Ever since “What You Won’t Do For Love” first catapulted him to stardom in 1978, Bobby Caldwell has cultivated a singular brand of sophisticated soul, culminating in more than a dozen studio albums that have as well embraced aspects of pop, jazz, and big band standards along the way.
On the recently released LP, Cool Uncle, he’s collaborated with GRAMMY®-winning producer Jack Splash (Kendrick Lamar, Jennifer Hudson), summoning moments that are at once urban and sumptuously urbane. Featuring cameos from the likes of CeeLo Green, Mayer Hawthorne, and Jessie Mare, the album is primed to broaden Caldwell’s audience while at the same time satisfying his music’s most ardent connoisseurs.
With the Cool Uncle album, what did you guys initially hope to achieve? What was the goal?
Initially the goal was to write for other artists, but it quickly kind of morphed from that into something entirely different. It was Jack who came up with the idea about, “Why don’t we make us the entity and give it a name and use it as a vehicle not only for us but for other artists to participate, not only on the current album but future albums?”
Did you have an idea for how you wanted this album to sound? I’ve read something in which you said you didn’t want it to sound like what you were already known for.
You’re absolutely right about that, and maybe 50 percent of the success was me getting out of my own way and letting Jack do what he does best. Once you establish the roles of the players, you’re probably better off if you understand what each person is going to be doing. Because when you get too many chefs in the kitchen, it’s usually a disaster.
You’ve always struck me as an artist who enjoys stepping out of your comfort zone a little bit to see what that yields.
That’s a real good point, man. I kind of knew that going in, that I was going to be out of my so-called comfort zone. When it comes to something like that you’ve just got to embrace it. And, like I said, letting Jack do what he does best and him letting me what I do best is really why it all came together, I think.
Considering the eclecticism of your career insofar as the styles and genres you write and record in, is there a place where you are not so much complacent, but most comfortable?
Geez, that’s a tough question. I’ve never thought about it in terms like that.
Do you know what you do best?
Yes, I do. Look, yeah I do know what I do best and I know what I can’t do best. I’ve never lived the Black experience. So, I leave that to people who have, who know about it, who’ve lived it. I’m just a fan of some of the greatest Black artists of all time, and I’m sure we’d agree on who those are. I [am], basically, a white guy from the South doing what he does that’s been influenced by all of those things. I don’t think anybody in this world is original. We’ve all stolen from somebody. We’re like the sum total of our influences. But I don’t know anybody that tries to do what I do, but I’ve been guilty of trying to do what other people do.
You quickly come to realize … what you do best and try to stand out of your own way, because sometimes you get so close to these projects you can’t see the forest through the trees. This is when it’s nice to have a team because often times Jack would lure me out of some kind of thing that I was on that was leading nowhere and vice versa. We’re constantly checking each other, and that’s a good thing. The way it all comes together at the end of the day is just incredible.
White artists who’ve recorded and performed traditionally Black music have often had to prove themselves to a Black audience — maybe in ways they would not have had to prove themselves to a mainstream white audience — but once they did so they were not only accepted but were shown incredible loyalty. I wonder if that has been your experience as well.
It’s absolutely been my experience, and still is. A lot of people misunderstand what were the Black radio listeners, who they really were. They grew up and got married, had kids, and those kids are basically inner-city and they listen to their folks’ record collection and they get turned on to this old stuff, too. I look out at my audience and I see three generations of people, which is … about how long I’ve been going, a little over 35 years.
Going back a little further, for someone who was a teenager and came of age in the era of the Beatles and the Stones and Motown, where did your appreciation come from for Frank Sinatra and Tony Bennett and Nat “King” Cole?
That came from my folks. They were in the theatre, and had a television show in the early ’50s out of Pittsburgh. I was always surrounded by Ella Fitzgerald music, Sinatra, Tony Bennett, Nat “King” Cole, the big band stuff. That was a great environment for me to grow up in, [along with] an appreciation for songs and those singers of the day. It wasn’t by choice. It was just something I was inundated with. I lived in Sinatra headquarters. That was all I heard, twenty-four/seven save for the music I hid away with in my room.
Man, I was exposed to so much stuff. You just named a few things, but growing up in Miami I was exposed to reggae and ska, Calypso music. We had a couple of serious R&B stations, and I believe they’re still there, if I’m not mistaken. WEDR was one of them, [and] WMBM in Miami Beach. They played just the stone-cold Philly/Motown/Muscle Shoals, all that shit. We had back then, basically, the Hot 100 that is still around today, but, see, in that Hot 100 there was all kinds of stuff. I mean, you’d see Sinatra songs, you’d see Beatles songs, you’d see Four Tops, you’d see Temptations. It was all over the map.
All modesty aside, you must have at some point recognized that you had the goods and the talent to sing the music you most enjoyed. Was there some moment or epiphany or experience that convinced you that you could not only appreciate all that great music but sing it too?
Just to get there you’ve got to believe in yourself, but a lot of times along the way that belief gets shaken sometimes to the core where you just think, I’m not going to make it. It’s just not happening for me. There’s always that struggle. It was like rolling the dice, and I didn’t actually know until after the first album did what it did.
Really? You didn’t know you had something with that first album when you finished it, before you released it?
No, I didn’t know who I was, where I was headed with the music. I just kind of let it take its own direction. So, when I say “until after the first album did what it did,” in a lot of respects it’s the record-buying public, the fans, who determine — now, I’m talking about first-time artists — who you are, and you get anointed with this “blue-eyed soul brother” [label]. It took years for everybody to finally realize that I wasn’t Black. That was the least of my problems. [Laughs] But it was really them; they determined who I was. That was great, to have that validation: “This is a bad boy.” To have that, you’re pretty much on a course as long as you don’t fuck it up, and that happens too.
Despite what you looked like when you walked out on stage, though, people recognized that there was something special about those songs on that first album that could perhaps evolve into something even more special on subsequent albums.
I’d like to think it did, yeah. Then again, the first album was so, so huge, not just in the States, but globally. It was massive. A lot of artists — and this in some respects is definitely true for me — they get this brand of “one-hit artist,” and I just kept on releasing the best albums I could. Oddly enough, it was only with other artists that I achieved the same sales numbers.
You mean in writing for the likes of Boz Scaggs [“Heart of Mine”] and Chicago [“What Kind of Man”]?
Yeah. That’s why, actually, I started writing for other artists because my sales… When you go from selling five million albums to, like, selling 150,000, you’ve got a problem. And so I left Miami and I went to L.A. and I started making the rounds with other songwriters. Fortunately, for me, I had already earned a lot of their respect, having that massive song that was still fresh in everybody else’s mind and still is today. So, I got into these circles and it was just a great bunch of people all with great track records as writers. I got very fortunate with about four to five years of doing that, and then I picked up my mantle again and started making more Bobby Caldwell records.
Geez, that’s a tough question. I’ve never thought about it in terms like that.
Do you know what you do best?
Yes, I do. Look, yeah I do know what I do best and I know what I can’t do best. I’ve never lived the Black experience. So, I leave that to people who have, who know about it, who’ve lived it. I’m just a fan of some of the greatest Black artists of all time, and I’m sure we’d agree on who those are. I [am], basically, a white guy from the South doing what he does that’s been influenced by all of those things. I don’t think anybody in this world is original. We’ve all stolen from somebody. We’re like the sum total of our influences. But I don’t know anybody that tries to do what I do, but I’ve been guilty of trying to do what other people do.
You quickly come to realize … what you do best and try to stand out of your own way, because sometimes you get so close to these projects you can’t see the forest through the trees. This is when it’s nice to have a team because often times Jack would lure me out of some kind of thing that I was on that was leading nowhere and vice versa. We’re constantly checking each other, and that’s a good thing. The way it all comes together at the end of the day is just incredible.
White artists who’ve recorded and performed traditionally Black music have often had to prove themselves to a Black audience — maybe in ways they would not have had to prove themselves to a mainstream white audience — but once they did so they were not only accepted but were shown incredible loyalty. I wonder if that has been your experience as well.
It’s absolutely been my experience, and still is. A lot of people misunderstand what were the Black radio listeners, who they really were. They grew up and got married, had kids, and those kids are basically inner-city and they listen to their folks’ record collection and they get turned on to this old stuff, too. I look out at my audience and I see three generations of people, which is … about how long I’ve been going, a little over 35 years.
Going back a little further, for someone who was a teenager and came of age in the era of the Beatles and the Stones and Motown, where did your appreciation come from for Frank Sinatra and Tony Bennett and Nat “King” Cole?
That came from my folks. They were in the theatre, and had a television show in the early ’50s out of Pittsburgh. I was always surrounded by Ella Fitzgerald music, Sinatra, Tony Bennett, Nat “King” Cole, the big band stuff. That was a great environment for me to grow up in, [along with] an appreciation for songs and those singers of the day. It wasn’t by choice. It was just something I was inundated with. I lived in Sinatra headquarters. That was all I heard, twenty-four/seven save for the music I hid away with in my room.
Man, I was exposed to so much stuff. You just named a few things, but growing up in Miami I was exposed to reggae and ska, Calypso music. We had a couple of serious R&B stations, and I believe they’re still there, if I’m not mistaken. WEDR was one of them, [and] WMBM in Miami Beach. They played just the stone-cold Philly/Motown/Muscle Shoals, all that shit. We had back then, basically, the Hot 100 that is still around today, but, see, in that Hot 100 there was all kinds of stuff. I mean, you’d see Sinatra songs, you’d see Beatles songs, you’d see Four Tops, you’d see Temptations. It was all over the map.
All modesty aside, you must have at some point recognized that you had the goods and the talent to sing the music you most enjoyed. Was there some moment or epiphany or experience that convinced you that you could not only appreciate all that great music but sing it too?
Just to get there you’ve got to believe in yourself, but a lot of times along the way that belief gets shaken sometimes to the core where you just think, I’m not going to make it. It’s just not happening for me. There’s always that struggle. It was like rolling the dice, and I didn’t actually know until after the first album did what it did.
Really? You didn’t know you had something with that first album when you finished it, before you released it?
No, I didn’t know who I was, where I was headed with the music. I just kind of let it take its own direction. So, when I say “until after the first album did what it did,” in a lot of respects it’s the record-buying public, the fans, who determine — now, I’m talking about first-time artists — who you are, and you get anointed with this “blue-eyed soul brother” [label]. It took years for everybody to finally realize that I wasn’t Black. That was the least of my problems. [Laughs] But it was really them; they determined who I was. That was great, to have that validation: “This is a bad boy.” To have that, you’re pretty much on a course as long as you don’t fuck it up, and that happens too.
Despite what you looked like when you walked out on stage, though, people recognized that there was something special about those songs on that first album that could perhaps evolve into something even more special on subsequent albums.
I’d like to think it did, yeah. Then again, the first album was so, so huge, not just in the States, but globally. It was massive. A lot of artists — and this in some respects is definitely true for me — they get this brand of “one-hit artist,” and I just kept on releasing the best albums I could. Oddly enough, it was only with other artists that I achieved the same sales numbers.
You mean in writing for the likes of Boz Scaggs [“Heart of Mine”] and Chicago [“What Kind of Man”]?
Yeah. That’s why, actually, I started writing for other artists because my sales… When you go from selling five million albums to, like, selling 150,000, you’ve got a problem. And so I left Miami and I went to L.A. and I started making the rounds with other songwriters. Fortunately, for me, I had already earned a lot of their respect, having that massive song that was still fresh in everybody else’s mind and still is today. So, I got into these circles and it was just a great bunch of people all with great track records as writers. I got very fortunate with about four to five years of doing that, and then I picked up my mantle again and started making more Bobby Caldwell records.
After having that massive success with that first album, and with people associating you with one type of music, was it difficult to then later on venture into recording the standards albums [1996’s Blue Condition and 1999’s Come Rain or Come Shine]? Did you think you might alienate your audience?
No, because my desire to do it was so strong, and I knew that at some point in my life I had to do this. It was something that was really comfortable — to point out one of your previous questions, a comfort zone — and I felt I could do it as good if not better than the handful of other people that were doing it. At that point in time it was Natalie Cole, Harry Connick, Jr., Brian Setzer; they were doing this stuff. I did it on two albums, and it was great. I got a whole new audience and managed miraculously to keep my [existing] audience who came along for this ride and loved every minute of it.
Is it hard to shift gears when you’re on tour, doing the different shows?
No. It’s really fun. It’s great. When I’m out doing the orchestra, the big band, it’s a great departure to get away from the R&B even if it’s for a second. Once you’ve come to know the power of a 16-piece big band or an 18-piece big band, it’s stunning. There are actually people onstage moving air instead of synthesizers and all that stuff. It’s a whole different vibe.
And you’re not stumbling over speed bumps trying to transition between the two.
No, and I will tell you something that I’m adamant about, and that is that if I’m appearing somewhere with the orchestra, wherever it’s advertised whether it’s in print or on radio, I make sure that people know it’s the orchestra. When I first started doing this, there were a couple of shows where people would come out thinking they were going to be hearing the orchestra and vice versa — people thought they were going to be hearing R&B. So once I got over that hurdle, albeit small, the same fans show up, man. I’m telling you, it took some doing, but they come in droves whether it’s R&B or the orchestra. I’ve been really fortunate that way. Obviously I do more R&B shows than the orchestra, and doing the orchestra, it’s not cheap. Gone are the days when Benny Goodman used to get on a bus with all his players and go from state to state without taking showers and stuff. [Laughs] Those days don’t even exist anymore.
I remember Barry White would tour with his core band and then — to fill out the Love Unlimited Orchestra — he’d use local players.
Well, I do that with the orchestra. In other words, I’ll take my key players, like the drums, the bass, and keyboards, and I’ll hire what people call the A-players in any given city. As long as they can read music, the charts are there for them to read.
Do you rehearse with these musicians in each city, then?
Yes, and that’s also a cost. Also you’re dealing with different unions — they all have different rules in every city — and they can be tough.
There’s more to what you do than what you do onstage.
Oh yeah. Absolutely.
Does songwriting come relatively easy for you? A lot of songwriters I’ve spoken to love the finality and the accomplishment of having written a song, but hate sitting in a room and actually grinding it out. Do you enjoy the process?
I’ve got to be totally honest with you, man. In my early career, it was just so passionate, just something I would always look forward to doing. But at some point, you have kids, you get married or whatever it is you do — I did all of that — and everything starts to change. Priorities start to change. Now, it’s become grinding them out. I’m kind of on a treadmill that I can’t get off of. I’ve got twin daughters, they’re 23. I’ve got a stepdaughter, she’s 24. I’m fucking surrounded by women. Everything changes, that’s all I can tell you. Do I like it when something great has happened or I’ve done something great? Sure. But, I tell you what else, doing a project and finishing, completing the work, I let it go. You have to let it go.
In what sense?
When I say I let it go, if it does well and it’s a success I’m pleasantly surprised. If not, I’m not in total despair.
So, you’re not anguished over whether it’s number 10 on the charts or number 14.
No. No, I gave that up a long time ago. Look, I’ve got to tell you, man, you’re old enough to know that 20 years ago a normal platinum, really smash album — we’re talking about Universal, MCA, Columbia, any of those major labels, Warners — they were celebrating, like, 20 million sold. Now, they’re dancing in the streets over a million. This is how screwed up everything’s gotten, not just their numbers, but this intellectual property issue with the downloads. This is serious shit and it’s never going to change now.
It’s not going to go in the other direction, that’s for sure.
No, it’s not. Although, for myself and so many other artists, we blame the labels because they had the chance to fend this off with coding the product, but they thought Napster was going to go away. It did go away; it just moved into international waters and all of a sudden all of these other things started popping up like a cancer.
Do you ever gain new insight when you hear someone cover one of your songs?
No, not necessarily. I kind of anticipate how they’re going to do it because I wrote the song for them.
You wrote “Heart of Mine” specifically for Boz Scaggs?
I did initially write the song for Boz. It didn’t end up that way. It kind of went around and around. It was going to be on the Chicago album, then it wasn’t. Then Boz did a demo of it that I thought was fucking great. I don’t know whatever happened to that. Then he lost interest. Then he did the song again, and had a number one adult record with it. It went through a lot of changes. But when he did it, it sounded like Boz to me. There’ve been some surprises, like Go West doing “What You Won’t Do For Love,” that surprised me. I wasn’t expecting that at all.
When you wrote “What You Won’t Do For Love,” you couldn’t have anticipated the amount of people who would cover it.
No, I didn’t think it was going to be a hit record. I had my eye set on something else on the album. I was wet behind the ears. I didn’t know shit, but what was about to happen was just insane. And what kept happening, all the covers of that song, I never would’ve predicted that.
Is that something you appreciate, the covers and the samples?
Oh yeah. I get asked if I get tired of performing the song or hearing the song, but every time I perform it the audience makes it feel like the first time. So I’m appreciative of that and that it even happened to begin with. When that album was done and it slowly made its way up the charts, my dear friend Natalie Cole had a number one record with her debut album. She was number one on the Hot 100 and I was, like, number nine trying to get up into the top five. She called me one day and was embarking on her first tour. At this point I was looking for something to happen, regarding full-scale performing where I could get all over the country. This was perfect for me, the audience. It was a mix. Obviously, there were more Blacks than whites. It was a good mix, let’s say 6,000 Blacks [and] 2,000 whites, something like that. So, most of the people are coming out to see “soul brother” Bobby Caldwell. The first show was in Cleveland. When I came out on that stage to open for Natalie, you could hear a pin drop. It hadn’t even occurred to me, “What’s going to happen when they see I’m white?”
Did you know before the tour that people perceived you as Black?
Oh absolutely. Everything was pointing in that direction. Most of the radio personalities didn’t know. Some of them did.
That goes back to what I said earlier, though, that once you prove yourself they’ll accept you.
Yeah, and I think you said earlier, Black audiences are loyal to the core. They’re not going to, like, unfriend you.
.
No, because my desire to do it was so strong, and I knew that at some point in my life I had to do this. It was something that was really comfortable — to point out one of your previous questions, a comfort zone — and I felt I could do it as good if not better than the handful of other people that were doing it. At that point in time it was Natalie Cole, Harry Connick, Jr., Brian Setzer; they were doing this stuff. I did it on two albums, and it was great. I got a whole new audience and managed miraculously to keep my [existing] audience who came along for this ride and loved every minute of it.
Is it hard to shift gears when you’re on tour, doing the different shows?
No. It’s really fun. It’s great. When I’m out doing the orchestra, the big band, it’s a great departure to get away from the R&B even if it’s for a second. Once you’ve come to know the power of a 16-piece big band or an 18-piece big band, it’s stunning. There are actually people onstage moving air instead of synthesizers and all that stuff. It’s a whole different vibe.
And you’re not stumbling over speed bumps trying to transition between the two.
No, and I will tell you something that I’m adamant about, and that is that if I’m appearing somewhere with the orchestra, wherever it’s advertised whether it’s in print or on radio, I make sure that people know it’s the orchestra. When I first started doing this, there were a couple of shows where people would come out thinking they were going to be hearing the orchestra and vice versa — people thought they were going to be hearing R&B. So once I got over that hurdle, albeit small, the same fans show up, man. I’m telling you, it took some doing, but they come in droves whether it’s R&B or the orchestra. I’ve been really fortunate that way. Obviously I do more R&B shows than the orchestra, and doing the orchestra, it’s not cheap. Gone are the days when Benny Goodman used to get on a bus with all his players and go from state to state without taking showers and stuff. [Laughs] Those days don’t even exist anymore.
I remember Barry White would tour with his core band and then — to fill out the Love Unlimited Orchestra — he’d use local players.
Well, I do that with the orchestra. In other words, I’ll take my key players, like the drums, the bass, and keyboards, and I’ll hire what people call the A-players in any given city. As long as they can read music, the charts are there for them to read.
Do you rehearse with these musicians in each city, then?
Yes, and that’s also a cost. Also you’re dealing with different unions — they all have different rules in every city — and they can be tough.
There’s more to what you do than what you do onstage.
Oh yeah. Absolutely.
Does songwriting come relatively easy for you? A lot of songwriters I’ve spoken to love the finality and the accomplishment of having written a song, but hate sitting in a room and actually grinding it out. Do you enjoy the process?
I’ve got to be totally honest with you, man. In my early career, it was just so passionate, just something I would always look forward to doing. But at some point, you have kids, you get married or whatever it is you do — I did all of that — and everything starts to change. Priorities start to change. Now, it’s become grinding them out. I’m kind of on a treadmill that I can’t get off of. I’ve got twin daughters, they’re 23. I’ve got a stepdaughter, she’s 24. I’m fucking surrounded by women. Everything changes, that’s all I can tell you. Do I like it when something great has happened or I’ve done something great? Sure. But, I tell you what else, doing a project and finishing, completing the work, I let it go. You have to let it go.
In what sense?
When I say I let it go, if it does well and it’s a success I’m pleasantly surprised. If not, I’m not in total despair.
So, you’re not anguished over whether it’s number 10 on the charts or number 14.
No. No, I gave that up a long time ago. Look, I’ve got to tell you, man, you’re old enough to know that 20 years ago a normal platinum, really smash album — we’re talking about Universal, MCA, Columbia, any of those major labels, Warners — they were celebrating, like, 20 million sold. Now, they’re dancing in the streets over a million. This is how screwed up everything’s gotten, not just their numbers, but this intellectual property issue with the downloads. This is serious shit and it’s never going to change now.
It’s not going to go in the other direction, that’s for sure.
No, it’s not. Although, for myself and so many other artists, we blame the labels because they had the chance to fend this off with coding the product, but they thought Napster was going to go away. It did go away; it just moved into international waters and all of a sudden all of these other things started popping up like a cancer.
Do you ever gain new insight when you hear someone cover one of your songs?
No, not necessarily. I kind of anticipate how they’re going to do it because I wrote the song for them.
You wrote “Heart of Mine” specifically for Boz Scaggs?
I did initially write the song for Boz. It didn’t end up that way. It kind of went around and around. It was going to be on the Chicago album, then it wasn’t. Then Boz did a demo of it that I thought was fucking great. I don’t know whatever happened to that. Then he lost interest. Then he did the song again, and had a number one adult record with it. It went through a lot of changes. But when he did it, it sounded like Boz to me. There’ve been some surprises, like Go West doing “What You Won’t Do For Love,” that surprised me. I wasn’t expecting that at all.
When you wrote “What You Won’t Do For Love,” you couldn’t have anticipated the amount of people who would cover it.
No, I didn’t think it was going to be a hit record. I had my eye set on something else on the album. I was wet behind the ears. I didn’t know shit, but what was about to happen was just insane. And what kept happening, all the covers of that song, I never would’ve predicted that.
Is that something you appreciate, the covers and the samples?
Oh yeah. I get asked if I get tired of performing the song or hearing the song, but every time I perform it the audience makes it feel like the first time. So I’m appreciative of that and that it even happened to begin with. When that album was done and it slowly made its way up the charts, my dear friend Natalie Cole had a number one record with her debut album. She was number one on the Hot 100 and I was, like, number nine trying to get up into the top five. She called me one day and was embarking on her first tour. At this point I was looking for something to happen, regarding full-scale performing where I could get all over the country. This was perfect for me, the audience. It was a mix. Obviously, there were more Blacks than whites. It was a good mix, let’s say 6,000 Blacks [and] 2,000 whites, something like that. So, most of the people are coming out to see “soul brother” Bobby Caldwell. The first show was in Cleveland. When I came out on that stage to open for Natalie, you could hear a pin drop. It hadn’t even occurred to me, “What’s going to happen when they see I’m white?”
Did you know before the tour that people perceived you as Black?
Oh absolutely. Everything was pointing in that direction. Most of the radio personalities didn’t know. Some of them did.
That goes back to what I said earlier, though, that once you prove yourself they’ll accept you.
Yeah, and I think you said earlier, Black audiences are loyal to the core. They’re not going to, like, unfriend you.
.
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