Switched on Pop - Frankly, Sinatra still matters (with Seth MacFarlane)

Episode Date: June 10, 2025

What if the Chairman of the Board's biggest contribution to music wasn't his voice, but the blueprint he created for modern pop stardom? Frank Sinatra didn't just sing songs: he invented the concept album, injected his full personality into every performance, and created a template for artistic control that today's biggest stars still follow. His influence runs deeper than you think: Amy Winehouse titled her debut Frank as tribute, Jay-Z calls himself "the new Sinatra," and Frank Ocean borrowed his name from both Sinatra and Ocean's Eleven. That influence extends to unexpected places too: Seth MacFarlane, the creator of Family Guy, has been championing Sinatra's orchestral style for years, and through his friendship with the Sinatra family gained access to over 1,200 boxes of never-recorded arrangements. His new album Lush Life: The Lost Sinatra Arrangements features songs that arranged for Sinatra but never performed, uncovering musical treasures that reveal new insights into how the Chairman of the Board's innovations still shape the sound of pop music today. More Subscribe to our newsletter to receive your own bingo card! Songs Discussed Frank Sinatra "Fly Me to the Moon" Frank Sinatra "All the Way" Frank Sinatra "In the Wee Small Hours of the Morning" Frank Sinatra "Something" (Beatles cover) Amy Winehouse "Halftime" Jay-Z "Empire State Mind" Frank Sinatra "Strangers in the Night" Frank Sinatra & Nancy Sinatra "Something Stupid" Frank Sinatra "New York, New York" Frank Sinatra "My Way" Sonny and Cher "I Got You Babe" Frank Sinatra "Laura" Seth MacFarlane "How Did She Look" Seth MacFarlane "Lush Life" Seth MacFarlane "Give Me the Simple Life" Seth MacFarlane "Shadows" Seth MacFarlane "Who's in Your Arms Tonight" Learn more about your ad choices. Visit podcastchoices.com/adchoices

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It's free for iOS users. Welcome to SwitchDon Pop. I'm musicologist Nate Sloan. And I'm songwriter Charlie Harding. Charlie Frank Sinatra, he is a larger than life figure in popular culture, right? I can picture him right now, you know, with his suit on, the fedora, the big U-47 microphone in front of him. He is the chairman of the board, one of the best-selling artists of all time. He invented Vegas culture with the Rat Pack.

He's an Academy Award winner for acting. He's a style icon, as you said. He had relationships with the most glamorous women in Hollywood. He had connections to the mob. His mugshot is a poster, literally, that you would see in every college dorm room. And his voice has been endlessly imitated to the point that Sinatra is basically its own genre. I did it. way.

So he's like an octopal threat. Yes. And this mythos, I think, almost obscures the talent and the innovation that was at the heart of his persona. And 27 years after his death, his sound still shapes the way we make and hear pop music. And people are still discovering new things, new recordings, new insights about this. iconic singer, like, of all people, Seth McFarlane is celebrating Frank Sinatra's legacy with a new release called Lush Life, The Lost Sinatra Arrangements. So you're saying you can connect Seth McFarland of Family Guy Fame and many other shows to the history of Sinatra directly. But you're also

claiming pop music still owes something to this guy? Well, we'll talk to Seth about that a little later, but right now, Charlie, I want to understand why Frank Sinatra is so important to our musical culture by focusing on five things he did to change the sound of pop. All right. So we're going back in time to like post-war era. We're going to cover the 50s to the 90s, Chuck. I mean, we're talking about one of the key figures in the 20th century, not just any particular decade. And I feel like we have to start with the voice itself.

The beautiful baritone. And out of the thousands of songs Frank Sinatra recorded, let's start with one that I think people really identify with him. Fly me to the moon. Fly me to the moon. Let me play among the stars. Let me see what spring is like on Jupiter and Mars. In other words, hold my hand. A song I used to teach the importance of the right title, the song was originally going to be called, in other words, imagine the world in which we never have Fly Me to the Moon, a phrase that he only sings at the very top of the song. Okay, well, yet another lesson that we're learning from Frank, but I want to talk about how does he convey this song

in a way that is so indelible. And we have to start with rhythm, right? I think that's one of the key elements of Sinatra's delivery. Every note is right where it's meant to be. Fill my heart with song and let me sing forever more. We might call this phrasing, when you hear Frank Sinatra sing, you know it's him because no pitch is out of place. There's the almost metronomic like quality where he's just completely glued in with the drummer at the beginning. And then he has these beautiful longer melisma's to give you a break from that really tight rhythm. I think this is why his interpretation, of classic songs have often become the definitive version because he delivers them in a way

that just sounds so perfect and right and true. Then there's the intonation. Like, this guy does not sing flat or sharp. He is so perfectly on key. It is uncanny. Even when he has to reach or go down low, it's so comfortable. It's like he's got autotune 30 years before that software was ever invented. So there's rhythm, there's intonation, and then there's one other thing that is so recognizable. It's the way he sings his vowels. And Charlie, I don't want to explain this to you. I want to have an expert on Sinatra talk about it.

How about Michael Bublae? Sinatra would sing hard on his vowels. All the ease, oh, ooze, he would, you make me feel so young. He really would eat. I used to be hanged with it. He really did. If you heard him, it was, you know, you. All these wonderful things.

What a great impersonation. That's spot on. That's from a CBS interview Boubley did with Dan Rather. And these three things, his approach to singing vowels, his perfect intonation, and his flawless sense of rhythm, I think, are what makes his vocal style so effective. Okay. Let's go to the next innovation, Chuck. Okay.

Frank Sinatra created the concept album, as we know it. What? I know what you're thinking. It's The Beatles or someone. It's Sergeant Pepper's Lonely Hearts Club band. Maybe there are other contenders as well. I would think Dark Side of the Moon. There you go. Pink Floyd. No, Charlie, it's 195s. What? In the wee small hours of the morning. It's almost like an inverse lullaby where you have toy piano or something in the background, maybe just vibes. Shalesta, I think, is what we're here. Oh, yeah.

So that gives you that sort of like lullaby quality, but we're waking up. And I feel like the chromaticism in the arrangement of the strings feels like the sun slowly rising, the light coming into the day. It's very visual in the way that it's presented. The concept of this album was essentially. loneliness, I would say. This is an album just full of sad songs. And it might not seem that radical, but prior to this, an album was just a collection of unrelated singles. Sinatra was the first to think, no, no, we can use this new technology, this long playing record technology, where we have 20 minutes aside, maybe 40 minutes total, to actually tell some kind of story,

to have some cohesion. And he did this in a number of ways. And he did this in a number of ways. Like, later, he would do these collaborations with different artists. He released albums with jazz icons like Count Basie and Duke Ellington. He did albums with Quincy Jones. And he even did an album with the Brazilian Bossa Nova legend Antonio Carlos Jobim, which showcased Sinatra's ability to step outside his kind of home base of jazz and standard pop. So in some ways, we owe not just the idea of the concept album, but it's almost like the album as a whole because albums today are meant to have a larger identity,

even if they don't have a unified concept. Wow, had no idea. Very closely related to this is his third innovation. He injected his personality into everything he does. If he's a larger than life figure, it's at least in part because he did not shy away from showcasing his humor, his celebrity, sometimes even his anger in his performance. You can hear this, especially in the live performances he recorded. I want to listen to a kind of obscure one. This is 1959 Sinatra Live in Australia with the Red Norvo Quintet.

This was unreleased for a long time, was only available on bootleg, and check out what he does in a performance of the standard all the way. It's no good unless he loves you. Nobody sleeps in this act, Freddie. Okay, what just happened there? What did you say about his auto-tune, like, capacity for pitch? I said he never missed a note, but clearly he did there. What's happening? My reading of this recording is that someone, either in the audience,

or maybe even one of the musicians on stage, is sort of distracted or maybe even nodding off. And Sinatra doesn't miss a beat. He sings the chorus of this completely off-key. And then he says, hey, there's no sleeping on the job on this. one. This is such a small moment, but I really feel like it captures what was so magnetic about Sinatra. Like he was himself and he would mess with you and that comes through in so many of his recordings. He sounds so relaxed, so himself. Okay, fourth innovation, Chuck. Wait a minute.

You keep saying Sinatra innovations. Shouldn't there be a word like Sinatravation, synivation, Frankisms. I like Sinatravations. Let's go with that. Sinatravation number four. Frank connected the world of jazz and standards to the world of pop music. And I don't think this gets enough credit. He bridged a generation gap.

Towards the end of his career, he started to sing not only the music of the 30s, 40s, and 50s, but the music of rock and roll, the music of the Beatles, of Billy Joel, of Linda Ronstad. Check out Frank's interpretation of the Beatles' Something. Something in the way that she woos me. Don't want to leave her now. Better believe than how. He made it swing and he made it more lush than the original. If rock has become a part of the modern canon, I feel like Frank Sinatra has to take

some credit for that because he took these songs that were sort of at the margin of what was considered like the canon of pop music and he brought them into the fold he let these songs coexist alongside the likes of rogers and hammerstein and irving berlin and the gershwin brothers it's like he's gone from the great american songbook to like the new great american songbook and on his final two albums simply called duets one and two he really reaches across the aisle in terms of the people that he's duetting with you find luther van dross on there she never bothers on it with people she hands and that's why the lady is a champ

Aretha Franklin What now my love That you're going to feel St. Frank sang Frank in Gladness For once in my life I've got someone who needs me Kenny G

Or it soon might explode I mean, the variety of people he duets with is truly remarkable. And it's a testament to how big his ears were, just how open he was to new sounds and new collaborations. All right, Charlie, I've got one more sonatravation for you. Number five. And this is less about Frank himself than about his legacy. Because I think he's largely seen as part of another era. But I think if we listen to some of the most important vocalists of the 21st century,

we would find that they all listen to Frank Sinatra. Case in point, Charlie, to me, one of the most significant figures in 21st century music is the late great Amy Winehouse. Yeah. And she was a true Sinatra devote. She titled her first album, Frank. Did you ever think about why that was, Charlie? It wasn't just because she was, you know, candid and honest.

And Frank, it was a tribute to Sinatra. And we can hear this really clearly on an unreleased song. from those sessions called Half Time. And when Frank Sinatra so I sing the standard sheet. It's too much to take. So think of every singer now who's been influenced by Amy Winehouse. And then think of Frank Sinatra kind of in the shadows of that sound.

Yeah. And this isn't even to mention his influence on hip-hop. I mean, he is such a central figure. central figure. There's like Tony Montana and then Frank Sinatra, I would say. You know, Jay-Z dubs himself the new Sinatra on Empire State of Mind. The rapper Logic calls himself Young Sinatra and a little artist by the name of Frank Ocean. Are you familiar with him? He gets his name from our friend Frank Sinatra and the title of the classic Crime Caper Ocean's 11, which Sinatra started in the original version. And I'm sure that.

there are many other references that our listeners can fill us in on. Yeah, I want to see all the Frank heads peek out from under the fedoras. The Bobby Soxers. The what? Those were his fans in the 50s. Really? Yeah, they were like young women who were liberated, financially independent. The Bobby Soxas.

Maybe we need a second coming of the Bobby Soxers. All right, Charlie, there's five Sinatravations that make Frank one of the most important figures, not only of the 20th century, but of the 21st. And like I said, I feel like we're still learning more and more about this artist and sometimes from some seemingly unlikely sources. Yeah, I actually got to sit down with Seth McFarlane, whose new album, Lush Life, uncovers some of the hidden gems in the Sinatra archives, arrangements that were never put together by all of his best arrangers. And it turns out, you know, Seth MacFarlane has been singing in this great mid-20th century style for quite a while now.

He is an amazing vocalist, similar range as Sinatra, and is revitalizing these tracks on his album, Lush Life. And I think Seth MacFarlane might reveal some further sonatravations right after the break. Maria, you have a podcast now and you need to start acting like it. What's the first step as a podcaster? Well, you have to ask lots of questions. I'm Maria Sharpova, and I'm hosting a new podcast called Pretty Tough. Every week, I'm sitting down with trailblazing women at the top of their game to discuss ambition, work ethic, and the ups and downs that come on the path to achieving greatness. I have a few pretty tough questions for you.

Okay. Ready? Ready. Do not sugarcoat something for me. No. No. We'll dive into their stories and get valuable insights from top executives, actors, entrepreneurs, and other individuals who have inspired me so much in my own journey. Pretty tough is your front row seat to the women who have done.

demonstrated the power in being unapologetic in their pursuits. I hope you'll join us. New episodes drop Wednesdays on YouTube or in your favorite podcast app. Frank Sinatra's influence continues to reveal itself in unexpected places. Seth McFarlane, yes, the creator of Family Guy, has been recording and championing orchestrated music in the style of Sinatra for years, but his latest project goes deeper than tribute. Through his friendship with Frank Sinatra Jr., who appeared on Family Guy multiple times,

Seth developed a relationship with the Sinatra family, and when Frank Jr. passed away, his sister Tina Sinatra approached Seth with an extraordinary opportunity, access to over 1,200 boxes of Frank's musical arrangements, many of them never recorded. So Seth worked with Sinatra archivist Charlie Pignon to find buried treasures amongst these boxes, finding arrangements from Nelson Riddle, Billy May, and Dan Costa that Sinatra never got to share. I'll forget you, I will, while yet you are still burning inside my brain. The result is lush life, the lost Sinatra arrangements, an album that doesn't just honor Frank's legacy, but actually extends it. I sat down with Seth to talk about unearthing these musical artifacts and what it's like to step into Sinatra's shoes. Congrats on this release. It's very exciting.

I'm curious, you know, you've been channeling Sinatra, I feel like, for so much of your career. Could you just walk me through the development of your relationship to Frank Sinatra, from your own personal relationship to the music to building relationship with Frank Jr., the family, getting to where we are today? My way into Sinatra's music was sort of a backdoor way. I was a big fan of orchestras. I was a big fan of film music. I loved John Williams. I loved Horner. or I love Goldsmith. I was just really drawn to the fact that that music was both complex and easily accessible.

Like I wasn't listening to Bach. I wasn't listening to John Cage or... John Cage, right. That's extreme. But, you know, I was listening to what it was ostensibly classical music, but for somebody who didn't yet have the capacity to really appreciate classical music, it was accessible. and yet still seemingly high art. And I listened to so many of those scores today, and I was like, well, they still sound like high art to me.

And so I kind of found my way into his music that way. And then when I got to college, I bought a Sinatra CD at the store. I went home and played it, and I, for the first time, was hearing what was going on behind his voice. Come fly with me. Let's fly, let's fly away. I was hearing what I loved about the film scores that I love,

is that, oh, this is a form of classical arranging. This guy is singing to something that's really sophisticated. And so that was kind of how I found my way into his music, was through the orchestra. And setting the stage in the background, what are your friends listening to? Is this like peak nirvana era? This would have been peak nirvana era. Yeah. So, so Kirk Cobain, who's coming out of, yeah.

Doing his own things, singing a very different way. You're over here listening to Frank. Yeah, yeah. I mean, the thing about Sinatra is. is that there was always, and I think, I would assume nowadays, it's probably the same thing. There was always a place for him. Like, you would walk down to like the snack pit,

whatever the hell they called it, at RISD. And every once in a while, somebody would be playing Sinatra on the jukebox. Like, there was always kind of a space for Sinatra in the same way that there is now. He always kind of has his pocket of awareness. Like, people know who he is. They know his music.

They instantly recognize his voice. And then your connection to Frank Jr., through Family Guy. How did you eventually be, the family to the point where obviously you have a close relationship for the family are now working together collaboratively. Well, Frank, I think I had seen Frank Jr. on the Sopranos. Don't let him scare you. He's not really a nasty fuck. He's an incredibly nasty fuck. Hey, chairboy of the board. Read your fucking gods.

And as I recall and thought, hey, maybe he'll do our show. And sure enough he did. And we thought, well, maybe he'll sing. And sure enough he did. And I mean, it was a blast. It was, you have Frank Sinatra Jr. come in. You know, he sounds great. And you're singing those kinds of tunes. Frank Sinatra's restaurant. And you were singing as Brian the Dog and a sort of Sinatra-E-ish impersonation. It plays both capital and yes reprise. That's reprise.

At Frank Sinatra's Restaurant. Brian the Dog was my sort of way in to kind of do that stuff for a mass audience without really having a sing in a funny voice. But it was fun because he was also a real scholar of this music. and turn me on to some orchestras that I had never heard. I'd never heard of the Sauter Finnegan Orchestra. I said, what's that? This really experimental orchestra from the 50s and 60s

and that he introduced me to. And I went out, I bought some records and he was like, this is wild stuff. Like, this is like Esquivel, even freakier. I realize you've been kind of trying to Sinatra pill the world for a long time, all the way back to the theme song Family Guy. It seems today. that all you see

is violence and movies and sex on TV But where are those good old fashioned values On which we used to rely To, you've been releasing music on your own No one ever tells you What it's like to love and lose Yeah

So with full orchestrations I feel like yeah You've been sort of secretly Trying to get this into the world Yeah For a while Because you know he I feel like he represents

A real moment of generational change, right? Like, he's one of the biggest artists in the world just before the counterculture and sustains a career through the counterculture. Some of his greatest works, even like New York, New York. Start spreading the news. It's a very late song, and it's a huge song.

He had bursts like that during the point, you know, where he had like the sideburns and he had like the fringe jacket where you could see him like trying to kind of find his place in that world. Moments like that where there was releases like that Like 1980, I think? Yeah, where he would release something like

Strangers in the Night. Strangers in the Night Or, you know, something stupid with Nancy Sinatra. I know I stand in line until you think you have the time to spend an evening with me. Or even my way when we thought, you know, he's going to retire. That's a song that came out in the era of like acid rock. Yeah, yeah.

Apparently he didn't. I've always heard of. that he didn't like it. He didn't like my way. It's not my favorite Sinatra song, by any means. Yeah. The best example of that shift that I have seen, just because it's so blatant,

there's a video on YouTube, and the musical guest is the Rolling Stones, and Dean Martin is hosting. Huh. All the Rolling Stones, I've been rolled while I was throwing myself. I don't know what they're singing about, but here they are at.

And they do their song, and they come back to Dean Martin. He goes, Rolling Stones, aren't they great? Rolls Tom, having great. And he like rolls his eyes. Oh my gosh. And the audience laughs.

And it's like, and you can see it in this. It's like there's like there's like he doesn't quite get like what's what is this. Yeah. Which, you know, to some degree I can kind of put my head in his head and picture what that moment must have been like, yeah, that must have been like. Is this music? What is this? Yeah. But it probably a lot of it came from fear.

Yeah. This was like an expression of fear that like, what? What's happening? And it was so fast, too. It's like 1950, Sinatra is just the biggest thing in the world. And then suddenly, a decade later, it's just, it's all changing. So tell me about we're now, gosh, what, three quarters of a century after he enters the world and is, you know, the biggest artist in the world. What do you feel like he's offering, and your rendition of his work is offering in contemporary music?

It all goes back to what got me into that music in the first place was this is popular music. Yeah. that is orchestral. An orchestral in the real sense, not just we're going to put 30 violins on stage and they're all going to be playing the same fucking note. I always feel a little bit bad for... I do too.

You see a really great pop act. You admire and then they bring an orchestra up on stage and they're just playing something in unison. You know there. And from getting to know some of these guys, it's like, I think they hate it just as much as we think they do. It's just because they're like, I went to Juilliard, man.

Because it's like you're playing the same riff over and over. What's the magic of the orchestra? What sort of like emotional places Because of the diversity of sound you can get. I mean, that's the thing. It's like, you have an orchestra, you can do anything. And that's what I love about his music. And the music of that era, there are just so many different kinds of sounds you can get with one ensemble.

And that's the thing, I think for me that if I can inject a little bit of that back into the awareness of the industry, that it's certainly not going to hurt. Part of this is like, I have not developed an ear for contemporary music the way that probably I should before I start mouthing off like this. So I'm aware of that and that, you know, feel free to at me angrily. But it is something that's, that I think has been, has been kind of lost. You know, when we play this pop music, there's a French horn up there. There's a cello up there. There's a harp up there. There's a fucking oboe up there.

There's a string section. There's a clarinetist. There's flutes. The oboists don't get enough appreciation in the world. I think the one pop song I think of is, Sonny and Cher. I got you, babe. But it's always like a novelty.

Oh, no, no, yes, yes, yes. It's something that's so specific. It isn't something that's kind of just in the mix. And I think to me, that's what I don't really hear that anymore. I'm curious, why is now the right moment for Lush Life, the Lost Sinatra arrangements? I think really just because it kind of found us. Frank Jr. used to do Family Guy from time to time.

And when he passed away the stewardship of the library of Sanatrable, Natra arrangements went to his sister, Tina. And she came to me with the idea of essentially acquiring this library. I jumped at the chance. And it was about 1,200 boxes of arrangements that had been saved by Frank Jr. For many, many years. What we found were probably a little over 100 charts that he had never sung. These were buried treasures that gave us the idea to make an album.

And one of the things that he did that was so great, which I've tried to take a cute from is he would find songs that weren't necessarily well known, and he would make them well known. He would bring them back into the popular sphere. Can you think of a great example of one that he brought back? Fly Me to the Moon, which was a ballad prior to his recording of it. Yeah. It's the one that kind of turned it into this uptempo song, and that's obviously the arrangement that everyone knows so well.

Fly me to the moon. Let me play among the stars. I mean, that's probably the most obvious example. So I'm curious about how you went about uncovering this archive. So you've got thousand-ish works. I was just upstairs looking at some of these really beautiful arrangements. Yeah. What was the process of unearthing them, making these selections,

choosing these songs that I guess maybe it's safer to interpret Frank if he didn't do these songs, but he was going to? Yeah. I usually go out of my way not to sing songs that Frank has sung just because. you're never going to out Sinatra Sinatra. Right. But, you know, one of the parts of the process that was just something you kind of have to do, which is the fun part, is you hire an orchestra. Right.

Because you don't really know what you have in there until you record it or until you rather play it. So we hired an orchestra. We went over to 20th Century Fox at the Newman stage where we record family guy and American Dad. And just kind of went through the boxes and said, well, what about this one? Huh. What's this? This is an old yellow piece of music. that has the name Nelson Riddle on it, what's this?

And that was really how we found the songs that we ended up putting on the album. So you kind of are you're demoing them with the orchestra. Yeah, you're hearing things that were put to paper. And in many cases, in most cases, never played. What are you listening for in that demo session? And are you singing along with it? Yeah, I was, I was, yeah.

In that session, I was listening for songs that were kind of fully formed, arrangements that were fully formed, songs that seemed like they were entire entities in the way that all of the songs on Frank's records are. Was there a moment in that studio session where something like clicked, we're like, oh, that arrangement's going to work? Like, we've got to do that.

Yeah, yeah. There are songs that were instantly obvious in the same way that you listen to a Sinatra record that you haven't heard before and you kind of instantly recognize when something great is happening in the studio and when something great is happening on the page. I really love the arrangement for her, how did she look? So you ran into my former fiancé. Yeah, that seems to be everybody's favorite. Huh.

Yeah. What do you think stands out about it? Well, first of all, it's Nelson Riddle. Yeah. And Nelson Riddle around 1958, which is like peak everything. It was written as a candidate for Only the Lonely, which for many people, me included, was probably Sinatra's greatest ballad album. His voice was at its absolute peak.

Riddle was at his absolute peak as far as what he was writing. That whole album is just a work of art. And it has obviously the idea of a concept album, which Sinatra essentially invented. Right. I mean, We Small Hours, which is kind of, you know, still stands as the first record album that had kind of a fully formed concept. In the we small hours of the morning,

It's just all depressing in the best way. I mean, it's like, it's, it's what eventually became, you know, Alanis Morissette's discography. I mean, it's like, it's just, these are sad songs of loneliness and heartbreak and self-pity. So the arrangement of how did you look kind of has that same vibe. Yeah, well, that only the lonely, which was one of his, I think Only the Lonely was a few years later and only the lonely was the sad concept album brought to perfection.

It was kind of baked to perfection. Each place I go on. Like that was when the sophistication of it in both vocals and arrangements is just kind of unmatched. So how did she look was a candidate for that record. And there's not one chart on that record that isn't just a work of genius. Yeah. And you can hear it too.

I wish Sinatra had sung this song because it would have been kind of epic. The climax of the song towards the end. I'm literally getting chills on the moment thinking of it. Not that I really care. Yeah. The build. The incredible dissonance that you hear in the orchestra. Oh, yeah.

And so much of it is not in tempo. She asks about. That's the other thing that I think you, you know, how difficult that is. Like, you can't fake that. Tell me about assembling your final orchestra. You put it together at Skywalker Ranch and Marin. Skywaker Ranch, yeah. Yeah, there's a great soundstage up there.

And it was a combination of L.A. musicians and English musicians. And it was put together by a combination of Joel McNeely, who was a composer and conductor that I've worked with for many, many years. Just brilliant guy. and John Wilson, who's one of the great orchestral conductors in the world, he's worked with the London Philharmonic LSO for a long time. And he has an orchestra that he is assembled that he's worked with for years, called the John Wilson Orchestra. And what they do is they play MGM charts from the 1940s and 50s

that only exist on old mono recordings. Oh, fun. And he's reconstructed these things. And it's really something like, I went to London in about, I guess it was 2010, to sing with his orchestra. I heard their recordings, but I never heard them live. And I walked into that rehearsal space,

and they were playing, they were playing somewhere over the rainbow from The Wizard of Oz or singing in the rain. It was something, it was one of these iconic charts that we all know, but we're all so used to, you know, hearing like this. And it was like, you get chills. Yeah, this is an 80-piece orchestra

playing with the tightness and intensity of like a six-person jazz combo. Never heard anything like it. And that's what the contract orchestras obviously used to do at MGM. They were the same people playing together every single day so that every person knew

the rhythms of the person sitting to their right and to their left in front of them and in back of them. He assembled his kind of hot shots and Joel assembled ours. And what we have is this orchestra that was really, really up to the task of recording these things just as they would have been recorded in the 1950s. Because it is, you know, there are things that it's the charts, it's the way they're sung,

but it's also how they're played. I mean, there's like the vibrato that the strings add and the frequency of that vibrato and the vibrato of the trombones and the dynamics of the orchestra are, you can just change the whole feel of a recording, particularly with this kind of music, if that's done correctly or incorrectly. Tell me about the process of being in this group

and what it feels like. I mean, you've got a 70 piece orchestra, yeah. your conductor, and you've got you. And of course, in the recording, we're really paying attention to the voice. When we hear Frank, we're thinking about Frank, but there's so much support that's going on in that room.

What is the experience of being in that room like for you performing live with that group? It's yet another confirmation of what has been evident all along with Sinatra's music. And to some degree, I think Nat King Cole is the only other vocalist who I think really kind of got this. But it underscores what Sinatra really knew, what he understood about what

an orchestra could do for him. No question Sinatra as a vocalist is unmatched. There's just no one who can touch him in pop music that I've heard. Sorry, Freddie Mercury fans. Different ranges. Different, you know, we got baritone, we got tenor, we shouldn't come here.

But, you know, he just kind of stands alone, but one of the reasons for that is that he understood better than any other vocalist what that orchestration can do. Like, a great orchestration can literally make you sense. better than you are by a lot. And he didn't need that, but because he had it, it took an already great instrument and elevated it even further.

And I don't really think anyone understood that to the degree that he did. You listen to his recording of Laura, the Johnny Mercer, David Rackson song. And it's got like a minute-long intro with just the orchestra before Frank even comes in. And that's all Sinatra being, A, selfless and recognizing, you know, probably,

was a fan of the orchestra. When I walk into these sessions, whether it's an album recorder, whether it's something like the Orville, whether it's our show for Hulu, it's like, I'm walking in as a fan. Everybody who's in there is the best in the world of what they do,

and they're doing it together. Yeah. They're the Olympians of music. And it's exciting, and they're doing something that just seems impossible. Hmm. But you make it all possible. But what are you having to do to Channel Frank?

Like, do you have a wool suit? You got a glass of whiskey. Are we using his microphone? I don't go that far. That would be a tribute band. Yeah, there'll be a tribute band. It's, no, it's really about the sound and, you know, however you get there. It's about, you just got to be comfortable.

And I wonder how much of that he actually did as well. I know there are some photographs that have him all kind of dolled up for the camera. But I would question whether, I mean, like, it was the 50s, so everyone was a little bit more formal, the colored shirt. or gosh, R. I'm in a T-shirt. It wasn't wearing a hoodie. Yeah. But I do think that probably that once they got down to business, those doors shut. Right. And it was private, private, private. This is now work time. Yeah. And I'm sure it was, yeah, I'm sure the hat came off. But as far as interpretation, it's a combination of respecting the source material and knowing that this was written for him. Like, well, how would he have interpreted this and how would he have wanted this

interpreted and even more so how would Nelson Riddle or Billy May or Gordon Jenkins or Don Costa or any of these arrangers how would they have wanted interpreted that was really the big question that we asked vocally speaking you want to respect the music but at the same time it's like well I'm not just going to go in and do an impression like I'm going to try and find my own way into this because these songs don't exist the only thing where that was a little murky was lush life itself because half of the recording already existed and you could hear Frank kind of setting the style Life is lonely again And only

Last year Everything's seen But you know There's a point where that chart That recording just stops It's not only tough enough With the way it is But he's got some clides in there

There's no guidebook from there on that So it's like all right well Let's use the totality of the information that we have And try and make some art out of this Tell me about that song It's the title song. Yeah. And it has a different sound

than I feel like the rest of the record. We begin with a sort of ragtime piano. Yeah. It feels very old-timey. It feels like it was produced on a mono-old Victrola and then opens up. Yeah, that was deliberate in the arrangement.

That was Riddle mimicking the sound of multiple pianos playing in multiple parts of a walk through Paris at night, I think. Is this annotated in the charts? It is. It is. Somewhere, yeah. Joel is much better.

at explaining this than I am, because he really did a deep dive. But, yeah, that was, it was, Riddle at his most esoteric. And I think that that was one of the reasons that maybe it just wasn't, on that particular day, Frank just wasn't vibing with how complex this thing got. And, you know, on another day he might have, because he was certainly up to it. I mean, it was as sophisticated a chart as Riddle ever wrote. And there was no one more sophisticated than Frank as far as his vocalization. So he was definitely up to it.

I think he was just like, you know, I want to do something that's maybe a little more, a little more kind of universal. And, you know, it is Riddle stretching. And I'm sure to some degree, it probably broke Riddle's heart that it wasn't recorded because you can hear an artist playing with the boundaries of his art.

I mean, it's a pretty amazing piece for arranging. Life is lonely again. You're bringing back a lot of you. of Frank's music. I'm curious beyond his music if there's anything in particular from his life that you have taken his lesson into your own. It's been a great joy to get to know Tina Sinatra. That's probably the best way I can answer that. The lore that comes with Sinatra, you know, the tabloid drama that is so popular when it comes to any discussion of Frank Sinatra. I haven't ever really been drawn to that at all. There was a book that was written by Sinatra's engineer. I can't remember what it was called. I read it about eight or nine years ago. that was more interesting to me than any

of the Ava Gardner drama. It was the first time I had really had like a glimpse into the recording process, like how they made these, how these songs were recorded. And that's the real mysterious stuff to me. Were there any inside the studio things you take with you and your own work?

I remember reading, I remember reading that the first time he worked with Riddle, the arrangement that Riddle had written for him was maybe a little too, invasive. It was a little too hogging space that maybe it shouldn't have hogged. And Sinatra, as the story goes, had a talk with them and said, listen,

you know, do what you do, do your thing, but leave me some room so I don't have to holler over everything you're doing. And that does make, because, you know, with our records, Joel and I kind of, I think, had that same sort of revelation at some point, because we both love the orchestra and at a certain point, after the first album, I think we both thought,

there's a way to do this that's maybe a little bit slightly more balance where it's like less is more. Which Joel, as a film composer, you know, he kind of found his way into that naturally. Like the Jerry Goldsmith philosophy that like, yeah, you can write a thousand notes and you can overcook everything. But in many ways, if you can distill it down to the essence of what it is, your score sheets are going to look, they might look almost empty, but the sound that comes out of that orchestra is just so much more effective.

If you could give me three musical cues from the album and just, this happens makes me feel this or like brings about this sort of feeling. Yeah. I just want to sort of bring to life that diversity of sounds that we're hearing. I'm from Connecticut. We don't feel emotion.

Yeah, well, all right. Well, something like give me the simple life is a good example because it has every one of those Nelson Riddle kind of hooks, those things that he just went back to over and over the flutes that kind of have that little flutter that they do that are kind of constantly garnishing

what's going on in the chart with extra candy. I don't believe in, fretting and grieving, why mess around with strife? I never was cut out, two-step and strut out. Give me the simple life. Not so simple. That song kind of defies the story of Frank Sinatra in so many ways, right? You don't live a simple life.

You can see why maybe like, this is not. And the orchestration is not so simple. It's more of a Bing song. Like, that's a song that, like, you listen to it. This feels like something that Crosby would have sung and just kind of been like perfect for. But maybe the orchestration is telling us something that words aren't saying, right?

There's like, there's that productive descendants between the two. Yeah, it could be. But for me, it's what, that was one of the first ones we played in the first session and what was special about it was that it instantly was identifiable as a riddle chart.

And yet we had never heard it before. So he's like, there's no question who wrote this. And it has this familiarity and this comfort to it, but it's brand new. How about another cue? That, like, really different kind of sound? You know, Shadows is interesting. Shadows there on the wall.

Two shadows after day is done. Shadows is one of those songs on the record that also has the advantage of being a song that no one's ever heard. It's not just the chart. So, you know, for example, how did she look? There's a great E.V. Gourmet recording of that song. But Shadows is a song that no one's ever heard. That was written for the Moonlight So, Sinatra album in the early 60s, written for Frank, arranged by Riddle, and no one's ever heard it.

The arrangement or the song. And the same for Who's in Your Arms Tonight, which is the one that has the chorus. How do you get the feeling of shadows from the arrangement? What's happening in there for you? It's clearly a pop sound. It's clearly there's nothing artsy-fartzy about it. There's nothing that's too esoteric or asks the audience to have a season pass to, you know, the symphony. But it's truly orchestral and it's lush and it's got.

There's a lot going on in that. Shadow. Deep in a kiss. As through the night, their arms in twine. I can feel the shadows under the bridge. Yeah. It kind of glistens. Yeah, it glistened.

But there's that song. You know, Who's in Your Arms Tonight is interesting, because that's another one, that the song and the arrangement are completely unheard. Who's in your arms? And that one has a chorus, which sometimes Sinatra recorded with a chorus. There would be the orchestra, Sinatra, and then there'd be a chorus that would be included in the arrangement. And that was a whole other beast.

And the singers that did that for us really did their homework and really learned what it was that made that sound, that really tight sound. That's very selfless, where no one's trying to stick out. Nobody's trying to be heard. They just are trying to sound like one organism of voice. Beautiful stuff. Yeah, yeah. It's unique. It's really fun to talk with you.

I really appreciate you doing this with me. Yeah, you know, one day somebody will pay attention. It's been a lot of fun. Yeah. Thank you stuff for sharing. Yeah, sure. Switched on Pop is produced by Rihanna Cruz, edited by Art Chung, engineered by Brandon McFarlane, illustrations by Arras Gottlieb,

theme song by Jossi Adams and Zach Gennario of Arc Iris. Special thanks to Charlotte Tang for production support and Zach Mack for editing. We're a member of the Vox Media Podcast Network and a production of Vulture, which is part of New York Magazine. You can subscribe at NYMag.com slash pod. Find more episodes of Switched-on-Pop anywhere you get podcasts. And hit us up on social media at Switched on Pop. Tell us what you love about Frank Sinatra.

And maybe if you hear his influence in the sound of pop in the 2020s, we'll be back next week with a brand new episode. And until then, thanks for listen. Can we do it? How would Frank do it? Thanks for listening. Yeah. Daddyo.

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