Molly McNearney

Welcome, welcome, welcome to Armchair Expert, Experts. on Expert. I'm Randall Shepard, I'm joined by Lily Padman. Hi there. And we have one of our absolute buddiest, our dearest buddies on today.

So fun.

Molly McNearney. She, of course, is the co-head, writer and executive producer of Jimmy Kimmel Live. Yes. She's also married to Jimmy Kimmel, Inside Scoop, and a part of many of my vacations.

Yeah, she is a real force to be reckoned with.

A powerhouse writer. She also writes on the Primetime Emmys, the Oscars, Murder Mystery. She's prolific and insanely talented, and I adore her so much. This is really fun.

So fun. So glad she came by.

All right, please enjoy Molly McNearney.

♪ He's an armchair expert ♪.

♪ He's an armchair expert ♪.

♪ He's an armchair expert ♪.

I do hot water.

Oh, I love that. It's like Howard Stern drinks, you know, hot water. Oh, really? Yes. All he drinks, cut out coffee, tea, everything, just hot water.

It's a little sad. It's a little sad.

But I also like being in his company. Yeah, it's good company. Hi!

We had a creative difference this morning, so I just wanted to let you know.

Oh, not really.

It's like only our fourth in six years, so.

Oh, that's not bad.

It was a tiny one. It happens.

Jimmy, and I have those all the time.

Well, yeah, I imagine. And similarly, we're best friends and we're coworkers, so normally you can get into it at work, but like, well, whatever. Weekend's here. It'll blow over by Monday. But no, we're going to the same place on Saturday.

Yeah, it's gotta be figured out.

And maybe it's good, cause it's like, it has to be addressed, so in that way, maybe it's good. But also, it's tricky. In some ways it's good, but in some ways it's bad.

I'm gonna get over to the mic, cause, yeah, yeah. Yeah, yeah, yeah. This is what the fucking creative difference was about. Right, right, right, right.

How do you know? I'm good. I'm excited.

Excited in the middle of it.

Did you get everything you want to drink? Yeah. You want a coffee? Water, actually.

You got one right there.

Oh, thank you.

Perfect. Let us know if you want us to heat it up. Oh yeah, I was just telling her that Howard Stern just drinks hot water. It's all he drinks. Oh, really?

You know, we just were interviewing somebody, and they had worked with Howard. I think they took his on-air persona a little seriously. Mind you, certainly she worked with him longer than I've hung out with him. But I was like, you know, I think he's very mindful of not alienating his audience, and that they know he's got $500 million. So the only way he can right-size, that is he has to be miserable everywhere he goes.

I think there's truth to that. I also think he is kind of miserable.

Interesting.

Well, yeah. We were just at his house for his 70th birthday, and the first thing he says, I can't believe I'm 70, and he's so upset that he's 70.. He's apologizing to his wife for being 70.. And I don't think he enjoys it. I was telling Monica, I just wanted to, like, you're Howard Stern, look at your life.

Yes.

Yes, but then you must ask yourself the question, with contentment and happiness, is he, Howard Stern? Like, what part of it, is the fuel for the thing?

Totally, because then what's the content?

Yes. And then I guess you're making a decision in your life, what am I gonna prioritize? And hopefully you'd be healthy and you'd be like, at least at this point, maybe I'm gonna prioritize my life. Absolutely. And say goodbye to the content or whatever.

But God, I love his content so much. I hate it when you're miserable.

I will say it's a fluke. I think it's bad thinking, because we have some friends who are very negative, and it is not helping them. So this idea that it's relatable to be negative, I just want to put a big X through that.

We have our-.

I got mad the other day about it. You did. Every time you text, if, 99% of the time you're gonna hear something negative, I can handle that up to a certain extent, but I do snap after a while.

Sure.

And then, good, I think. I think it's healthy to snap at that.

Minimally, it makes you not want to reach out.

Yeah, of course. Right.

What do you think is one of the negative things you use to motivate yourself? Because I have a bevy of them.

I never think I'm doing enough. I'm never doing enough for my career. I'm never doing enough for my children. I'm never doing enough for me, and I constantly am telling myself that.

The most bonded I've felt to Lincoln yet was we were laying in bed the other day, and we were talking about embarrassing moments, and she loves hearing my embarrassing moments. She's like, give me another one. What's another thing? And then, so I was like, well, what's some of yours? And she's like, oh, I farted at school, and blah, blah, blah, and then this and that, and I was great.

To yourself.

To ourselves.

That's so sad, but also so great that you can ask her that, and she can tell you that. I know.

Yeah, it felt just really bonding, like we're similar.

Yeah, I beat myself up pretty good, but then I'm really good at helping other people not beat themselves up. I'm always telling my friends, you're a terrible friend to yourself. Why would you speak about yourself that way? I can see it with everyone else when it comes to me.

Giving advice you need yourself.

Exactly, I'm really good at that.

I'm so excited that you're here. Are you nervous?

I am nervous. I'm not nervous. No, seem it. No, I'm really excited to be here. As you know, I'm such a fan of this podcast and such a fan of both of you.

It really is hard for us to believe, and I say that sincerely, it's not full modesty. It's hard to believe people that you know and are close with.

And respect.

Enormously, would really be listening.

Yeah, no, I listen regularly. I love all of you. And I feel like I need to just get this out at the beginning, because I think this will help me be less nervous. Dax intimidates me. Yeah.

Wait, starting when?

Okay, so Dax has been in my life for, I think, 13 years. The whole ride. Yeah, I've been with Jimmy for 13 years. I knew Kristen before you. We were friends and would go on these girls' dinners and love her.

Wow, that seems counterintuitive. Right.

I feel, and this is going to sound douchey, I don't mean it to sound douchey, but I'm using these in context to compliment you. I'm not starstruck by people. I just came from Howard Stern's home. I've had Oprah over for dinner. I've had Diane Sawyer in my home.

Rihanna in your bed.

Yeah, Rihanna's been in my bed. I've had an intimate dinner with Paul McCartney. I've gone to the White House. None of those things. scare me.

I find that, as you might imagine, almost impossible to believe. And I don't want to intimidate you, yet. I'm also very flattered by that, for whatever reason.

And I was trying to figure it out, and I was talking to you, and I'm like, I don't know what it is. I really didn't come here just to compliment Dax, okay? I won't allow that to go on for another five minutes. I'm not here just to blow smoke up Dax's ass. But I think it's because you are an anomaly of a human.

Okay, so maybe it's just the unsettling.

You have to stop. Be more of a stereotype.

Pick a lane.

I think it's also because you talk to so many people, and you know so much. I think you're incredibly intelligent, both of you, and you're both very emotionally evolved humans. And so when I'm around you, I almost think like, what could I have to offer? or something? I don't know.

Yeah, for backstory, she said, can we chat tomorrow? And I was like, of course, but I wasn't expecting that. I said to my friend, I said, if she is calling to say she doesn't think she's quote, worthy of being on this show, I'm gonna freak out.

You're gonna really let her have it.

Yeah, I'm gonna yell at her, which is exactly what happened.

And to be clear, I didn't think you were nervous. I didn't detect nervousness. I knew this from Monica, obviously.

I told your secret.

Good, I'm not nervous. Like, ask me a question. I'm not nervous to answer. It's more of, especially because I hold you guys and this podcast in such high regard, and all the experts are like, psychologists, pathologists, marine biologists. And then I'm coming on here as a comedy writer and producer, and I think, wow.

But hold on a second, Molly. I gotta push back on your story about yourself. Okay. There have been, since you and I were alive, I'm guessing, but probably seven late night talk shows that have run for more than five years. Yes, that sounds about right.

Well, thank you, I'll take the compliment.

Because we both love Letterman. Yes. And revere it. And I know as a kid, you revered Carson. Imagine how excited you would be to talk to the head writer of Johnny Carson and ask, what was that ride like?

Completely. You're absolutely right.

In fact, I think you know the Letterman writer, don't you?

I kind of know all the writers on the late night shows and have a lot of respect for all of them.

In your world, is there one that you're like, oh, that person was?

Well, I have a lot of respect for Meryl Marko and what she did at Letterman. I think she's exceptional. But I have truly respect for any comedy writer who can succeed. I think comedy traditionally, and now that we're producing the Oscars in particular, I think comedy isn't taken as seriously as drama. And I think it's just as hard, if not harder, to make someone laugh.

There's no tricks. We can't add the perfect song or the perfect push-in to get the emotion we want.

Completely. I have such a respect for comedy writers. And I'm very grateful for all the ones who came before me, especially the women. Seeing Tina Fey and Amy Poehler the other night on the Emmys, I was losing my mind because I feel like those women paved the way for a lot of women.

I'm inspired by them as a man and have been from the get.

And they're still so good. That was the thing. They're still the best.

They really are. I didn't want them to go away. I know.

I keep them up there. You think the X factor with them as well is it's like, A, they are great performers. They are also incredible writers, both of them. But I think that what trumps all that is that, at least seemingly, they have a total rejection of worrying about whether men are going to approve. They seem isolated in the way that Taylor Swift does.

And yet they remain very approachable and relatable, especially then as they became mothers, using that in their comedy and then the movies they produced. I have such respect for them.

Well, here's a question. So, as all these people have cycled through the show, and again, to your point, you've had all these different people in your house and on your vacations, but beyond that, you've been there for what now? 15 years? How long have you been there?

I started there midway through season one, 20 years ago, as the assistant to the executive producer.

Okay, so 20 years, let's say 200 shows a year, two guests a night, that's 400 times 20.. I don't know what that is. You've seen several thousand actors come through. Yes. Do you find that you're more intimidated around the women?

I do. It's weird. I'm not that intimidated by that many people. Right. Just you.

Just the one.

So now I'm paranoid. it's going to wear off. No, no. I got to add something to the-.

No, it will not wear off. I'll always hold you in high regard. I'm going to work on my intimidation because I don't want to be intimidated by you.

I think it works for us.

Yeah, I think so. It's working. I think the job has helped me not be intimidated by celebrities. I just see them as people doing a job. I tend to be more intimidated by people who write, who do the work behind, because I know how hard it is.

Okay, this will sound super self-indulgent, but I do think maybe there's something at the bottom of this. Is it possible, because I have had this, so when I've been in these same circles you've been in, generally I'm like, well, this person's career is much better than mine. This person's more famous than I am. This person has more money than me. I'm now looking in my head, I'm like, but I can fix cars.

Yes.

Right. I do. That you go, yeah, but I'm a real person, and I know it, and these people have a little bit floated off into the ether.

Definitely.

And then, when you meet me, you're like, this dude's still kinda in the dirt. Yes. Could that maybe be what's happening?

No, 100%. No. No, I think you might be right, because it is. It's like, you feel like a family member to me. When I watch the way you and Kristen raise your children, I admire you guys so much.

Let's go to Missouri. Okay. Okay, 1978?. Yes. Okay, now I've met your parents, and I've met your sister.

She's the best. I am so lucky, I have the greatest sister ever.

What a party. You guys could be like the characters in a coming of age thing.

Yes.

What are mom and dad like? What is home life like? Where are you, rural, city, suburb?

Suburbs of St. Louis, mid to low income family. Grew up going to Catholic schools, kindergarten through senior of high school. Wore a uniform, super conservative Catholic upbringing. No boys in my high school, which I loved, and I credit to this day for the confidence I had to be in a mostly male, dominated writer's room.

Interesting, because you hadn't developed any of the bad habits.

I didn't care what boys thought about me, and I think I really cared about the girls at my school thinking I was nice and funny and talented, and I ran for student council and won those elections, and that's all I cared about was female approval.

You and Monica, to me, have some very shared qualities. Ooh, that's flattering. Well, you both should be flattered. you're both dynamic. You're like a bit type A and pretty on it.

I'm a Pisces. She's a virgin. I was a virgin until 24.. No! Oh yeah, that's the other part I'm not bringing.

Wow, that is a crossword.

Oh yeah.

I had no idea.

Oh, I was dry, humping well through college,

denim on denim. Because you weren't supposed to?

I thought it was bad, you're supposed to save it for marriage. I also thought alcohol was bad, I didn't drink until I was 20 years old. Wow. I would drive all my friends around high school, they would all be drunk in my mom's minivan and I would drive them. I didn't judge what they were doing, but I was never gonna participate in it.

Wait, is it working for him? Because I have a fantasy that at like 70, I can start buying him beers.

It kind of is. And weirdly, Jimmy encourages it in our home.

Oh God.

I had never seen my dad. The last time I saw my dad drink, I was in second grade. And then he came out to visit me and Jimmy, and he's like, I'd like to have a beer. I thought he was kidding. And then Jimmy looked at me, like, what do we do?

I've just learned of this through my therapist that there, like, are many people who have had long-term sobriety and then in their older life have. That's an anthem in AA. That's supposed to not exist. So I've just like, kind of been.

Interesting.

Maybe you can try it at 75..

We see where this is going.

Don't dip your toe in the ice next week. He's like, I'm turning 50 soon, so I should try it again.

No, I'm not building a case for myself to do it. I'm just saying that I was kind of given a singular view of how it works. It's been pointed out to me that some people do.

Okay, well, it might be a war giver with my dad. I don't know. I grew up, he was sober. He would read from the AA book at night.

So he went to meetings?

Yes, I went to Al-Anon as a kid. Oh, wow.

Oh, yeah. So you remember when he was not sober?

I remember witnessing him drunk when I was in first or second grade. And I remember my mom calling the police on him because he was trying to leave the house driving. And I remember watching the police come talk my dad into not driving. And that was very scarring. Shortly after that, he started going to meetings.

Why?

I just remember, like, stop it. Like, he just loved to talk about his sobriety and I found it so annoying.

Why haven't you and I bonded over this? Because you know, my dad was sober too. Yes. I too had to go to Allotine.

Oh yeah, I went to Allotine.

And then I was like, this isn't for me. I'd rather be with other people. So then I would go to AA, meaning I had never drank. But I wonder, so some of it was this Catholic thing. Maybe the virginity.

Yeah, I think I thought it could be in my genetics. If he could do it, I could do it. I was very afraid of it. I remember my dad saying, an alcoholic is when you get drunk, you make mistakes and then you want to do it again. And you change the way you behave so dramatically that you're not yourself anymore.

So you were really susceptible to feeling bad and beating yourself up. Yes, very. Where do you think that comes from? Is it genetic?

I would say it's my upbringing. My dad scared me so much, alcohol and sex. Oh God, my parents both would try to talk to me about sex all the time. They went to drive me to college. Now, keep in mind, I'm still a virgin going to college, driving from St.

And was their baseline fear level just a bit high about life in general?

No, not worriers at all. I had a broken arm for six days as a kid. My parents never took me to the hospital.

Well, that could be laziness coupled with.

Yeah, probably also just laziness or finances. But they were not worriers by nature. Never locked our doors. They weren't scared of other things. It was those two.

And with a boyfriend? Oh, of course, with a boyfriend. Well, sometimes it goes the opposite way. You're waiting, waiting, waiting. You're with this person.

This was a boyfriend. It was to a Nora Jones CD.

Oh, beautiful.

What song? We love her. We were listening to the whole album.

Sunrise.

By the way, it wasn't even the first Nora Jones album. It was the second Nora Jones album. That's how long. Don't know why I didn't come.

I used to come in my den.

No, no, don't do that to her.

Oh, my God, wait. When you had sex with him, did you feel like, well, I guess I have to marry him?

I thought for sure I was going to marry him.

So let's have sex now. And you did, that was Jimmy.

Yeah, that was Jimmy. No, I did not. I did not marry him. I'm very glad I did not. Dated a few other people and then had a lot of fun dating.

It's even the PG version of fucking casual sex. Couldn't say it. Couldn't say one night stand.

Oh God, no. But I did have a few of those. And yeah, then had a great, healthy, fun dating life. And then, I'm sorry, I don't want to take over your interview. I was just going on.

What are you talking about? This is exactly how it works.

So then I dated a lot of different people. I hit the improv community in LA. Met a lot of guys there.

They move fast and loose in that circle.

What was your circle, UCB?

I did Second City in Chicago. I graduated from there. Then came out here, did ImprovOlympic for several years.

IO, as they say.

Oh yes, IO West. And one time was dating a guy who I broke up with, and I swear to God, he did scene work when I broke up with him. So I break up with him. We'd been dating for a little while. I said, hey, I don't really see this working.

I don't know if he's a genius or psychotic. Maybe a little of both.

That's the cringiest thing I've ever heard.

Breaking up with an improviser and he's doing scene work.

Space work.

Space work, yep. Ew. Yeah, that was rough.

He took out earplugs and put them in.

And he like thought. maybe that would make him hot again.

Yeah, I think so. I think he was hoping that would work.

I'd pay a fortune to see a closed circuit recording of that.

To me too.

Oh boy. Okay, but before we were at IO and before we were at Second City, we're back in Missouri. How do you say Missouri?

Missouri, I hate Missouri.

But people do say Missouri, right?

Yeah, in some parts.

Monica hates it too, because sometimes I do it. Because it sounds like. Placating, pandering.

I just hate it.

You just hate it. I hate it too, yeah.

Because it's just not right. No, it's not right. And you know it's not right.

It's one thing if you just don't know and you're messing up, but when you know.

No, no, I know.

It's not you, the general you. You included.

Okay, the ambiguous you. The informal you. Yeah. Do you say Appalachia or Appalachia?

Appalachia.

But see, don't you think, when they tell you how they want you to say it, like. we said Oregon, growing up in Michigan, but then I learned it's Oregon. Everyone in Michigan says Oregon, the Oregon Trail.

How do you say the state Las Vegas is in?

Oh, Nevada. Is that correct or incorrect? Yeah, that's correct. According to Jimmy.

I've said Nevada and Jimmy, yeah. And now, every time I say it, I think of the word dad, and I'm like, Nevada. Because he has corrected me so many times.

It's hugely important.

Very, very.

Okay, so one question of mine was answered, which is my hunch was you were popular because you're a social butterfly. You're so very assertive.

I was popular. I was nice. I remember the boys in grade school saying I was the nicest girl in the class. And I took that as an insult. a little bit.

Did you have any class clown in you? Or were you pretty well behaved in class?

Rule follower. You know, I liked an impression of the gym coach in front of the school. I had my little funny moments, but I was a very much rule follower, good student.

And you went to Kansas State? What do we call it? Kansas City?

KU. Lawrence, Kansas. I'm so sorry. Totally different. Okay.

Kansas University. KU.

He doesn't understand. when you mess up colleges, it can hurt. I know.

Yes, of course. Sometimes it can really hurt. The reason I was confused, and I blame Kansas, the city. Kansas City's in Missouri, and it's in Kansas.

It's so confusing.

So I just went, well, she's from Missouri, she went to Kansas, that has to be fucking, I don't know. That makes sense.

I was at the University of Kansas in Lawrence, four hours outside of St. Louis. Journalism major, because they had one of the best journalism programs in the country.

Yeah, so you were gonna be Diane Sawyer.

All I wanted to be was Diane Sawyer. What a bombshell. What a bombshell. When I was a kid, I wanted to be Diane Sawyer. I used to go around my neighborhood with a camcorder and pretend, and be like, I'm Diane Sawyer.

Oh, I was in love.

Oh, my God.

She was everything you want.

She was the daughter of an alcoholic. It's all I wanted.

By the way, you would have worked for Kristen's father. Oh my gosh. Do you know this? He was a news director in St. Louis, and maybe even that channel.

Oh, I should have done it all differently. I do an internship in St. Louis at this local news channel. I shadow this woman all day. I cannot, for the life of me, remember her name.

I'm like, yes, maybe, I don't know.

I thought I did. And then I changed my career path that next semester. I said, forget it. I'm going to do advertising and I'm going to write creative. And then my dream job was to work for like Leo Burnett and write a Coke commercial.

But you know what's so interesting is, at first glance, I'm like, what a terrible thing for that woman to do. And then I go, well, I'm really glad she did that. These things that you think would be implicitly right or wrong are not. You just end up somewhere and you're either delighted you did or you didn't. But weirdly, I'm grateful that you were so accepting of her advice.

I am grateful I was. I'm very impressionable. I will get a bad haircut anytime. Because if I go in and someone goes, you should have bangs. I'm like, well, they know more than I do.

What was that teacher's name? Let's shout them out.

That was Mrs. Cooper. God bless her. Best teacher ever. And she went to my parents and said, your daughter's a good writer and she's going to be a good writer.

Mine was Larry LeClaire, seventh grade.

Oh, I love Larry. What did he tell you?

You're an incredible writer. I'm going to put this thing you wrote in our annual, they put out a magazine, you know, like a shitty Monica Sina. It's paper. It was Xeroxed. It was like the Muir, or whatever the fuck it was called.

But didn't he also put you in the math?

That was, Mr. Wood.

The weight of people's words with children is so important. But here's the thing. Do you find with your kids? So that, being my past, and my parents always believed in me. My dad told me on a regular basis, you could be president of the United States.

You might. Well, given the competition, I do too. Yeah, right.

Hey guys, anything's possible. But I do think that just telling kids things helps them believe it. It becomes a reality. But do you ever worry about doing it too much? Because I find I'm constantly complimenting my kids.

I have a policy. And it's already evident in the story you and I both told. You already wrote something that your third grade teacher read. I had written something Larry LeClair read. I think a lot of people tell their kids you're great at shit.

I think it also depends. A compliment from a non-parent for me meant so much more. Any compliment from a parent, I just didn't even hear.

Isn't that sad though?

As a parent it's horrible. Yeah, as a parent, I'm like,

I know her better than anyone. My compliment should mean something.

It feels good to me, because I'm not a parent and I can just hand out compliments. Yeah.

Yeah, but I'm like dealing with all the temper tantrums and the bullshit. Right. I feel like I've earned that. But yeah, I think it's greatly reduced. Unless I think I'm doing my research last night, for Rob Reiner and his father did the thing he wanted to do.

I agree with that.

Stay tuned for more Armchair Expert. If you dare.

I love Lil Dicky.

Dave Byrd.

That is one of the best shows ever.

I'm so excited for Monica. She hasn't watched it.

Oh, I'm so jealous. you get to watch all that. It's fantastic.

I'd give anything to erase my memory and do it all over again.

Me too, that and Breaking Bad, take me back.

Take me back. But he was working similar to you as well. He's like, well, marketing's creative and safe.

Completely, because when you're a kid in St. Louis, you don't know that's a possibility. I remember when I was, I'd say about my daughter's age, like eight, nine years old, and I'd pretend to do commercials. Like my mom would make me cereal and then I would pour the cereal in the bowl and I'd hold it up and pretend and I'd do little commercials. And then I remember her saying to me, do you wanna be an actor?

This got so personal for her.

Yeah, and then I said, and I remember thinking, yes, I could easily do that. But I said, no, of course not. I couldn't do that. And then that's kind of where the acting dream died. Oh, my God.

You've been diverted in so many directions in your life.

So many directions. You could have been so many things. Yeah, a lot of people talking me out of stuff, talking me out of my dreams.

But I agree with you. In a suburb of Detroit and Michigan, weirdly, I thought it was more probable I could be the president than an actor.

Absolutely.

There's a path you take, it's kind of laid out.

And I think kids need to see and know local stories. I'm really grateful. John Hamm is from St. Louis, because people now know, oh, maybe it's possible for me. And Ellie Kemper's from St.

Molly's from St. Louis.

Molly's from St. Louis. But I think it's important that we celebrate the local stories so kids see themselves. I remember, I loved Johnny Carson so much and I watched it every night. It never even occurred to me people were writing that.

And you said, your mother too still refuses to accept that. Jimmy's not just coming up with everything?

Oh, yes. It's like, oh, he was so great. That thing he said and that thing he did, I'm like, yeah, I know, I wrote it. Who says that?

Her mom still is under the illusion as she was watching Carson, like, oh, he's just off the dome he is.

I also love when people, the thing about writing for a late night show is that everyone thinks they've got an anecdote for you that makes sense. Like, oh, they'll tell you a crazy story about their dishwasher breaking. Like, you got to put that on the show. No, I don't, no, I don't.

Yeah, I've heard a lot of movie ideas over the years.

Oh, I bet. Sometimes it's like, have you thought about having Julia Roberts on?

Oh, no, oh, no, never thought of it.

Well, that's a good idea.

Definitely haven't.

We had been saying no to her, but now I think we might say yes.

We're gonna bump Molly, we're gonna bring in Julia.

I sometimes respond to the people that are like, please get so-and-so on. I'm like, we've invited them a hundred, like, you think. we're not inviting this person on? Of course we are.

That's all you're doing. Yeah.

Literally all we're doing.

So you actually find employment, though, in the advertising business?

I worked in ad sales in Chicago. I love Chicago, moved there after college. Was in ad sales, which still wasn't in the creative part, right? But man, it was easy and lucrative, and I got to work like three hours a day and had an expense account. Oh, baby.

So exciting. To be young and have an expense account, what could be hotter than that?

And I worked for a music label or for Interscope Records, and so I got to go to all these concerts and just take clients to concerts.

AKA friends.

Yeah, exactly, exactly. One client, six friends. But it wasn't creative enough for me and I wasn't happy with it.

Were you doing Second City then, while you had that job?

Yes, I discovered Second City while I had that job. Even in Chicago, I thought, okay, I like performing, I like writing, I like doing all this, but I gotta get into Leo Burnett and write Coke commercials. That's the only way I thought that could translate. And then Interscope moved me to Los Angeles to do sales out here. And while doing that, again, great job, making great money, a friend of a friend said, there's a job opening at Jimmy Kimmel Live to be an assistant to the executive producer.

This was just a huge quote step down.

Yeah, I was making about a third of the money I was making. I was working about five times the hours. This is when Jimmy Kimmel Live was actually live. So we would shoot the show from nine to 10 p.m., Monday through Friday. It was the longest work day ever.

Yeah, you know, it's funny. I have a great friend, Andrew Panay. He's a producer. He's done a bunch of movies. We've done a bunch together.

It's really great.

Back to Second City, though, did you have any folks in the program at that time that ended up being?

Yes, I remember a young Bill Hader.

No way.

I remember watching Bill Hader and thinking that guy is incredible. Jack McBrayer.

Sweet, Jack McBrayer.

I watched some of these guys at IO West and thought like they have something special, I hope. And I remember thinking, I bet I could try to get them on Jimmy Kimmel Live. I used to take a lot of improvisers and put them in bits. There's so many great comedy actors who've come out of improv, as you know.

Don't you love, because I have that with the Groundlings. I was in the program with so many people for years and then I watched them pop up at different times. And there's something that feels so special about being connected to it in the most beautiful and sincere way, which is when you've seen the innocent beginning, and it pays off.

You've been in bad scenes with these people. Yes, yes. You've seen them tank and then you watch them grow. It's fantastic. I find that community very encouraging, the improv community.

It is, yeah. It's such a shared experience. Like you all live or you all die together.

Yeah.

Okay, great. This is one of my questions about the mechanics and how the sausage of the show is made. I wonder, with you in the writer's room and how you guys all work, how are you policing yourself or evaluating if it's esoteric and inside and for each other or if it's for America?

That's a great question. And I will say it's difficult if we have a writer or someone on the staff in a bit. So like a lot of times, we'll cast people at the show and stuff and it gets a huge laugh for rehearsal. And we have to say, is that just because we all know Becky? Yeah.

How many staff writers are doing this? The 5 a.m. person.

Shout out to Nick.

What up, Nick? Big props. How many stories does he give before it gets whittled down?

He'll give about 11 to 12 stories. We narrow it down to about six to eight stories, I would say.

Okay, great. So the 19 writers get six to eight stories. Then they write two pages on that.

And now Jimmy gets a thick 50 page document. He whittles it down to about five pages. That's sent to us by 10 a.m. So now we have a pretty clear understanding of what our monologue's going to be. Then we all start writing more jokes.

Oh, the pace is so awesome.

You're writing it, you're rewriting it, you're having the head writers punch up on it. Then Jimmy always does a punch up. And then you shoot it, you edit it, you are oftentimes racing it to air our shows at 4.30.. By the time you've been assigned to, you're gonna do this bit, it's 10 a.m. And hopefully it gets approved and it's ready for air by 4 p.m.

So it's been filmed, edited, everything scored.

Yes, it is a rush. What a pace. It's incredible, it's insane. It's interesting, though, because the victory of getting that is so great. But if it tanks, ooh, it hurts.

Because you worked so fucking hard.

You worked so hard, you spent your whole day, you haven't eaten, you're like, did I even drink water today? But the other side of it is that those failures are very short-lived, because time to go tomorrow, gotta do it again. And I will say it's changed significantly late night, at least for us in the last few years, because I think of the 24-hour news cycle, things are moving so quickly. And particularly when Trump was president, he would say something outlandish at 3 p.m. Oftentimes we scrapped our monologue and rewrote it entirely.

We wrestle with this a little bit. Is it insane to not acknowledge something versus? is it our job to acknowledge that thing?

I think it's very hard. And I find that a lot of times. I think, how are we not talking about this thing right now? But if you talk about everything, nothing matters anymore. I think you have to find the things that are really meaningful for you, particularly for Jimmy and I.

A thousand percent, you really have to pick your battles. I'd imagine too, you also have to remind yourself what you do. I fall back on, I credit Stern in many ways to being brave and not talking about Trump and getting a lot of heat for not doing so and having the position of like, you can hear about Trump anywhere. You deserve a break from Trump. That's what this show is.

I think that's one of the reasons I'm drawn to your podcast is because it is an escape from that.

We need a fucking break.

Absolutely.

So yeah, you guys are really like walking this precarious tightrope of you. do do topical stuff. Right.

The goal of late night, the monologue is for a host to feel like it's like you're talking to a friend about the day and what happened today. When Trump is dominating the news cycle, that's all that's being ingested all day. And then our job is to talk about the stuff that's being talked about, but it is just like a never ending cycle. The other element for us is Jimmy always says, I don't want to normalize the behaviors of things going on right now, both sides. So it's like, if people are leaning towards a dictatorship or leaning towards everyone needs to be canceled or whatever, we can't normalize these behaviors.

I appreciate that, because it's actually quite misleading. The tail has been wagging the dog in that those two viewpoints you just illustrated are really 5% marginal viewpoints that somehow drive the entire narrative of all the mainstream. And so, yeah, you do have some, I think, obligation to not be reporting on what the 4% of the country actually thinks about. It's hard to know, though. It's hard to delineate.

It is really hard. And especially when you turn on the TV. and that's all that's on the TV. It's so interesting how dramatically our monologues have changed. I remember for two or three years, it was like American Idol was our number one news story every night.

I know. And there's this like call to constantly get into it. But I also think you actually have to fight back from it. You have to keep it proportional. It's hard.

It's funny because, Jimmy, we're always at this balance. Like we have to talk about this, and also it's like, guys, is there anything else to talk about? It's like we say both of those things every week. It's confusing.

I forget what TV show I was watching, but it's an English show. And the person said, this season of America is boring. They were talking about like first two years of Biden being around. I was like. That's funny.

That's funny.

So I think people would be similarly misled as I was. And of course, egocentrically, I thought the guests were a really big deal. But I think I've talked to Jimmy enough times where he said like, the guests really are the second. The show's the monologue. Could you like explain that to us?

Well, yeah, the monologue is the highest rated portion of the show.

That surprised me. I'm embarrassed to say that.

Yeah, that's all right. It also could be the fact that it's the first part of the show and people are starting to fall asleep. But people do. also, the online numbers is the monologue. It's incredible.

I think that's what Phelan's been really, really smart about. Definitely. Jimmy somehow gets them all to do the most insane things.

Yes, for sure. Our big viral video, when was it, 15 years ago? The fucking Matt Damon video really changed the way, did you get excited when I said Matt Damon? A little bit, just a little. And fuck.

My client wants to win the lottery on Wednesday.

But that really, I think, got us in a space for doing more interesting things with guests and people trust us to now make these funny videos.

Well, Jimmy hated this when I insisted on him acknowledging this, is that, very much like Dave had invented some staples in late night, crazy pet tricks and these letters and the top 10.. You guys did that too. The notion of the viral video emanating from a late night show didn't exist yet.

Yeah, I guess you're right.

And it's been regularly copied. So it's like, you guys invented a thing that will probably stay with this format forever, or as long as it lasts.

So how do we get from assistant?

Oh, okay.

Can I ask one more question about how the sausage is made first? Absolutely. It's just the button I wanna put on the trying to police yourself and know what is gonna be inside baseball and not. My other curiosity is like, how do you even evaluate it? Because I have been to that show now.

That's a really good question. Because first I'd say, oh, you can feel it in the room. But there are oftentimes you get a bad audience.

Exactly. I've left there thinking I shit the bed this time. And then I'll watch it with Kristen on the DVR. And she's like, wow, that was one of your best.

Yeah, because sometimes you have an audience that is there to see you. So we'll have 30 Dax Shepard fans in the audience and literally just following you. Then there are other nights that it's a bunch of people on vacation on Hollywood Boulevard and we pull them out of the Wetzel's Pretzels.

Half of them are German.

Yeah, exactly. The studio audience is not as telling, I think, sometimes. And oftentimes, especially when you have international audiences, might not understand a local joke, if that is brutal. I hate to say the internet kind of is the judge, but I do think when things do well online.

Because you can track the views. That seems like a very good barometer. Right.

And with our bits we love, we're like, no one's watching this online. Like you separate them out. It's like, no one's watching that one. And then you're surprised sometimes at the one people are drawn to. And so you try to repeat those more.

How are you even here today?

I'm not. I'm at the doctor.

I feel bad. we took, I mean.

Well, I'm going back and forth right now between Jimmy Kimmel Live and the Oscars offices. right now. I'm more now in Oscar production. I've not stepped away. I'm still at Jimmy Kimmel Live, but definitely part-time right now, while I'm producing the Oscars.

Too much. Okay, no, I'm sorry. I had interrupted.

I just have so many questions. How do you have a family when you're a staff writer there? That seems impossible.

I think it actually is kind of impossible. I'll be honest with you. I think it's why there are not a ton of mothers in a writer's room. I think it is a very challenging job in a late night writer's room. I'm one of two moms in the room, but we have a lot of dads in the room.

The schedule you just laid out.

I need to squeeze this in now. I feel really bad. we invited you. I know, that's what I'm saying. Let's go.

I'm so happy to be here. And, by the way, I'm totally relaxed and I'm not nervous anymore. Just want you to know that. It is definitely a grind. The morning routine with kids is tough because I find myself, I'm looking at the news, but I'm also trying to pack their lunches and be present with them.

You need those glasses that spell our dystopian future, where you're looking at all the news feeds but staring at your kids and they think you're looking at, that was one of that Apple commercial. I'm like, this is a positive? Right. This seems terrible.

Make eye contact.

Yeah, Monica's a great question. How does one start getting coffee and then end up as the head writer?

Okay, so I was executive producer's assistant. I immediately knew, oh, I want to be in that writer's room. Steve O'Donnell was the head writer at the time. He's the guy who created the top 10 list at Letterman. Brilliant writer.

On the custodial staff.

Yeah, I would do anything. And about six months later, the executive producer left the show. I thought, oh, I'm done, but they kept me there.

The one you had been assisting.

Yes, the one I'd been assisting, Daniel Kellison.

Because he wasn't at any of his appointments and his whole schedule was fucked up. Yeah, right, right, he was doing podcasts.

in the middle of the day. Yeah.

Right, totally. So he left. Then they moved me into the segment department. The segment department are the ones that do all the interviews. They each are assigned to a guest to research and produce.

Shout out Josh. Shout out Josh. He's always my guy.

He's so good.

He's so fucking good. I was just thinking this morning, I was like, Josh gives me a phone call. I don't know what I'm gonna talk about. And he can steer me into all these stories I didn't know. I'm like, he should have a podcast.

Yeah, he's incredible. He's really good. I appreciate that shout out, by the way. It's nice when people appreciate the work people do.

I value him like crazy. Because other shows, I'm like, I gotta come in with about 16 stories. And I really have gotten to the point with him where it's like, all I gotta do is hop on the phone with Josh and I'm gonna leave with four or five stories. Yes. And that's all him.

Because I would imagine you wanna save your stories for your podcast. I know that a lot of actors will keep like a little notes app on their phone. Like they'll keep a story in there for their late night or for their press. What do you do now?

I don't ever think about, thank God, filling content on this show. When Monica and I sit down and do a fact check, I think it's Monica. Like she and I have such a bizarre creative chemistry. Because when I do other shows without her, I do like, I gotta go in with a few stories to tell. But with Monica, I sit down and I'm like, well, until Rob turns the mics off, we could shoot the shit.

Yeah, it feels that way as a listener too. It just feels organic. Like you're listening on someone's conversation, which is nice.

Yeah, so I don't really ever think about saving anything for here. And I don't worry terribly. if I've said something here and I say it on your show. I'm assuming there's minimal overlap. I don't know, maybe I'm wrong.

Well, if there is, let me assure you that someone's being told that at the show. Seriously, there's a whole team of people that when a guest is coming on, do all the research. And then if you're up there and you're telling a story, there'll be like a pinch. and I'm like, he told that on the podcast. And I always feel bad.

And, by the way, it never looks bad to the show. in my opinion. It looks bad for the person who's telling the story for the eighth time and eighth place.

They don't have anything else to say.

And in fact, we never run into trouble. It's only an asset that Monica doesn't research because she is the police about when I've gotten too esoteric with the guests and I'm assuming people know stuff that wouldn't be known. That's like a vital role. It's imperative. she doesn't do the research.

I love that, though. That's a good dynamic. to have both of those. That's really smart.

Yeah, so, I don't know what the fuck we were talking about there. Oh, we were talking about- Produce it, produce it, produce it. We were talking about how I'm presenting a producer to now.

So then I went into the segment department for a while and season one, two, three, basically through the Matt Damon video, no joke, there would be a Tuesday where we would not have a guest. Our music was always booked and we had great musicians, because everyone's trying to push these albums and there's these deals with the studios paying for this great performance. We always had music. Be it Tuesday, we're like, okay, it's three o'clock, we don't have a guest. So I would go over with a clipboard over to the Roseville Hotel, to the musical guests' hotel room, and I would start interviewing them, because I'm like, you're gonna be interviewed now, we're moving you up.

I would say half of my appearances on the show have been like someone fell out.

We're like, hey, Tuesday at three, 100%. Thank you very much for your service. I started interviewing musicians and producing their segments. I remember week one, I did 50 Cent, Carole King, and Slipknot.

Whoa.

Walked over there, interviewed them, then I'd go over to Jimmy and say, here's how you're gonna interview them, here's some good stories. So I started there. I loved producing, it was great writing the guest segments, but I really wanted to be writing the comedy. So Steve O'Donnell called me up about two years into being there and he said, I have a spot as a writer's assistant, would you like it? And I was ecstatic.