You won't believe what I'm not doing tonight. That's a brag. When you get to hang out on your couch and live life at its most supreme.

[David Hopping]

It's so comfortable.

[Conan O'Brien]

I have T Mobile. It's great.

[Skyler Higley]

And I always like to watch those survival shows. And I like to get meat.

[Conan O'Brien]

So like a steak and then like a survival show. Yeah. And then the monster's eating the person. You like the meat. Pretend of the mon you're a sick guy. Check it out@t mobile.com magentastatus wow. Receive Netflix standard with ads while you maintain a qualifying line in good standing. See DashPass details in the tealife app. You know, I value hard work. I just do. I have an incredible work ethic.

[David Hopping]

Yep.

[Conan O'Brien]

And that brings me to Nutrigrain. Nutrigrain is a hard working snack. Okay.

[David Hopping]

I was wondering where you were going.

[Conan O'Brien]

Well, of course, the minute David knew. The minute I said hard work, he knew nutrition. Nutrigrain is coming. It's a hard working snack that fits into real life and it helps hard working people get it done. Let me explain.

[Skyler Higley]

Yeah.

[Conan O'Brien]

It's made with 10 grams of whole grains, 10 vitamins and minerals and no high fructose corn. Syrup? Yeah, Nutrigrain's portable and I demand that of a snack. Yeah, I demand that it be portable. Sometimes a great snack will come out and it's over £600. I can't lug that around.

[Skyler Higley]

£600.

[Conan O'Brien]

It's great for a grab and go option. Busy. I'm going to grab my Nutrigrain bar. Chomp, chomp. And I'm doing my best work ever. Yeah, you can choose between strawberry flavored Nutrigrain for a delicious classic or new Nutrigrain Crunchy for something new. You didn't see that coming, did you? Do you guys think you're hard working enough to merit these new nutrigrain bars?

[David Hopping]

Obviously, I don't know. I don't know if there's more hard working assistants.

[Conan O'Brien]

Okay, tell me what you do and I will assess if you're hard working enough.

[Commercial Voice 1]

You know what?

[David Hopping]

You look really nice today. I massaged your ego, which is important because you go up in front of an audience.

[Conan O'Brien]

So you don't mean it?

[Unidentified Writer/Producer]

No, it's horrible.

[Conan O'Brien]

It looks terrible.

[Skyler Higley]

Yeah.

[Conan O'Brien]

Okay, well, you know what? That does take a lot of energy to lie to a man with an incredibly fragile ego.

[David Hopping]

Yes.

[Conan O'Brien]

And you've been doing that for years.

[David Hopping]

For years.

[Conan O'Brien]

That's a ton of work. I think you might merit a nutrigrain bar. But let's see about David Hopping David.

[Skyler Higley]

What do you mean? I want to state the obvious.

[Unidentified Writer/Producer]

You're here right now, which means that this.

[Skyler Higley]

This recording was in your calendar.

[David Hopping]

There you go.

[Conan O'Brien]

You do my calendar. So you think you are hardworking because you clicked into a computer and typed

[Skyler Higley]

you know what and then hit save.

[Conan O'Brien]

I'm proud of both of you.

[David Hopping]

You're welcome.

[Conan O'Brien]

You're both hard workers.

[Skyler Higley]

Yeah.

[Conan O'Brien]

Find nutritious and always delicious nutrigrain bars at your favorite store or online retailer today. And look for new Nutrigrain crunchy bars in stores near you. Steve Carell stars in the new HBO original comedy series Rooster. From a creator of Ted Lasso and Shrinking comes the story of an acclaimed author who finds himself teaching on a college campus alongside his adult daughter, navigating their complicated relationship and Greg's late in life first chance at the college experience he never had. Is there anyone funnier than Steve Carell? I do not think there is. So I will watch this. Be sure to check out Rooster now streaming exclusively on HBO Max, subscription required. Visit HBOMax.com for details. Okay, so you're doing that and then how did we find you?

[Skyler Higley]

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 stupid little jokes in the packet. I remember one of them because they're just different pitches. And one of my pitches was just straight up like, conan o' Brien does blackface.

[Unidentified Writer/Producer]

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 gonna remember that if I put that in there. Just like, yeah, what if you did it and then somebody. Cause you know, you have to read

[Skyler Higley]

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 actually read it.

[Conan O'Brien]

It catches the eye.

[Unidentified Writer/Producer]

It catches the eye.

[Conan O'Brien]

Yeah, sure. Oh, that would be very unfunny and you'd never hear from me again.

[Skyler Higley]

Yeah.

[Unidentified Writer/Producer]

But if you put it in the

[Skyler Higley]

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 Yep, yep, that's how it happened.

[Conan O'Brien]

So you can tell when you look at a packet, Mike Sweeney will say, oh, you gotta 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.

[Skyler Higley]

Oh, sure.

[Conan O'Brien]

I think that's always what sets it apart. It isn't. Sometimes I can read a packet and I could say, yeah, there's not one idea here that we could use right now. But this is.

[Skyler Higley]

You weren't gonna use that blackface one.

[Conan O'Brien]

We did. Yeah. No one paid attention? No. 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. 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 will start just saying, oh, yeah, do this, do that, do this, do that, and maybe broaden our horizons about what could be funny. Because we don't always know everything. And so. So that's the idea. It's that those. It works.

[Skyler Higley]

That's what I find beautiful about comedy, though, too, is that you and I are, by all metrics, very different people.

[Unidentified Writer/Producer]

I think we can say that.

[Conan O'Brien]

I don't know what you're talking about.

[Skyler Higley]

I think we could say that.

[Conan O'Brien]

I think you're insane.

[Unidentified Writer/Producer]

I would say that you can be

[Skyler Higley]

from two very different worlds. But sort of the idiosyncrasies of, I think, comedy for comedy's sake and whatever. This idea of, like, a. If there is a true, like, north in comedy, of just, like, funny, that is, like, kind of all the same, a little bit. Even if all the specifics are different, when something's, like, 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. Cause I'm like, I think we're gonna die. Let's just do a Christmas show.

[Unidentified Writer/Producer]

And you really liked it. You were like, let's go.

[Skyler Higley]

And we're like, we did Christmas in,

[Unidentified Writer/Producer]

like, August, I think.

[Conan O'Brien]

Yes. Yeah, we did. We actually decorated the whole. I think we decorated the Largo theater. Yeah, it was really fun.

[Skyler Higley]

It was fun. And I was like, wow, this is.

[Conan O'Brien]

No, but also, it's just. I mean, I'm sorry you thought that. It's so funny. Cause 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. And 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.

[David Hopping]

No, no, I'm saying, did we evolve?

[Skyler Higley]

Sure.

[Conan O'Brien]

I mean, look at the world today. Perfect. Yeah.

[Skyler Higley]

It's great.

[Unidentified Writer/Producer]

I think we can agree there are no problems.

[Conan O'Brien]

I agree 100%. 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.

[Skyler Higley]

Yeah, five weeks.

[Conan O'Brien]

And now we're getting five weeks. And it's funny. We get in there and. Okay, you tell me. I'm asking you. I'm legitimately asking you.

[Skyler Higley]

Okay, Okay.

[Conan O'Brien]

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.

[Skyler Higley]

No, you're right.

[Unidentified Writer/Producer]

Because I've been in rooms where writers

[Skyler Higley]

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 gonna want to have to be there to do it. It's important to be like, I don't know. I'm gonna laugh really hard today. And it's. Maybe we'll see. Or some crazy joke come up and maybe it does become something. Probably not. But like. Like, it's fun to just be in the space. 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 gotta 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.

[Conan O'Brien]

I gave you a good shoulder massage today.

[Skyler Higley]

Employer to employee shoulder massage.

[Conan O'Brien]

I got in there, I felt some knots, and I went at it.

[Skyler Higley]

Honestly.

[Unidentified Writer/Producer]

He released my chakras.

[Skyler Higley]

It was really. I feel loose now.

[Conan O'Brien]

There you go.

[David Hopping]

Did he ask you if he could first?

[Skyler Higley]

What do you want me to say to them?

[Unidentified Writer/Producer]

How should I answer?

[Conan O'Brien]

I think we take the Fifth Amendment.

[Skyler Higley]

Okay.

[Conan O'Brien]

I might have left across the. And started deeply giving Skyler a deep tissue massage. Yeah.

[Skyler Higley]

Might have crept over like a Scooby Doo villain in order to do it.

[Conan O'Brien]

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, which is this still this kind of big, iconic thing. Was there something that you took away from that? I.

[Skyler Higley]

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.

[Conan O'Brien]

Yeah, it is so funny.

[Unidentified Writer/Producer]

And then it's just like, all right,

[Skyler Higley]

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.

[David Hopping]

Is that where they put you upstairs

[Conan O'Brien]

in, like, the basement room downstairs? Because I go there, too. And we'll sit there and we'll think, okay, we just rehearsed, but now we gotta 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.

[Unidentified Writer/Producer]

They said, get out, get out, get out. For Cynthia and Ariana, all of us, you're not important enough. You get out.

[Conan O'Brien]

And all of us went down and just swirl underground, like. 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. And. But the thing that I find is the scale can change, but the process is the same.

[Skyler Higley]

It is.

[Conan O'Brien]

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.

[Skyler Higley]

Right.

[Conan O'Brien]

You gotta have the ideas. You gotta fight over them. You gotta. And then you can change the scale and you can add these beautiful, iconic people. But it's still the same thing.

[Skyler Higley]

Yeah.

[Conan O'Brien]

And the process isn't that much different. Except I need a lot more makeup.

[Skyler Higley]

Right.

[Conan O'Brien]

Oh.

[Skyler Higley]

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.

[Unidentified Writer/Producer]

But that's like, really?

[Conan O'Brien]

And it happened. Cause it had to happen. Cause something else dropped out. And we quickly said, okay. I think it was. I don't know who it was, but Jesse. Great. But just. Oh, yeah. So, yeah, we're gonna go do it again. Let's hope it all goes well.

[Skyler Higley]

Yeah.

[Conan O'Brien]

Things got really quiet in here. Yeah.

[David Hopping]

It's a lot of pressure for you, Skyler. I'll be watching. It's no pressure for me at all. I just enjoy. I was in the audience.

[Skyler Higley]

Yeah.

[David Hopping]

While you guys were underground.

[Conan O'Brien]

You're always high.

[David Hopping]

We were sitting next To Kurt Russell.

[Conan O'Brien]

Whoa.

[David Hopping]

And Goldie Hawn. Oh, my God. It was great.

[Conan O'Brien]

I don't think you should have that good a seat.

[David Hopping]

You, like, dance so great. I danced with him.

[Conan O'Brien]

I don't think we took shots with Coleman Domingo. I don't know.

[Unidentified Writer/Producer]

Coleman Domingo loves.

[David Hopping]

Him and Gail were behind.

[Conan O'Brien]

Why are you getting such a good

[David Hopping]

seat, Oprah behind you.

[Unidentified Writer/Producer]

So much fun. We were scared. I know.

[Conan O'Brien]

I know.

[David Hopping]

You guys are talking about the Oscars like it's scary, and I'm just like, why? It's fun.

[Conan O'Brien]

Yeah. Okay.

[David Hopping]

The work you do makes my life better.

[Conan O'Brien]

I don't. Can I go on record as saying you should not have that good a seat?

[David Hopping]

I already did.

[Conan O'Brien]

I can't believe Oprah's like, oh, there's all this hair in front of me. All right, all right, Skyler. Yes. I'm gonna 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.

[Skyler Higley]

Thanks for having me.

[Conan O'Brien]

And upward.

[Narrator/Producer]

Conan o' Brien needs a fan With Conan o' Brien, Sonam of Session and Matt Gourley Produced by me, Matt Gourley executive produced by Adam Sachs, Jeff Ross and Nick Leow Incidental music by Jimmy Vivino Take it away, Jimmy. Supervising producer Aaron Blair associate talent producer Jennifer Samples Associate producers Sean Doherty and Lisa Berm Engineering by eduardo Perez get three free months of SiriusXM when you sign up at SiriusXM.com Kona Please rate, review, and subscribe to Conan O' Brien needs a fan. Wherever fine podcasts are downloaded,

[Commercial Voice 1]

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[Commercial Voice 2]

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