By Nate Chinen of NPR

It has been 30 years since Harry Connick, Jr. became an improbable pop star, on the basis of a movie soundtrack that just happened to put many of his best features on display. If you know Connick at all, you might remember that album, When Harry Met Sally..., as some kind of watershed: a burnished vision of New York sophistication that renewed the American songbook for a dashing new cohort. Connick's first vocal entrance — on "It Had to Be You," set up by a momentous orchestral overture — conveyed all the ritual glamour of a leading man stepping from behind a curtain onto a proscenium stage.

Connick has a spruce new album, True Love: A Celebration of Cole Porter (Verve), that extends the sound and spirit of those early songbook triumphs. And he's now in residence on a proper stage — at the Nederlander Theatre, performing songs from the album in a Broadway show that he conceived and directed, and of which he's naturally the star.

There were no Cole Porter songs on When Harry Met Sally..., which went double platinum and won Connick his first of his three Grammy awards. But Connick has plenty of experience with Porter, whose blend of musical polish and wry lyrical sophistication made him a gold standard in the firmament of American popular song. While making True Love, Connick came to realize just how deeply deserved that reputation is, and how much nuance is needed to do justice to the material.

Connick talked about those welcome discoveries — and about balancing artistic ambition with commercial appeal, and the puzzle of orchestrating Porter's music, and much else besides — during a phone interview from his home in Connecticut. At 52, he retains the boyish enthusiasm that helped make him a household name, along with his New Orleans drawl.

NPR Music: The idea of Harry Connick, Jr. doing a Cole Porter songbook album feels like something that should have happened a long time ago. Do you feel that way?

Harry Connick, Jr.: I don't think it could've happened before, only because I wasn't really interested in doing it before. The problem with making records is, you have to pick. I guess I could have made this album, easily, 20 years ago. But I'll tell you what happened: I went in to meet with Danny Bennett, who was the head of Verve when I first started there. He's the guy who asked me if I would be interested in coming over there, because I had been with Columbia for a really long time. So when I met with him, he said, "What do you have in mind?" I said "Man, there's so many records I want to make. I want to make a New Orleans traditional album, I want to make a ballads album, I want to do all originals, I want to do another New Orleans funk album, I could do a gospel album." Among the choices, I said: "I want to do a Cole Porter tribute album," and his eyes kind of lit up. It doesn't really matter to me, because I'm so passionate about all these things. So when he said "Let's do Cole Porter," I said, "That sounds great." I had recorded a bunch of Cole tunes before, and obviously was very familiar with his music, but this was a legitimate, deep journey into this guy's brain, which I hadn't done.

There are many different people that you could focus on for a songbook album, but this is so apt, because the story of Verve begins with Ella Fitzgerald Sings the Cole Porter Songbook in 1956.

This is where I'm on a much lower platform than you. Now, I know that. But I had no idea that that's how Verve started. I mean, I knew Ella did a Cole Porter songbook album, but I didn't realize that was the start of it all. I didn't know it was her first record for Verve — and Verve's first record.

Right, and a very purposeful statement, trying to position her as a different kind of artist — with Cole Porter being sort of the Rolex choice. Do you have a relationship with that album?

I love that record, but I don't know it intimately. I probably heard every song on the record at some point in my life, but I haven't really listened to the music in a really long time. It's a record I obviously know. I wish I could say that I planned it that way, but I didn't know any of that stuff. A lot of people have done Cole Porter stuff. ... But there was just something about the fact that he wrote the words and the music, and had such deep musicality. But also just the songs themselves, I found, in their entirety, made a better collection for what I was trying to do.

There's something especially about the play of all his lyrical wit and sly humor, and then these musical decisions that often dovetail with that.

That's precisely right. And if you break it down into the three major elements of lyrics, melodies and harmonies, he did things that were unorthodox, he did things that were kind of incorrect. But he also did over-arching things that you don't necessarily notice the first 50 times you sing the song. Like when he did "True Love," which everybody thinks is just a very simple song, an AABA form. On the bridge he starts this super-long sentence:

For you and I have a guardian angel

On high, with nothing to do

But to give to you and to give to me

Love forever true

Most people would end [with] the thought: "For you and I have a guardian angel / On high, with nothing to do." Which is fine. But then he continues it on the last A section, which is really weird. It completely changes the nature of what he was saying, because on the bridge he's saying: "We have this guardian angel, but we're so in love we don't need him." However, he's the one that's making this happen for us. You could sing that song a hundred times, and go to the bottom of that trajectory, that sort of lyrical arc at the end of that bridge, and then lift up your delivery on the last A. But in fact, that's not what he's saying. He would do this stuff all the time. I could give lots of other examples; I'm sure you know them too. It's fascinating how this guy could be this master draftsman and do hyper-realistic paintings, and then the next painting he puts the ear on the back of the guy's head.

And I was going to ask about that song in particular, because so many Cole Porter songs are workhorses in the standard jazz repertory. But "True Love"...

Nobody plays that tune.

Yeah, it's from High Society, sung by Bing Crosby and Grace Kelly, and I know it as a movie song. I don't think I've ever heard a jazz musician play it.

Right.

So that raises the question of context. You've been on Broadway, Tony-nominated, and you've done other things in a theatrical context. So I wonder what perspective that brings, knowing that Cole Porter composed these songs for shows.

I think it adds a lot. But even more than my personal experience with theater, I think it actually comes from the way performers perform in New Orleans. There was always a sense of entertainment in the songs. Even though they were obviously freestanding songs, not songs meant to drive a plot forward. But the idea of using the songs as a piece of entertainment was something that was drilled into my head. Then when I started doing plays in high school, I started to see that not only were these songs advancing a plot, but the songs themselves were entertainment. It reinforced that when I started writing for Broadway and when I started acting on Broadway. It's not like I tried to make these songs sound particularly theatrical or cinematic, but the lyrics are driving everything. So the songs, if you look at the lyrics as little poems or pieces of prose, they determine everything. There is a theatrical quality about them. That's why, when I wrote this Broadway show, these songs are driving everything. Even though I'm not singing them how they were originally intended to be sung – like when I do "Why Can't You Behave," it's not a woman singing to her gambling boyfriend, it's whatever I want it to be – that's why those songs are so incredibly powerful. They're inherently so intact.

I want to ask about song selection. The album begins with "Anything Goes," which most people would expect to hear; "Just One of Those Things" is another one of those. But there are some interesting exclusions. You don't do "Night and Day." You don't do "Ev'ry Time We Say Goodbye." Then there are other selections, like "Why Can't You Behave," that are a little more obscure. What was your criteria for putting this song list together?

What I did was, I went through and played the songs. The basic criteria for me, it was always lyrics. 'Cause some of these songs — like "You're Sensational," it's tough to have music be relatable when the references are from another generation. Like, when he writes "I don't care / If you're called 'The Fair Miss Frigidaire,' " that's great, but when you're singing to an audience, for two seconds, 90% of the people don't know what you're talking about. That's not what you want. Every single word matters. I tried to pick tunes that had great lyrics for me, and then I looked at the melodies, and these melodies I responded to. So I could have done "Ev'ry Time We Say Goodbye," or "Night and Day," but I had to pick. And I just picked ones where I said "Oh, I know what I want to do with this."

You also included "I Concentrate on You," and it's impossible for me to tune out Sinatra when I hear that song.

Oh, right.

And Frank has meant a lot to you. Are you thinking about previous interpretations at all as you're recording this material?

So, Nate, you can believe this or not, but I'm telling you the truth: Not at all. Not in the least. OK, I'll be honest with you — there was one point on the record where I intentionally tried to do something because I wanted to see if I was right. It's in the shout chorus of "True Love," when the saxophones do this complete and utter blatant reference to Billy May. When they go "Booo-dah," and there's a big drum fill, and then "Booo-dah." I always wanted to know, "How does Billy May do that?" I was thinking about that and I said "Oh, OK, he's going to take one alto saxophone and one tenor saxophone on the high part, and then, a major sixth lower, he's going to do another alto and a tenor. I wonder if that's how he did it." And then when I got in the studio, I said, "Ah! That's how he did it." My dad heard that, he said, "That's Billy May." And I said "It actually is."

I'm sure I've heard Sinatra sing that song a thousand times. And I'm sure that he as well as so many singers have influenced me. But it's so far back now that I didn't think about it. ... Was Sinatra a direct influence on me? Maybe at some point, but not anymore.

You alluded to something important in that answer, which is the extent to which you are a mechanic of big-band orchestration. That's distinct from a lot of other people who sing these songs. You have a sort of holistic understanding of what's happening on the bandstand, and I feel like you absolutely have a recognizable style as an orchestrator.

Oh, that's cool.

It sounds to me like that awareness, of what the band is going to do, is guiding you — maybe not as much as the lyrics, but it's in there. It's important.

Oh, yeah. It's huge. That's really astute, and I can honestly say that no one's ever really said it that way. It's absolutely true. There's so much nuance. We're not talking about arranging the songs where you say "doo-dee, doo-dee," and go give it to an orchestrator. We're talking about sitting down with a blank piece of score paper and literally writing every note, every articulation, every phrase marking, every dynamic — all of that stuff. And that takes an immense amount of time. As you build these motifs and these counter-melodies — because essentially that's what these arrangements are. I mean, you listen to any tune, and they all have new melodies in the introductions that are inspired by the idea of the song, but they're new melodies just like you make up new melodies when you improvise. When you start to massage the nuance from the orchestra, I'm keeping in mind that in an hour, I'm going to be singing these tunes. So how they play them, and the specificity of the tempos and the keys, and the dramatic effect that you get when you push yourself out of your own vocal range – all of that stuff. It's the greatest luxury in the world, because it's not a committee.

Were there any puzzles to work out with a particular song, as you're getting into the balance of orchestration and vocals?

Well, I realized something on this record that I didn't really know before, and I'm embarrassed to say it took me this long. High art and accessibility are not mutually exclusive. So, as much as I've always wanted to be successful – and to me that means having the ability to go in the studio and record whatever you want to record, and having an audience to perform it for – having that, and at the same time maintaining the highest quality of musicianship, was always a difficult fence to straddle. Because people are paying for these tickets. And you're performing for them, and you want to give them something, but you can't for a minute think about that when you launch into an eight-chorus solo. It would change the way you play. So I would love the idea of manipulating the listener so it was just uncomfortable enough to create this musical tension that could then be released by something more accessible. I've thought of those two things as separate. And for this album, I think I finally figured out how to merge those, 50-50. The only way to describe it is like this: When the musicians come up to you and say "Damn, bro."

Dan Higgins, the most in-demand reed player in L.A., played second alto on this album, and he came up to me and said: "Man, all these other arrangers would just do variations of the melody on the shout. I've never heard this before." I hope it doesn't sound braggadocious to say it like that, but when you can have a musician tell you that? Or when one of the musicians tells me he's playing a wrong note. I say "Hey man, bar 82, on the 'and' of three, it needs to be a half-step higher." He goes: "Oh, you wrote an errant D-flat, I changed it to a D natural." And I say, "Actually it's not errant at all, it's supposed to be a D-flat." When you start hearing stuff like that, you're basically saying that the musicians are hearing something that they're not expecting to hear.

And at the same time, I played this music on Good Morning America, and there were 30 high-school girl soccer players there that day. I don't know if they're ever heard real musicians play, let alone a Cole Porter song, and they were smiling. And I said, "OK, that's how you do it." There's a way to have all of that stuff going to you, and have it be interpreted on all these levels.

To a large extent, your career has always been about balancing an entertainment impulse with, for lack of a better term, a high-art aspiration.

That's exactly right.

And you've been on Broadway twice before with a show like this. I watched your 1990 special many times on VHS, and then I saw your show in 2010. What both of those shows had in common was your physicality, which I think comes out of that New Orleans impulse.

Right.

You are not someone who stands rooted to the spot, static. That has not been your approach. And it always struck me that you were ferociously determined to bring the audience with you, and you were going to do whatever it took, even if it took running across the length of the stage. That's a killer show business instinct...

That's really close, but there's a slight variation to it. Part of me wants to do whatever it takes. The other part is doing things I'm compelled to do — there's something about being onstage that just makes me feel alive in a way that I don't feel offstage. Lemme just say this: that's really, really close. That's a really accurate description. I remember going on tour once in Europe, and I'd change the show every night, so I'd play some instrumental tune, and then I'd sing a tune and the show would go on. One night I came out and played two instrumental tunes. And one night I played three. And I remember in Switzerland there were like, eight instrumental tunes before I even started singing, and my tenor player at the time, Ned Goold, was loving it. He said, "What are you trying to do, make the people leave?" And I'm like, "No, let me see how far we can push them to things they're not familiar with, and them bring them back. Just by doing a different version." 'Cause like, man, when I play a solo in the middle of some tune, the last thing I'm thinking about is, "Do the people like it?" But you have to get there. And how do you get there without changing anything? So that forces you to say, "How do I play and write and sing in a way that is truthful to both camps?" I guess that's what I was saying before: it took me a while to figure that out.

To that end, I think it's important that you put the piano in the foreground at points on this album, like on "Begin the Beguine." It wouldn't be true to you otherwise.

Yeah, and I think on two tunes, there's other people playing solos. But my co-producer, Tracey Freeman, who I've known since high school, said: "Man, don't give solos to anybody else on this record. Play on every tune."

With a crucial Lucien Barbarin exception, though.

I had to make an exception for Lu. [Laughs] He's a god.

As we talk about entertainment and art, and how they converge — you said something in your earlier conversation with NPR, about how the reason to sing these songs is simply quality. It's not about time travel; it's this everlasting excellence of these songs.

That's right.

So I wanted to ask whether you feel, celebrating these songs, that there's a kind of endangered-species feeling. Do you feel like you're swimming against the current, in terms of popular music?

Well, if you look at it that way, I've always been doing that. This music hasn't been popular in my lifetime. It's what I believe. I mean, I believe other things, but I happen to believe that there's a place for this music. What's changed since the 1990s is the other music. Like, it's gotten to the point now where, not to be punny about it, but "Anything Goes." And I mean, anything goes. So I don't feel like I'm in Jurassic Park with these tunes. I really believe that on this album, and even more so in the context of this Broadway show, I don't care how old you are. And I don't care if you've never heard this music before. You will hear these lyrics, and you can't help but be like, "Wow, that's amazing." I'm just talking about the songs, not my performance of them. So am I swimming against whatever? Yeah, I guess, but that never entered my mind. I've always done kind of what I wanted to do.

More than most people who sing these songs regularly, you've had up-close and in-person experience working in a more popular-music vein — and you've also made music that, for lack of a better category, would be filed under "pop." You haven't had blinders on.

Right. But I wasn't doing those things because I was trying to be a part of something. I did those things because... I mean, I actually have had blinders on. Because I've just done things that I really felt like doing. There's never been a committee. Except when I did this one record with Clive Davis, which was something I wanted to experience. I wanted to experience having somebody else's opinion in the room. I almost didn't make it through the process, but it was something I committed to because I wanted to understand what that was. I didn't know what a producer was. And I'm like, "What do these people do?" So, 25 albums into my recording career, I found out what producers do. Oh, can I answer one more thing about the last question?

Please do.

You know what's changed since the '90s? Moving bass lines. They don't move anymore. They're literally these pedal tones. And the other thing, it's the idea of any kind of backbeat or snare drum. You turn on any pop radio station right now, I promise you will not hear a snare drum on 2 and 4. It's either going to be a handclap or a finger-snap or some very small sound. It's gone so far that I think there's a novelty now, not because of the genre but because of the way the instruments are playing. It's really kind of wild.

You mentioned this immersion you had in Cole Porter's music. Can you give me an example of some kind of revelation you had?

There's a song called "Mind If I Make Love to You," which is also from High Society. It's from a scene in the movie where Frank Sinatra sings to Grace Kelly. So I go through this sheet music, because I want to know what harmonies and melodies he intended. I started looking at how Cole Porter did stuff that you just don't do, technically speaking. Usually you go from a major-seventh chord to a dominant-seventh chord; that's how that kind of works. But he goes the other way. [Sings]: "Dawn is nearing, time is fleeting" — when he says "time," that means not only do I have limited choices... Like, people talk about Frank Sinatra's phrasing all the time. Nobody ever really talks about what that means: What that means is, he's accommodating the content of the lyric, and that directly depends on orchestration. You can't hold a note for emphasis and not understand what's going on harmonically beneath you. You can't hold a note over the bar unless you know what the first chord of that next bar is. Whether you can articulate it or not, you have to be able to know that that note you're holding is a common tone between two chords.

Right.

So when Cole Porter wrote that melody, he doesn't give you any choices. Like, the next part of the process for me is to arrange and then orchestrate it. I'm looking at the strings and going, "Wow, man, he just put roadblocks up everywhere." If I want to sing this melody authentically, I only have a couple of choices. And now, what am I going to do lyrically? What if I want to hold "Dawn is nearing, tiiiiiime is fleeting"? I can't. As the arranger, I could say, "Well, if I decide on the day to hold that note, maybe I'll change the arrangement now." But then, what are you doing, bro? When you sing it, you're just going to sing it. So those are the types of challenges that Cole Porter presents. They're super subtle. Maybe one day I'll sit down at the piano and we can go over this. It's really interesting, but 99 out of 100 people are like, "I have no idea what you're talking about."

Well, the way you're describing it, they're subtle but they're architectural.

They're completely architectural. They are completely practical in the sense that he was intentionally creating tension that he could then release. But because he was such a musician... I went to the Yale library. Did you know about this guy's orchestration skills? Like, I had no idea he could orchestrate. Legitimately, for an orchestra. There are big, giant manuscript papers with his scoring. I was like, "Oh, OK, now this makes sense." Because you can't get the melody, the lyrics and the harmony to line up like that intentionally without knowing every aspect of all of them. That's the kind of stuff where I was like, "Man, this dude was really on a high level."

I wanted to wrap up with lyrics. As you alluded to, some of the sexual politics are certainly out of date in some of these songs. But you're going to be on Broadway, and you were celebrated for a role in The Pajama Game, which is another example of a throwback sensibility, which skews sort of playfully naughty. How much does the experience of being in a show like that inform this one?

Well, the major difference is that I'm playing a character. And now, when I sing "All of You," which is one of the more suggestive songs this side of modern hip-hop music...

Yes — and let me just say that when you sing "The east, west, north and the south of you," the way you land on the word "south" is super dirty.

Oh, it's dirty. There's other things in there, too. Like the thing about "love at least a small percent of me." But when I'm singing that song, not only am I aware of the climate we have, but I'm also aware that that climate has allowed people to think of themselves differently, too. So I'm not necessarily singing autobiographically, or from a personal perspective. This could be anybody's perspective. It could be anything. So that's what's amazing about it. When I sing that song in the show, there's a reason I did it that slow. It's supposed to make you uncomfortable. But what a luxury it is to have Cole Porter write that, so articulately, and I get to drive the Ferrari for a while. And yet, still appear sensitive — which I am, in my personal life — to all of the incredibly important issues that we have. So it's really interesting that a song that's however many decades old could still make people think about that.

This interview was edited for length and clarity.