Switched on Pop - What do John C. Reilly and Taylor Swift have in common? The Great American Songbook

Episode Date: October 14, 2025

John C. Reilly joins to discuss Mr. Romantic, his theatrical tribute to the Great American Songbook that treats Irving Berlin and Tom Waits as equals in the canon of timeless American song. Reilly recorded live in one room with his band using vintage ribbon microphones, embracing the squeaks and imperfections while layering in cinematic sound effects—crickets outside a lover's window, a collect call from prison—to transform each standard into an immersive scene. But what makes a song from the 1920s feel eternal? Music data scientist Chris Dalla Riva, author of the forthcoming Uncharted Territory and the newsletter Can't Get Much Higher, breaks down how composers like the Gershwins wrote for amateur musicians playing sheet music at home, creating universal lyrics and AABA structures where the hook comes first. That accessibility is precisely what draws Reilly to this repertoire. He sees himself in the lineage of interpreters like Sinatra, not selling his own story but passing along music that already belongs to all of us, like holding up a seashell and saying, "Isn't this one beautiful?" More Get Chris Dalla Riva's book Uncharted Territory: What Numbers Tell Us about the Biggest Hit Songs and Ourselves Subscribe to Chris Dalla Riva's Can't Get Much Higher Songs Discussed Taylor Swift "The Last Great American Dynasty" George Gershwin "I Got Rhythm" Village People "Y.M.C.A." Billie Eilish "Bad Guy" Frank Sinatra "On the Sunny Side of the Street" Judy Garland "Over the Rainbow" Ella Fitzgerald "My Romance" George Gershwin "But Not for Me" Elvis Presley "Are You Lonesome Tonight" The Beatles "We Can Work It Out" The Beatles "Get Back" The Beatles "Yesterday" John C. Reilly "Moonlight Serenade" John C. Reilly "Dreams" John C. Reilly "Johnsburg, Illinois" John C. Reilly "Falling in Love Again" John C. Reilly "What'll I Do" John C. Reilly "Picture in a Frame" John C. Reilly "Just Another Sucker on the Vine" Randy Newman "Ragtime" John C. Reilly & David Garza "What's Not To Love" Harry Nilsson "Coconut" Judy Garland "Somewhere Over the Rainbow" Dooley Wilson "As Time Goes By" The New Vaudeville Band "Winchester Cathedral" Andy Williams "The Days of Wine and Roses" Nat King Cole "The Frim Fram Sauce" Learn more about your ad choices. Visit podcastchoices.com/adchoices

Support for this show comes from Odu. Running a business is hard enough, so why make it harder with a dozen different apps that don't talk to each other? Introducing Odu, it's the only business software you'll ever need. It's an all-in-one fully integrated platform that makes your work easier, CRM, accounting, inventory, e-commerce, and more. And the best part, O-Doo replaces multiple expensive platforms for a fraction of the cost. That's why over thousands of businesses have made.

made the switch. So why not you? Try Odu for free at Odu.com. That's ODOO.com. Welcome to Switch Switch John Pop. I'm musicologist Nate Sloan. I'm songwriter Charlie Harding. Charlie, last week, we talked more than anybody could possibly want about Taylor Swift's latest release, Life of a Showgirl. And I think one of the really cool Easter eggs that we uncovered is that there is a showgirl sound on this record. Right. The sound of the 1920s, the sound of composers like Irving Berlin, of performers like Ethel Merman. And really, we never said this out loud, Charlie, but it's the sound of what we would call the Great American Songbook.

Taylor Swift, of course, wrote the Last Great American Dynasty. Surely she must appreciate the Great American Songbook. So inspired by our muse, Taylor, I want to dedicate this episode to exploring the legacy of this repertoire from the golden age of American popular music about a century ago and find more ways that these sounds continue to resonate not only through the work of folks like Taylor Swift, but perhaps through some of our greatest entertainers like John C. Riley, who has a whole album devoted to this repertoire called Mr. Romantic. Not only that, a whole persona. So this music is alive and well. And I want to understand it better so we can appreciate these sounds and the way they

continue to influence our modern soundtrack. And in order to do this properly, Charlie, we need to bring in a special guest. Please welcome back to the show, Chris Dallariva. Thanks for having me, my long-awaited return. I'm happy to be here. You last joined us as a witness in the case of the missing key change in popular music, a Joe Treble investigation. You're a brilliant music data scientist who has spent, I don't know how many days of your life now listening to every chart topper in American history, and you have compiled that research into a forthcoming book. Can you tell us what that's called, Chris? Gladly. It's called uncharted territory, what numbers tell us with the biggest hit songs and ourselves. and I wrote it as I spent years, as you said, listening to every number one hit song in history

in the Hot 100 era. So I go from 1958 to 2025, but for parts of the book, I had to go further back into the past and touch on many of these great American songbook topics. All right, Chris, so you're one of our two experts in this conversation. Later, in the second half of the show, we're going to bring in Mr. Romantic John C. Riley himself. But please illuminate us with your expertise. You've had every chart-topping song in history in your ears at this point. Let's start with the basics. What was the Great American Songbook? You know, the Great American songbook is, it's one of those things you hear about and you think that there was just some book actually set down somewhere and all of the great songs are in there. But no, it's not really that.

It's like a loose assemblage of songs that were, I would say, written and recorded and you can dispute the dates between, let's say, the late 1920s and the end of the 1940s. And it's usually associated with songs that we know from songs and movies and songwriters who, I think when you think of old songwriters, these are the songwriters you think of. You think of the Gershwins. You think of Col Porter. You think of Rogers and Hammerstein, Rogers and Hart. And it's just those songs that are most covered and most remembered from that era. So what makes this songbook so great. Is it the material itself? Is it the era in which it was created? Like, where did we get this name, Chris? The important thing is the music's really good. The songs that we call

the Great American Songbook, they are associated with an era, they are associated with a place, they are associated with certain people, and a certain setup in the music industry that doesn't really exist anymore, where you had songwriters plugging songs to labels, artists, and producers, none of that matters if the songs are horrible. And in this case, you know, these are some of the most gorgeous melodies that have ever been set to paper and then pressed on to acetate. Chris, I think that's such an important point about this repertoire. Certainly, we can find iconic performances and recordings of pieces from the great American songbook. Like you mentioned George Gershwin and his brother, Ira Gershwin, who wrote many of the lyrics for his songs.

we can find an incredible recording of Ethel Waters performing this song back in the 1930s. Got music. I got my man who gone. Foundational text. But at the same time, I think what you said is so important, this was a songwriter's genre. As incredible as these recordings we have by people like Ethel Waters are, most of this music was played by everyday people at the pianos in their homes. They would go out, they would buy the sheet music.

to the latest Gershwin hit, they would take it home, and they would sit down at their keyboard, and they would play and sing. I got rhythm. I got music. I got my man who could ask for anything more. And people would gather around the piano, and you would all sing together. I mean, records were a thing. Radio was a thing, but I think what's so cool about this era was this was the way that most people

experience this music was like playing it themselves. Nate, I do have to call you out on an anachronism. Your lovely electric piano would not have been fitting in that time. This has got to be an attitune, upright piano in the home. Okay, okay. Hold on a second. Wait, wait, wait. Let me, uh... Ha ha. Much better. Okay. That's it. Sorry, as you were saying, Chris. Yeah, I think you guys are hitting on two things that are very, very important about this era. The first is, is there are recordings. There is radio. But this is very much emerging from the era of pre-recorded music. And because of that, songs are not as associated with singular artists as they are today. So when the Gershwins would drop whatever banger they put out in the early 1930s, it wasn't like that song was associated with one particular artist. Multiple artists would record these songs at the same time.

And I always try to give, when I talk about this, I try to give a contemporary example. It would be like if you took the lead single from Life of a Showgirl, Taylor Swift puts it out. And immediately, Ariana Grande and Justin Bieber also release a version. This seems so strange where you're like, that's absolutely ridiculous. But that's literally what happened. You would have multiple charting versions of the same record released at once. I think that's a defining feature of the Great American Songbook is it's known for reinterpretation. It's known for you're going to sit at the, you know, the upright in your house playing it.

But if you tune to the radio, maybe you'll hear Ella Fitzgerald singing the song. Maybe you'll hear Frank Sinatra doing it. I think that's a very defining feature of these songs, is that they can be reinterpreted over and over again. And that's part of the reason I think why they still sound so fresh. Well, I love that that you started with I Got Rhythm. That establishes in the world of jazz, the idea of rhythm changes, this chord progression that became the sort of standard place for any group of jazz musicians to jam on. and has been interpreted millions of times your basic chord progression right there. Skipidda-da-da-da-da-da-da-da-da-da-da-da-da.

Flintstones, meet the Flintstones. Anyway, yeah, there's a lot of... YMCA, it's fun to stay at the YMCA. Anyway, yeah, there's a lot of songs that use these rhythm changes, progressions, as they've been known. I'm also having this breakthrough moment realizing, as you're discussing, this music as important to radio, but even more important to sheet music that might be sold for playing in the home, I get why these Great American songs often feel less personal and

more universal. They have to be written for everybody. Songs written by Taylor Swift are mulled over for what's happening in her personal life. But rhythm changes. This is something that we can just do in the home with anybody. Yeah, I think that's a very vital observation to the these songs and part of the reason why they remain such touchstones and so memorable is you had to write a melody that was memorable enough where you know you couldn't pull out your phone and just listen to it whenever you wanted it had to be something that could get stuck in your brain but it also had to have some sort of simplicity such that an amateur musician could perform it in their home and i've heard people theorize you guys probably know more about this than i do that you only get

the hyper complexity of like bebop jazz as recordings become more accessible. Because previously, if you were going to write that down on sheet music, no one was going to be able to hear it or perform it because it was too difficult. Right. There was a simplicity and accessibility to these great American songbook tunes. At the same time, there was a lot of sophistication, especially in terms of the harmony, the rhythm, the melodic choices. I feel like a song that exemplifies both that universal lyric and that sophisticated harmony is on the sunny side of the street by Jimmy McHugh and Dorothy Fields.

Let's listen to a little bit performed by someone you mentioned, Chris, one of the great interpreters of the great American songbook, Frank Sinatra. Just direct your feet to the sunny side of the street. I can't you hear that bitter pot And that happy tune is your step Life can be so sweet On the sunny side of the street Okay, I really get this song now

Being a New Yorker for just a few years Because when you're walking in New York The buildings block out the sun on one side of the street Is this a Timpan Alley song or a Brill building song? This is Tin Pan Alley for sure Yeah, written in New York about New Yorkers. Maybe before they changed the zoning in New York to actually make sure that they allowed enough sun to reach the streets, Charlie. That was the thing.

And another cool aspect about this tune, Chris, is something you write about at length in your book, Uncharted Territory and your incredible blog can't get much higher. The form of these songs from the Great American Songbook is a lot different than what we're used to listening to in the 21st century. Yeah. Taylor Swift was our launching off point here, and I think she's a good comparison here, because even if this record has elements that point back to this great American songbook era, structurally, these songs are very 21st century. They're of this verse chorus form, and that's the form that I think everybody associates with popular songs these days. Pop songs have the big chorus, and everything is sort of building and pointing towards that moment. But when you listen to on the sunny side of the the street or I Got Rhythm or Over the Rainbow by Judy Garland. There isn't really a chorus in a traditional sense. You still have two sections, usually denoted A and B, but these sections really exist on their own where you could play the melody to the verse of Over the Rainbow and you finish that. You don't necessarily feel like you have to go to the B section. Whereas if you listen to

any of those songs on the Taylor Swift album, I mean, these verses are building to the chorus. The other thing with this Great American Songbook is instead of a chorus, usually there's a refrain, which is usually just one lyric at the beginning or the end of the verse. It's usually the title. You know, the verses will start off with on the sunny side of the street. And this Great American Songbook form is dominant for basically the first half of the 20th century. And then it starts to flip in the 1960s. And by the disco era, the verse chorus form is really cemented. And I actually think the Beatles are a good example of a transitional. artist because many of those early records are closer to the great American songbook form than they are of the verse chorus form like we can work it out try to see it my way do I have to keep on talking till I can go while you see it your way but the risk of knowing that I'll know you you have the verse and then the bridge or the B section is the life is very short but there's no time for fussing and fighting That's not a chorus in the same way that Get Back has a chorus. As much as they come from the rock and roll era, I mean, they're also playing show tunes.

Yesterday. That's like, that's throwback. It's not. Yeah. That's another perfect great American songbook song is like that A section, yesterday, All My Troubles Seem so far away. Yesterday. By all my troubles seem so far away.

Now it looks as though they're here to stay. Oh, I believe in yesterday. By the time you get to the end of that section, you don't necessarily have to go to the B section, the why she had to go. They exist sort of on their own. Why she had to go, I don't know she wouldn't say. Whereas, again, when you get to the verse chorus section,

is like these things sort of bleed together, and you're just building to the giant chorus that Taylor Swift has mastered so well. But it's sort of a new thing. And once again, it makes so much sense that if this was music originally thought of to be bought a sheet music and played in the home, it adds up that you would want people to learn

the best part first, that you're immediately hooked into the song. The A part is the dominant part of the song. In verse chorus form, you got to wait 30 seconds, maybe up to one minute before you get to the best part. You've had to grind on the piano and learn all this material. It might be three days into learning a song before you're like, oh, finally, I've arrived. Oh, totally.

I think people underrate how the ways we consume music influence how artists write. You know, if you know everyone's going to be listening to your song in a dance club, you're going to write very different song. And then if you know the way they're going to hear it is by sitting down at the piano and having to play it. like music works in certain places better than it does in others. And we've reported, you've reported that, of course, as streaming instituted the 30-second rule in order to be counted as a play, we've actually seen more people entering with their chorus first, almost hearkening back to the ABA era. Yeah, something that's very different about these great American songbook songs.

And it wasn't on the version you played of I Got Rhythm, but some versions, they heard, there's like an intro, which is just a musical section that sort of leads into everything else. it's never heard again. And many of these great American songbook songs, even something like over the rainbow, there is a written introduction. It's usually left off these days. And it's like half sung,

half spoken. And the explanation that I've heard is that because many of these songs ended up being used in movies or Broadway plays, it would be a little kooky to just break into song where you could have this sort of

slow flowing intro that was half spoken to then transition into the song. The intro, especially with this 30 second streaming role is it's so dead. You know, you don't get the long minute and a half intro before the song kicks in like you did back when these songs were performed on stage. Another reason these songs became such cultural touchstones, I think, is that they are really reflective of the time they were created. And if we go back to on the sunny side of the street, this song was written

on the precipice of the start of the Great Depression. And you can imagine that this optimistic message resonated with people. I mean, we didn't get to it, but the end of the song is like, if I never had a cent, I'd be rich as Rockefeller. Gold dust at my feet on the sunny side of the street.

So Rockefeller was one of the big tycoons of the age, a robber baron, perhaps. The Elon Musk of the, of the 1930s. And comparing yourself to him at a moment when people are forming breadlines on the street is kind of an escapist fantasy

for people in this era. So even though the song sounds kind of light and fantastical, I think it had an important role in that moment in history. But most of these songs, like pop songs throughout the annals of history, are just about love, romance, going out and having a good time. And I think part of the way these songs continue to resonate a century later is just how

beautifully they're constructed. It's not always the message itself. It's just how well they're put together. Let's talk about my romance by Rogers and Heart. And another testament to the legacy of this repertoire is the fact that there's a movie coming out all about the lyricist Lauren's Heart, played by Ethan Hawk. And he had a real gift for creating these indelible phrases like in the song, My Romance. Let's listen to Ella Fitzgerald sing this one.

There's a delicious irony in some of these songs. There's this kind of witty, approach. My Romance is a song about how I don't need anything but you, and he constantly finds these new ways to say it, like, uh, my romance doesn't need a castle rising in Spain, nor will dance to a constantly surprising refrain. A lot of these songs are finding new ways to say, love you in 32 bars. And the invention that requires would force these lyricists to come up with every possible way of expressing that. I totally agree. I mean, there's a cleverness in many of the lyrics to these songs. And that's the fact that there is a dedicated lyricist is also something that has been left in the past. And again, there are outliers. Elton John, Bernie Taupin, Bert Baccarac,

usually worked with a dedicated lyricist. But I think having a dedicated lyricist on many of these songs led to a cleverness in lyrics that is not super common in popular music these days. It's not to say there were no bad lyrics written. Like you said, there's only so many ways you could say, I love you, but there are tons of super quotable lyrics from this era that I think is the result of having someone whose dedicated job was just coming up with phrases to set to music. It's also worth noting that in contemporary times,

the songwriter is next to the performer, often the lowest paid person in the whole room. And the shift towards streaming has moved royalties more towards master recordings and artists, rights holders who own the recording itself. And the share of royalties going to publishing to the songwriters has really suffered in recent years. So I'm not surprised that teams have decided, well, maybe we don't want to have a dedicated lyricist that might eat into some of that songwriting share.

Yeah, I think there are like there are a couple things. going on there that have made that an issue. One is it's always crazy to me that producers, you know, they get points on the back end, but they also get an upfront fee, whereas songwriters really only get paid if you write a hit, right? You know, your labor goes unpaid. I think that's a fact of just how powerful the major record labels are and the leverage that they have. But the songs are still the backbone of the whole thing. So you got to have good songs. And that's one of the powerful experiences you get listening to this repertoire. It's an era where the composer, the songwriter, was elevated. And you would go out and you would buy a song just based on who wrote it.

You know, oh, I got to have the latest Dorothy Fields hit, the latest Cole Porter hit. I don't care who's singing it. Like you said, Chris, tons of different people sing it. Who wrote it? Like, what a thought. I love, there's something very attractive to me about that aspect of that era. There's a great quote from an interview Elvis Costello did with Conan O'Brien on his podcast years ago. And Elvis Costello was talking about how his mother worked in a record shop. And, you know, it must have been in the 40s or 50s or something. And he said people would come in and be like, oh, I'm looking for this song. And she would recommend a rendition of the song rather than like, oh, I'm looking for music by this artist.

People were looking for a specific song. It just seems like such an alien world to where we live now where I could just. Shazam, whatever it is, and I could find a specific rendition rather than thinking about the underlying composition. There's a magic and aura and alchemy to this repertoire. That's the reason that Taylor Swift conjures it on Life of a Showgirl. And it's the reason why artists like John C. Riley are drawn to this repertoire. Chris, thanks so much for joining us today. We can't recommend enough signing up for Chris's substack, can't get much higher. And definitely go pick up a copy of his book, Uncharted Territory. If you're listening to

this podcast, you're a music nerd, and this book is for music nerds. After a quick break, we'll be back with Mr. Romantic himself, John C. Riley, to discuss how he sees the legacy of this great American songbook. Support for this show comes from Odu. Running a business is hard enough, so why make it harder with a dozen different apps that don't talk to each other? Introducing O-DU. It's the only business software you'll ever need. It's an all-in-one fully integrated platform that makes your work easier.

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That's O-D-O-O-O-O-O-com. John, thank you for being with me on Switch. POP. Yeah, my pleasure. So I want to start and just ask, who is Mr. Romantic? Mr. Romantic is a character that I created to perform love songs. And he is someone who, he's been alive for thousands of years. He's almost like a mythical character. He travels the world in a steamer trunk carried by four musicians.

When he comes out of the trunk, he has to put on a show. He doesn't have to go back into the trunk if he can find one person who will love. him forever. He hasn't done it yet. So the show, the show is continuing, but yeah. It was like this kind of improvised show that I came up with based on a bunch of songs that I wanted to sing, and it was inspired by Mr. Sellefane in Chicago, the movie musical that I made. And also And also I grew up doing And also I grew up doing musicals as a kid

And I always loved that kind of very performative style of singing And I also thought the world could use some love right now So I made a show about empathy and love and trying to fall in love. It's very sweet. There's, I mean, there's no cynicism. While there is a little bit of humor, it's mostly the album, just like pure love songs, heartbreak songs as well. Right.

Well, the album is different than the show. So I just described who the character was. But if you want, I can get into why the album sounds like the album does. Tell us about it, yeah. Yeah. So when we do the show, like I just described, I come out of this steamer trunk and I do all this audience work. I go into the audience and meet people, try to fall in love with them, and I fail over and over again, and we sing all these beautiful songs. And I dance, and I do pantomimes during

the solos of the songs, like, you know, mime kind of routines, like coming in a door, seeing a bottle of champagne, opening it, pouring some, giving someone a glass, like these little kind of like scenes that I do during the solos. And so when it came time to make an album of the music that we do for the show, I was like, well, the show is so visual. There's all this dancing and there's all this audience interaction. And I don't want to make like a live record because you won't even get what I'm doing. You'll just hear the audience laughing and stuff or whatever. So I thought like, what can I do to make the album more visual?

And so what we decided to do was intercut within the songs cinematic sounds. Yeah. So that while you're listening to the songs, you're seeing. kind of what the song is about, but we're creating these images in your mind through sound effects. Like Moonlight Serenade, you're meant to feel like you're literally standing at the gate at night outside of a house trying to get someone's attention in the house that you love, you know? So what do you hear, crickets? You hear like a whippoorwill in the distance. You hear a little bit of breeze in the trees.

And so what we tried to do is really put people into the place where we felt like the songs existed. And I stand at your gate. And the song that I sing is of moonlight. And thereby made a visual presentation of the show in an audio format, but the visuals are inside of your mind. So I hope it works. Oh, it's immensely world building. Like, dreams begins with a sort of waterfront scene. Jonesburg, Illinois, starts with a...

collect call from a prison. Hello. The following is a message you have received from inmate 3407 at the Johnsburg Correctional Facility. There's like a nightclub ambience and falling in love again. There's all of these wonderful

world building. Another reason I did it that way is because I thought, well, we can just record the songs purely. I have these brilliant musicians that I work with. We could just put out an album of the songs. But I thought Yeah, but that's just going to be kind of like

John C. Riley does your favorite songs from the American Songbook. And this show is designed like a play almost. It's a story that unfolds over and over every night. So, yeah, I just felt obligated to give the audience something more in the record than just the songs.

Okay, this is making a lot of sense to me because I'm thinking about your performance of what I'll do. Gone is the romance that was so divine, tis broken and cannot be mended. The Irving Berlin songs, about a hundred-year-old recording, and it has this sort of opening

verse that is often neglect. Gone is the romance that was so divine, tis broken and cannot be mended. Yeah, and a lot of these old standards have those that used to call it the verse, even though it's really a prologue for some reason the term that they used for it was the verse which was like I mean I personally there's a lot of different theories of why they would add these things

because sometimes the songwriters themselves didn't even write them like they were added later or something that the songwriter put on there that most people just ignore they get right into the song but I think one of the reasons they were doing it is like if you're singing you know what do and it's like a super popular

Irving Berlin song. Yeah. You kind of want to trick the audience at first so they don't know what song you're about to sing. You know, so it's almost like a little fake out. You know, and then when the verse, oh, there is the hit.

There's the song I know. What will I do? You know, like... You introduce it in a way where it feels like it's coming out of an old gramophone. So it's almost like these verses that were there that often get neglected are part of the world building that you were wanting to do on the record anyway.

Yeah, it's part of the storytelling of the songs, too. Gone is the romance that was so divine. You know, and that's another reason they add these kind of prologues at the beginning of the songs, I think, is also to set the stage. Like, I'm not going to just get right into the song. I'm going to, like, set the stage for you a little bit here. Like, for instance, on what will I do? Gone is the romance that was so divine, tis broken and cannot be mended.

You must go your way and I must go mine. but now that our love song is ended, what will I do when you are far away? So it's like it gives you context, which is also what I was trying to do with the sound effects, you know, I was trying to give people the context. Because I don't, you know, like, whatever, I'm an okay singer, you know, I'm not Frank Sinatra, I'm not Knacking Cold,

but I'm an actor who loves storytelling. So the way I sing a song is like, I really try to illustrate the story. for you, take you through what it is that we're talking about in the song, as opposed to just singing it beautifully for you in a musical performance. Like, I try to do it like a theatrical performance or an acting performance with each song, you know? Because they all have these really compelling stories to them, you know?

It's fitting. I mean, when we think about the Great American Songbook, these are a group of songs that were interpreted by so many different people. And so the appropriate interpretation by John C. Riley is through the character, Mr. Romantic, that has this extra world building. It has a theatrical component to it that feels very fitting. Yeah. I want to know more about your love of this music because Mr. Romantic could have chosen a lot of different songs to sing. And the majority, and I want to get into some of the more contemporary stuff later, but the vast majority of these songs are old Great American songbook recordings.

Yeah. Why these songs? I was looking for songs that had a timeless quality to them that seemed eternal. Like the kind of songs, you hear them the first time, and you're like, well, I'm never going to forget that song. You know, like, I've always been fascinated with this idea, like, what songs survive? What songs make it into the American song book? And why? Why are we still singing Amazing Grace?

What is it that gives a song legs? You know, what is it that gets a song passed along? And I think it just has this eternal quality. Like, it's not only the words, but it's the arrangement of the notes has an almost alchemical effect on a listener. You know, like the way the notes play out, there's something just, I don't know, it's hard to really put your finger on. But when a song appeals to you, you know, and a song lodges itself into your mind or your heart, it's there forever you know like what will i do is with me forever you know but i'm also trying to expand what the quote american songbook is it can't just be all songs from 1930 to 19 whatever 1920

from 1950 like america still exists the songbook is still being written to me someone like tom waist is in the same genealogy as irving berlin like he's an american and so to me tom waite's in the American songbook, but that issue hasn't been printed yet or something. I mean, I have to say, I had known you obviously as a musical performer through Dewey Cox or through Chicago, but I hadn't known about this side of you that was also just a musical performer. That's a really different medium. How did that come into your life? Well, I grew up doing musicals from the time I was eight years old, where I grew up on the south side of Chicago, like no one was doing straight plays, no one was doing Shakespeare. It was all, Hello Dolly, and the King and I, and

fiddler on the roof. So it was always a part of my life and music was always a part of my life. You know, I learned to play the guitar when I was like 18 or something, but there was a player piano in my house. My mother loved all these old standards, you know, Winchester Cathedral in the Days of Wiening Roses and all these great piano roles. So I had like a weirdly complete exposure to a lot of these kind of songs from a young age, not from recordings, from piano roles. I'm talking like player pianos. Yeah, player piano roles. Yeah, so I would sit there and sing them with my mom.

So I knew these songs from singing them, you know. So, yeah, music has always been a part of my life in a weird way. Like, I learned how to act at the same time as I learned how to sing. And so when I would do a musical, I learned how to sing through storytelling. You know, in the way that I just described, the way that my approach to singing was, through the musical theater, you know? So that's, to me, singing is storytelling.

Okay, this is coming together for me. Like, that musical theater was foundational. These are the songs, the Great American song but comes largely through musical theater. Yeah. And also, it serves such a different kind of musical and social purpose in its time that songs that came from theater

could be interpreted by anybody. Yeah. More and more, songs are, who am I dating, deeply person? It's hard to reinterpret someone else's song when it's about their specific. Right, the singer-songwriter era. You know, and that's one of the things that I feel like I'm not a part of the singer-songwriter canon, you know.

I'm a part of interpreters, you know, like Frank Sinatra, like Nat King Cole. Like, you know, like these guys took songs, even Elvis Presley, you know, he took a song that he thought was really great and he's like, you know, like, are you lonesome tonight? Is a song from the 1800s? Are you lonely from tonight? But Elvis was like this tonight Are you sorry

We drifted apart But Elvis was like That's a good song I'm going to sing that one You know like And then he makes it this He makes it his own Are you lonesome

Tonight Do you miss me tonight Are you sorry We drifted upon So that was kind of part of the mission, too, of wanting to sing these songs. Not only these American songwik songs, but before that, bluegrass songs, folk songs, blues songs, had a blues band before the folk band. So it was like my way of saying, like, this is a beautiful song, like, I'm going to do my part

in my time of passing it along to another generation. And some kid only knows me from stepbrothers might learn about a great bluegrass song because I sang it. Not because I'm the greatest singer ever, but people knew who I was, and I passed this song along to them. I think that's really an important part of music, and I think interpretation has kind of gotten a bad rap

by the singer-songwriters of our day. We love them. We're grateful for our singer-songwriters, but yes, it has changed the nature of the song. Now it's like somewhat about, you know, oh, you do covers? You know, like it's like not quite as cool as writing a song, but to me,

when I think about writing a song, I think like, and I did write one song with David on this album, but when I think about writing a song, I always think like, well, yeah, I could tell some story from my life or something, but there are millions of great songs out there already. Like,

what will I do already exists? So when people come to the shows, like, even when they came to my folk shows, I would say like, you know, I'm not here to sell you my new album. I'm here to share music with you that is already yours. It's like being on a beach and picking up a seashell. It's like they're everybody's seashells, but I'm just picking one up and saying, isn't this one beautiful?

You know, it's your seashell already. I don't own it. I'm just interpreting it and I'm keeping it alive by passing it along. And maybe what will I do? It has a chance of becoming Amazing Grace, you know, like a song that just repeated. over and over because someone cared enough about it and loved it enough to want to interpret it themselves

and offer it to their generation, you know? So I don't think I'm as good a singer as Frank Sinatra by any means. Or Harry Nilsson. Harry Nilsson passed a lot of these songs onto me. After he made the Lime and the Coconut song, they were getting ready to make another album and his producer was like,

okay, you got some more hits in you, just like the Coconut song, so let's do some of those. He said, I don't want to do that. I want to do covers of American songbook songs, or more specifically, songs from movies that really moved me as a kid, somewhere over the rainbow. Somewhere. You must remember this, you know, as time goes by.

So he made this record called A Little Touch of Shmilsen in the Night. That was a foundational record to me. And he made this record with an orchestra, and the great Gordon Jenkins did the arranger. you know, like, and as a result, he passed all these songs along. I learned, What Will I Do from Harry Nilsson? What will I do? That's a big part of the overall mission of this album for me is sharing things that I love with people

in the hopes that they might come to love them too. It's such a important reframing about the social nature of music. We're grateful for our virtuosos. Thank goodness we have these great divas that can wow and inspire. us, but music is also something that we all play together. And maybe if we don't play an instrument, we join in the harmony, or maybe we dance along. And I think one of the things that this record does is beyond just the world building that you establish. When we get into the songs, the songs are really in a place. I'm curious about the construction of the sound of this record. You have spectacular

musicians with you. And I feel, I have no idea how you made it, but I feel like I'm in a room with you and your whole band. That's exactly how I made it. We recorded this at a place called Nest Studios in East L.A. The recordings of, like, Louis Armstrong, some of the artists from the 1920s, like the sound that they created because of the, it was really the limitations of the technology.

They couldn't track anything because they were just all in a room together. Yeah, no multitracking. So I was like, that's what I want to do. I want to do what Louis Armstrong did. I want to do what Sinatra did. What microphone was Sinatra using? This one, a big old-fashioned ribbon mic, has all this warmth and presence, you know?

Okay, how do you do it in the room? Like, I'm not saying I'm Louis Armstrong, but there's something really, in our age of digital sound and cleanliness in audio and the obsession with removing mistakes and impurities, we've lost something or the holisticness of music. And I think that that was really, important to me and David, my co-producer on the record, my right-hand man, you know,

David Garza. So I knew that, you know, something sounded a little crunchy here or I went slightly flat here or something like that's just the way it was going to be. I've always performed on stage without in-ear things. I rarely even use monitors. I like to just do the mix in my own head because I think, I don't know, I watch, sometimes I watch bands perform live and people, you can tell they have in ears on. They can't hear anything of what the audience is doing. They really can't even hear each other on stage. They can only hear what the sound man is putting into their ears. And then it separates you. It does separate you from the moment. Yeah, I think, I mean, it just wouldn't be appropriate to how you're trying to communicate this music. If this were

perfected by comping together multiple vocals, it wouldn't work. There were moments where you can hear the little screech of the bow on the violin and very quietly. And sometimes there's There's just like these little moments of something just slightly out but feels very right at that moment. Yeah. And there's something like David Byrne once said, audiences don't trust a singer that's perfect. I use my flaws to my advantage. In other words, the little mistakes or the little idiosyncratic things about his voice make him seem more real to us, more relatable to us. So like hearing those little things, those little squeaks on the violin or like or even like a little cliquette.

clunk against the upright bass of someone's hands touching it. It makes you realize, like, these are human beings making music. And I think the temptation with all of our tools that we have now is to clean things up so much that it's no longer human. It's a machine. It's a computer or something. It's more perfect than human beings are. Human beings always make a little, there's always imperfections or gray areas in what we do.

That's just who we are. So our approach to the recording was very much that. And believe me, there were moments when I was like, damn, and I wish I just isolated myself in a booth. We could have done this or that or this or that. But David told me over and over, he's like, John, you don't understand, you have to stick to your guns on this because most people don't even understand what they've lost

by giving up by what you're embracing in the way we're doing this. Oh, I mean, it comes off so clearly. I really have that experience of like, oh my gosh. I almost feel like I need to be quiet while listening to the record because I can hear all these nuances. It's also a throwback in a way because we're also like the record is presented in one stream. Obviously, you need to flip the record if it's vinyl,

but it's meant to be listened to for 44 minutes straight, strung together. Like Harry Nilsson's record, a little touch of Schmielsen on the night, it has these orchestral transitional things. Like there are no pauses between the songs. It's like a dream almost. It's almost like a childhood dream of Harry Nilsons

as he's watching movies or something as a kid. Anyway, I'm a big believer in human beings and all of our flaws and idiosyncrasies, you know? And the craft of making music should feel human. It shouldn't feel like a machine to me. Does it feel like it comes to longerheads with it in some ways the mission of this record, the idea of wanting to be loved for just who you are?

Yeah. You can't do that without imperfections. Right. And also, the record and the whole project in itself is, I think, like a stand against the robots. You know what I mean? It's like saying, like, human beings matter. Love matters. Connection matters.

Storytelling matters. Imperfections are okay. You know, like there's something, I don't know, there's something really self-loving and human about. that. Okay, and so one of the things in this larger human project that we alluded to earlier was bringing in some more contemporary music. And I want to spend some time talking about the Tom Waits interpretations and your original recording as well. You've brought three Tom Waits recordings in here, the opening. Right. Yeah. Just another sucker on the vine. The band comes in. I don't know. There's just something time. Again, timeless and eternal about Tom Waits' approach to things and what's a lot. important. And talk about embracing mistakes or embracing imperfections. Most gravelly voice on the planet. Yeah, but not just his voice, but his percussion. And, you know, like, he plays the piano like, he plays the piano like he plays the drums,

you know, like he plays only the black keys, I think. Most of the songs are just the black keys, which is so interesting. Like, anyway, so Tom Waits, we chose Tom Waits because, I mean, it's a very high bar who made it into the songs that I chose for Mr. Romance. and it is an eternal quality, and it is a song that seems like it's been here forever, you know. And to me, Johnsburg, Illinois, is one of the most beautiful songs about love I've ever heard. She's my only true love. She's all that I think of. Look here in my wallet.

That's her. It's also one of the shortest. But it packs such a punch. It's so, like, sincere. And it's a song about worshipping someone that you love, you know, and admitting to yourself that you love them. And same with The Picture in the Frame, the other song that we do by Tom Waits, you know.

The sun comes up, it was blue and... Ever since I put your picture in a frame. The sun comes up, it was blue and gold. ever since I put your picture in a frame. You know, like, it's the transformation that occurs to you once you've fallen in love with someone. You know, Tom has this ability to capture the true moments of our lives. You know, these phrases and sayings that he used, these truisms, you know, always give

a diamond in your mind, you know, like, and this idea is that, you know, like, ever since I put your picture in a frame, it's like, that is so concise, you know, and, it's, And it really resonated with me because I remember when I put my wife's picture in a frame, it was this moment of reverence. Like, you know, this person means so much to me. I'm not just going to keep this photograph. I'm going to put it in a frame. Anyway, yeah.

So, Tom, to me, is someone that is very much as much in the pantheon of great songwriters as Irving Berlin or as Louis Armstrong, or as, you know, some of the other great songwriters. I mean, frankly, I shouldn't say you fooled me, but I was. I was really curious. I remember when picture in a frame came on and I have listened to mule variations, which I think is 1999,

dozens of times. And I heard this song, I heard you singing it. And I was like, what is this? I've heard this. It must be like an old blues from the 20s. There you go.

I mean, it is a blues structure. There's like 10 lines in the whole song. And I was like, oh, it's that simple. It's got to be a real old one. It's very,

and it's very good way. And it's also another one of those turns of phrase. Like, waste is just a, genius. Apparently I heard that he has, I've met him a couple times. I'm just, I literally call him St. Tom because he's so important to me. So yeah, it's my tribute to Tom in a way of putting him in the same place as Louis Armstrong and in the same place as Irving Berlin. In a way, this is someone who is one of the all-time greats, you know? Let's maybe close out then on an original song.

what guides the lost ship to shore. Oh, yeah. So it's an original song, but it's also not an original song. Wait, what? Help me out. Yeah, so we close every show with a song called Ragtime.

It's an instrumental song by Randy Newman. It's from the original soundtrack that he wrote for Ragtime. And I just love it to, dun dun da-dun, dun. There's just something, Randy, Newman is another one. He is just in the pantheon of greats. Like he he is tapped into a timelessness and an eternal quality in his music that's very few people have. You know, and he comes from a lineage of great songwriters and composers. So we always use this song as our exit music, right?

At the end of every show, it's what we exit on. And I say goodbye to the audience during that song. And then we were kind of like, we got to the end of the album, like, well, we can't see us exiting. we need like a mission statement at the end of the record here and so Davids like well why don't we just write words to ragtime and I was like that's a lot of nerve David we can't just take a Randy Newman song and add words to it and then Davids like well why don't we ask permission and so we had someone ask Randy Newman and he was like yeah sure

but you got to call it something else because my song's called ragtime if you make words to it you got to call it something else So we call it What's Not to Love, which was already the title of the album from the beginning. And kisses from heaven above. Oh, darling, what's not to love? And it's a question. It's almost like a challenge to the audience. What's not to love, you know?

What do you want to leave people with with what's not to love? I want to leave them with an appreciation for human beings and all of our frailties and all of our beauty. And I want to leave them with some songs that I loved, and I hope that they love them too. You know, especially younger people who only might know me from movies or something. I want them to have the experience I had

with Harry Nilsson's record, a little touch of Schmielsen in the night, which is also available, by the way. But this is my attempt at, like, passing along, some beauty and some joy and some love. I really appreciate it. Thank you so much for joining me. Yeah, my pleasure.

Thank you, John. Nate, I have a question for you. What has two thumbs and loves the Great American Songbook? This guy! I'm sorry, what was your question? Well, clearly, you love this repertoire. Yes. When you sit down at the piano, what do your fingers just naturally play from the Great American Songbook?

What a fun question, Chuck. Probably another Gershwin tune, like, they're writing songs of love, but not for me. A lucky stars above, but not for me. Anyway, why do you ask? I don't know, just wondering what you love. I mean, I just, we get to spend so little time together. We spend so much time together, but so rarely in person. When we went on our book tour back in 2019, we were in Seattle.

Uh-huh. And the hotel had a grand piano in it. Oh, yeah, yeah, yeah. And you went over, and I think you were really into neck and Cole at that moment. Yes. And I remain. But I was particularly taken with songs like, I don't want French fried potatoes, red ripe tomatoes.

I'm never satisfied. I want the Frim Fram sauce with the Austin Faye with Shifafa on the side. Oh, Frim Fram sauce. That Fram got a fun night. Our friend Rich Smith was there of The Stranger. Yeah. That Frim Fram got everybody moving in that hotel.

You mean all three of us? Yeah. There were at least seven, I think. I think by the end of the night, there were just a few, but it was, yeah, that was a blast. And it got saucier throughout the night. It just goes to show these songs on the piano, they create such a good time. It's something I want more of in pop music. That small group, communal get together to sing their favorite songs.

I really love exploring the Great American Songbook with you, bud. Switched on Pop is produced by Rana Cruz, edited by Alyssa Soap, engineer by Bradman-Farlane, illustrations by Iris Gottlieb. Our theme music is by Jossi Adams and Zach Tenario of Arc Iris. We're a member of the Vox Media Podcast Network and a production of Vulture, which is also part of New York Mag. You can subscribe to New Yorkmag at my mag.com slash pod. Tell us your favorite songs from the Great American Songbook,

or, you know, your favorite covers of these songs, because you don't have to go far to find them. And you can tell us about them on social media at SwitchDon Pop everywhere. At Switchon Pop. Or on our substack where there's also a chat. You can chat with all the other people that love talking about this music.

It's also called Switched on Pop. We'll be back again next week on Tuesday. And until then, thanks for listening. Attention, Spotify. Has arrived on Google Jasmine Absolute of Carolina Herrera, a fragrance intense with character Gourman and addicivio. Imagine a jasmine-envolventy, caramelized and tonka-tosted.

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