Frank Sinatra Continues to Shape Pop Music

The Chairman's Enduring Revolution

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Picture this: It's the height of the grunge era, Kurt Cobain is reshaping rock music, and a college student at RISD walks into a record store and buys a Frank Sinatra CD. That student was Seth MacFarlane, who would go on to create Family Guy, and now, decades later, has become the unlikely custodian of Sinatra's musical legacy.

This pairing reveals something crucial about Sinatra's enduring power. Even twenty-seven years after his death, the Chairman of the Board continues to find new disciples in unexpected places. His innovations — flawless phrasing that sounds like natural speech, perfect intonation that predates Auto-Tune, the invention of the concept album — still shape how we make and hear pop music. His influence runs deep. Amy Winehouse titled her debut album Frank in direct tribute. Jay-Z calls himself "the new Sinatra." Frank Ocean borrowed his first name from the Chairman himself.

But MacFarlane's story goes beyond fandom. Through a friendship with Frank Sinatra Jr., his sister Tina, and the family's trust, MacFarlane gained access to over 1,200 boxes of never-recorded arrangements. The result is Lush Life: The Lost Sinatra Arrangements, an album that doesn't just honor Frank's legacy but extends it, proving that great art doesn't end with an artist's death.

Charlie: Could you walk me through the development of your relationship to Frank Sinatra, from your own personal relationship to the music?

Seth: My way into Sinatra's music was sort of a backdoor way. I was a big fan of orchestras, film music. I loved John Williams, I loved [James] Horner, I loved [Jerry] Goldsmith. I was listening to what 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.

When I got to college, I bought a Sinatra CD, went home and played it, and for the first time was hearing what was going on behind his voice. I was hearing what I loved about the film scores—this is a form of classical arranging. This guy's singing to something that's really sophisticated. So that was kind of how I found my way into his music—through the orchestra.

Charlie: What are your friends listening to? I mean, is this like peak Nirvana era?

Seth: Yeah, peak Nirvana era. So you know, Kurt Cobain, who's doing his own thing, singing a very different way. I'm over here listening to Frank. The thing about Sinatra is that there was always a place for him. You would walk down to the snack pit at RISD, and every once in a while somebody would be playing Sinatra on the jukebox. There was always kind of a space for him in the same way that there is now. He always kind of has his pocket of awareness.

Charlie: Your connection to Frank Jr. came through Family Guy?

Seth: I think I had seen Frank Jr. on The Sopranos 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. I was singing as Brian the dog in a sort of Sinatra-ish impersonation. Brian was my way into doing that stuff for a mass audience without really having to sing in a funny voice.

But it was fun because [Frank] was also a real scholar of this music. He turned 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 fifties and sixties that he introduced me to. And I went on and bought some records and I was like, "This is wild stuff."

Charlie: Tell me about Lush Life: The Lost Sinatra Arrangements. Why is now the right moment?

Seth: 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 Sinatra 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 a hundred charts that he had never sung. These were buried treasures that gave us the idea to make an album. One of the things that he did that was so great, which I've tried to take a cue 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. "Fly Me to the Moon," which was a ballad prior to his recording of it, he was the one that kind of turned it into this uptempo song, and that's obviously the arrangement that everyone knows so well.

Charlie: What was the process of unearthing them, making these selections?

Seth: 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. Because you don't really know what you have in there until you record it or until you play it. So we hired an orchestra, we went over to 20th Century Fox with 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? What's this?" That was really how we found the songs that we ended up putting on the album.

You're hearing things that were put to paper and in many cases, in most cases, never played. 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.

Charlie: What's the magic of the orchestra? What sort of emotional places does that take us?

Seth: Because of the diversity of sound you can get. You have an orchestra, you can do anything. 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.

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. That's something that's been kind of lost.

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

Charlie: I really love the arrangement for “How Did She Look”

Seth: "How Did She Look,” that seems to be everybody's favorite. First of all, it's 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 of what he was writing.

Only the Lonely was the sad concept album brought to perfection. 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. I wish Sinatra had sung this song because it would've been kind of epic.