Heather Headley: written in the stars

Trinidadian-American star Heather Headley talks to Caroline Taylor about her Trinidad childhood, a new album, Whitney Houston, and The Bodyguard on the West End

Meet Trinidad-born sensation, Heather Headley

It took a while, but we finally caught up with Heather Headley for a proper interview in late January 2012, just a few weeks before Whitney Houston’s passing. We talked about her memories of and ties to her homeland, Trinidad; preparations for her next album; and taking on the role of Rachel Marron in the West End premiere of The Bodyguard musical that December.

Since then, Headley has gone on to release one more album (Broadway My Way); has had two more children (a boy, Jordan Chase born in 2014; and a girl, Eliana, born in 2019); did a limit run as Shug Avery in the acclaimed revival of The Color Purple on Broadway; and has pivoted to roles in television and film, recurring in She’s Gotta Have It on Netflix and NBC’s Chicago Med. She is one of the three leads in Sweet Magnolias, which premiered on Netflix in May 2020; and she will also play gospel star Clara Ward in the Aretha Franklin biopic Respect (scheduled for release on Christmas Day 2020). EGOT status — those who have won an Emmy, Grammy, Oscar, and Tony — beckons…?

It was never clearer what was “written in the stars”, or that — in Heather’s case — it is particularly true that “every story is a love story”. Her easy, down-to-earth vibe and quick wit make can make you feel like you’ve been pitching marbles together since school days, as more than one Trini reporter has commented. The laughs started early, so we give you pretty much the whole phone interview, right from the beginning.

Caroline Taylor: Hello, may I speak to Heather Headley please?

Heather Headley: [laughing] Speaking.

CT: [laughing] That’s the best reply I’ve ever gotten. How are you?

HH: [laughing] I’m good… You know, you talk to everybody and everybody’s American all day, then all of a sudden they’re like, ‘Remember you have that interview today’ and I’m like, yeah yeah yeah, and then I hear [imitating CT], ‘Hello, may I speak to Heather Headley please’, and right away, I know exactly who it is! I love it. How you doing?

CT: I’m all right. How are you? I know you’ve been sick the last couple weeks.

HH: Yeah, my son and I have been trading coughs. You know, because he refuses to stop kissing me. And I try, sometimes it’s awful, because sometimes I’m even giving him my cheek, and I’m like ‘here, here’ and he’s like ‘no!’ And he pulls my face… And, you know, we’re cooped up. And right now, I’m watching – and it’s beautiful – but I’m watching six inches of snow land on the driveway. But we’re heading south tomorrow, and that’ll make things better. We’ll breathe better; we’ll be out of the house… Everybody will just get better. I feel OK, a little cooped up, but I feel OK.

CT: I see you were asking your fans what to pack on your trip…

HH: Yeah, I know…and they’re totally not giving me anything today. But I am a bad packer, [my husband] Brian [Musso] always says. I am learning now how to just pack better. Because with all due respect, and I don’t like to generalise, but some of us Trinidadians are not great packers. Now listen to me, we know how to pack some food! We know how to wrap things up with masking tape and foil and get it here. My aunts have sent so much food the last few weeks for us… But you always see us: ‘Ah need a white pair of shoes, and den a black pair of shoes, and ah need a grey pair of shoes, and ah goin to de States so ah need meh long Johns’… And so I’m not good! My husband can pack in a plastic bag. And me, I need all my face stuff, and all my dis, and… I’m trying to be better so I can kind of race through the airport and not have the drama of all the packing. So it’s interesting to see what people say, and when you think about it, what I need. Like I said today, everything is purchasable, but there’s certain things that I’m like, this has to go.

CT: The great thing is for entertainment you can pack pretty much everything you need on to your iPad.

HH: Exactly, and that’s what I thought of. So if I’m stuck on the desert island, just give me my iPad. It’s got my games, got my books, I can reach out to people and say, come save me…

CT: [laughing] Yeah, if you got some Wi-Fi and 3G, yeah…

HH: Yeah, because if I’m stuck on a remote island, of course they have Wi-Fi…

CT: So you really read all the comments on your Facebook page and Twitter account and all of that?

HH: I do. I try to get through it. Number one I like to see what people think and want, and number two we have an administrator to make sure people aren’t saying anything offensive. Not necessarily to me, but I just don’t want any off-colour anything…

CT: Yeah, safeguarding the community kind of thing…

HH: Yeah, exactly, to safeguard the community… But I do read it. People have such sweet things to say, and such distinctive things that you really wanna think about. And yeah, sometimes I race through it, but people say such sweet things… You know, people talk about their babies and open your eyes to other things, and you’re like, yeah, you’re right. You know what I mean?

CT: Your posts and blogs are always fantastic and sometimes really uplifting for the people that come on and read as well.

HH: Aw, you’re kind… But I get up in the morning and I think, OK, what are we going to say, because I don’t really have time to do anything else during the day. So you’re gonna get it at 6am, because by the time the Commander General [two-year-old son John David] wakes up, I have no time… So it’s great to go through, and I really try to see what everybody’s saying.

Fan questions for Heather

CT: I asked a few people on our Caribbean Beat fan page if there is one thing they could ask you, what would it be? One that I love is: what other genres of music do you think you’ll explore next? I love that you don’t want to be pigeonholed as an artist, so what do you think is next on the horizon for you?

HH: Oh gosh… I think what’s scary about that is that the only thing left is like rap – gangsta rap – and country… [laughing]

CT: [laughing] Well, that actually ties in perfectly with our next question – will we ever see Heather Headley in Soca Monarch?

HH: In Soca Mon…! Oh gosh, no. And you know, on Twitter, I follow like Bunji Garlin and some other people and the things that go on in Trinidad… And people ask me would I do Soca Monarch – no! No! No! I am not gifted in that way. No, no. If you can’t cook that kind of food, stay out of it – bye! Now in my bathroom, heck yeah I try. In my bathroom I can still sing a good kaiso to myself, but never public. Never public. Ever.

You know, when I did that show in Trinidad the other day, we did “Hammer”, and I was very scared about it, terribly frightened. That was the song that maybe scared me the most. Because I said I wanted to do it, but I’m not going to do it Caribbean. Because to some extent, “The Hammer” is like the other national anthem of Trinidad, you know what I mean? Everybody knows it, and I thought one of two things is going to happen: they’re gonna be OK with me doing it, or these people are going to rise up in a mighty force and carry me outta here, with this dress on, to the airport. They may kill me before I get there.

I think because I grew up with it, respecting that music and understanding what it did to the island…I’ve learned from the performances of those people that I grew up with that I’ve looked at – the David Rudders, the Machel Montanos, who I remember singing [singing] ‘Dey say ah too young to soca, oye aye oye, aye aye aye…’ Just seeing their performances and seeing how they can make a crowd go crazy with simple songs, and yet songs about politics… I learned from those performances, but because I have this respect, interest and love for it, I won’t sing it. I don’t think I’m capable of singing calypso or being in Soca Monarch… No! [laughing] I am not capable. No, I can’t. I am not that good. Not at all.

CT: Are there any local artists that you might still like to do a collaboration with, even if it’s not in the soca genre?

HH: I would love to do…it would be fun to do a kinda soca thing. Because when you listen to someone like David Rudder, there’s a beautiful voice, you know what I mean? So it’ll be fun to do something with a soca artist. I think Destra’s got a great, great voice and it would be fun to just sit down at some point and figure it out.

CT: She actually sings some gospel and R&B as well…

HH: Yes, she does, and I think that’s what I heard her do at one point, and it kind of twirled by head! But that’s the beauty with us on the island… And that’s what I try to explain to people, hence my whole pigeon hole problem. That I grew up listening to all these musical genres… Bollywood, Scoutin – or as we like to call it, Scruntin’For Talent…there would be everything sung. So you have these Destras of the world who can sing calypso, unlike me, and then can sing a Whitney Houston song and whatever else she wants to sing. It’s great, so I’m proud of all that.

CT: I think the last question we got from a fan was: have you remained a Georgian in your heart?

HH: [laughs] Oh yes… George’s was my second school, because I started at St. Vincent Girls’ Anglican School. But yes, yes, I am still a Georgian at heart! I still remember those little halls where I had my first little guy that I liked, so you’re looking across the classrooms there…I still think of that stage where Rochelle [Lewis] – who conducted the choir for me and arranged a bunch of the songs when I was in Trinidad – where we would just sit and work on music. So to some extent, it was the start of a musical playground for me, and I didn’t know it. My music teacher would send us to work on these songs for graduations and funerals and this church and that church, not knowing that that was the beginning of teaching us how to arrange and sing, and do more… I mean, I sang before, but the arranging of it, sitting there and working through music… I always tell people that at that time – at that time – our meeting room was where we had assembly every day, was where we had graduation, sometimes where we had gym – it was all things. It was this big room to me, and the stage was so big… And in my mind, it still is this big stage, you know what I mean? It was the first place that I sang for like 700 people, singing the National Anthem or something. Yeah…

CT: How do you remember your time growing up in Trinidad, and the kind of mentors and idols that you had when you were growing up?

HH: I now remember it fondly… At the time when you’re growing up, it’s like, when are we gonna get to the States already… And now I look back, and I wouldn’t trade it for the world. I think it was the greatest growth process ever. It taught me so much.

I wanted to be my fifth standard teacher Miss Des Vignes who taught me math and called us uncouth. [Imitating] ‘You uncouth children!’ So there I was at 11 calling everyone uncouth! She said it with such grace, I almost wanted to be uncouth! Just seeing her walk into the room – like she had a bucket of water on her head, the way she would glide into the room – and I wanted to be her! And when I was in Standard 5, she found out I could sing – despite me trying not to let anyone find out. She was the scariest teacher ever, but I loved her, and she helped me through Common Entrance. So besides all the other women, there was one that taught me how to be a woman.

And I didn’t know it at the time, but those people in our church were really into the arts. There’s one guy – David Williams, who’s now a teacher. In our church he was just an artist – he would do drama, and art. And at the time, you just think that’s how people grow up, not knowing this was the first set of drama lessons I was getting… It was there in that church that I learned how to sing. So they were mentors, they were mentoring and they didn’t know it. I was being mentored and I didn’t know it… But they were all in that little church in Barataria.

Then you looked beyond it and there were these women on television, whether it was Janelle Commissiong or Giselle La Ronde… The other day I met her and I was still in complete awe. This beautiful, gorgeous woman, and remembering watching television, and her in that black dress [winning Miss World]… I’m like, Oh my God, it’s you – Giselle La Ronde! And now Wendy… But these are the women you saw on TV and were like, OK, I can be Miss Universe. I can be Miss World.

There were all these people around, these mentors that didn’t know it… And I say all that to say, a lot of these people were not necessarily on television. They weren’t people I couldn’t, in my head, aspire to be. I had these people around me, and I could look at Miss Des Vignes and say, I want to walk like her, or I want to be a teacher like her. And I think sometimes our kids, they see the Michael Jordans and Janet Jacksons on TV, and they don’t look at these people who are right here, who really do help influence your world as much as the others.

So Trinidad was great… I think of it fondly, I think of it respectfully, every memory is a sweet one, and as I said, I would not trade it for the world. It was an invaluable part of my life. It shaped me, and I love the fact that I know how to wash my underwear in the sink if I have to.

CT: [laughing] I think we all learn it, don’t we?

HH: Because that’s what Mummy said! [imitating] ‘Just because you have a washing machine doh mean you doh need to know how to wash it in de sink!’ She’d put me over the sink, and it’s just part of the deal to learn all that stuff. I couldn’t be happier.

Trinidad singer and actress Heather Headley

Trinidad singer and actress Heather Headley.

A star is born

CT: You mentioned your mum there, and there’s something in one of your blog posts that really struck me. You said that in the toughest seasons of your family’s life, your mother took the reigns and took you through that. How did that impact you? What was that about for you?

HH: Hm. You know… Coming to America, we had our issues when we came in, some tough times… Now I look back they look slightly easier… But as I think about it now, you have these seasons all the time, and there was always Mummy. She is the knees of our family. And on those days I don’t pray for myself, I know Mummy has. And Mummy is. And so there were tough times in college… I remember being in Ragtime and being like, I want to come home, why am I here… Mummy would pray me through, and be calling people and figuring out who she knew in Canada that could look after Heather. I got to Lion King and this was a completely different experience for me. I was on Broadway, and I was out of my realm! I had no idea what I was in for. And I would call her – poor Mummy, she didn’t know about Broadway, none of us did in our family – so poor Mummy is there trying to talk me through my first show on Broadway! There she was just asking God for wisdom, then she would talk me through Aida – I’ll give you a story about that.

She’s crazy, and she has her quirks when she wants to – of course, she’s a Trinidadian mom. And I don’t tell her enough, I don’t tell her as often as I should, but she’s a good mom, and she prays for us, and even from way back then… The other day when I went to Queen’s Hall, I could not stand on that stage without thinking of Mummy. The fact that while I was standing on that stage, Mummy was – I’m not going to cry! – Mummy was in the wings. You know what I mean? She had sat with me the entire time with me backstage, and she was in the wings. And I do believe, and I’m speaking to myself now even more as I’m speaking to you, that I think that’s where she’s always been. She’s always been in the wings, cheering us on. Even when I give her some trouble – [laughing] ‘Get out of the wings, you’re in my light!’ – you know, there she is in the wings. So she has helped us together during the toughest times, she held the reigns. I will say that we had some very strong women in my family, some terribly strong women, in our family who – when they’re called upon – they answer the call. Definitely.

Now the quick story. So, at the Tonys, Mummy’s sitting next to me because I took her as my date, and we had a very long conversation because she’d behaved what I considered to be very badly at the first awards show. The first awards show, they called my name when I won, Mummy jumps up, grabs my face, and puts it in her dress. All my friends were laughing at me because they said, ‘when they called your name, we never saw you – we saw your mother…jumping!’ So we get to the Tonys, and I’m like, [dramatically] ‘I have no idea what’s happening tonight. Most likely I won’t win. But if they call my name and you jump up, I will kill you myself, I will kill you myself!’ And this is happening at the Tonys. Poor woman. So halfway through the Tonys she comes over to me and she says, [imitating] ‘De Lord is putting it in meh spirit…Ah have a feelin you goin to win.’ And I’m like, ‘the Lord is not putting it in your spirit tonight. The Lord has better things to do! Leave me alone…bla bla bla.’ So then they announce the winner, and I’m thinking my mother’s womb must be by her ankles. I was nervous, I’m sure she was more nervous, and then they said my name…and that doll jumped off her feet – and jumped right back down. She jumped up like ‘thank-you Jesus!’ – then, ‘oops, I’m gon get killed!’ – and jumped right back down in her seat. I told her, ‘if you make a sound I will kill you! And I’ll go to jail because they’ll have it on tape.’ [laughs] But she’s a good egg. [more laughs]

CT: That is fantastic! [still recovering] OK, so how long before you moved to the States did you know that move was imminent?

HH: You know, my parents were talking like they were gonna do a move at some point, maybe on the island or to another island. It was very, very quick. We got to the States October 12th. I believe it started maybe nine months, 10 months before, because [my parents Eric and Hannah Headley] had gone to visit, gone to meet with the church during the winter before, but I don’t believe it was Christmas so I think it all started and ended in about nine months… We had to get visas for the whole family, the mayor in Fort Wayne [Indiana] got involved – it was a lot of work. But I didn’t have long… I remember telling everyone at George’s that I was leaving and then it was crazy. Which was maybe good for me.

CT: How did you make the choice to go to Northwestern, and then to withdraw and go in to Ragtime?

HH: By the time I went to Northwestern, we had only been here [in the US] for three years, so I was making a choice about college within two years of us being here. For us in Trinidad, I didn’t know what that whole college thing was. We had UWI [University of the West indies], but it’s a different feel, especially at the time. It was a big deal if you went to UWI. In fact I didn’t understand the fact that you could go to college close to home, but if you really went to college, you went to college far away from home. So we started looking at schools, and I was kinda nervous still about just America…

So again, God has sent me some great teachers in my life, and some great counsellors at high school, an amazing principle, who sat me down and said you can get scholarships, grants, you know, anything, and said they thought I should look further than just Indiana. And I say this very, very proudly – because of Trinidad, darling, I was pushed ahead in everything. I was in calculus in freshman year. So I was like this all AP [Advanced Placement] black girl that was way too smart. And all I knew is that this kid in the year ahead of me, Loni Davis, was going to be a doctor, and he was like the smartest black guy ever – and the cutest one, ever – and Loni Davis was looking at Cornell University and Northwestern University. So I thought, right, Cornell is too far, because I heard that’s in New York somewhere – somewhere beyond the seas – so this Northwestern thing, let’s look at it… Found out it was Big 10, it was four hours from home, had the best reputation ever, it was close to Chicago – because I wanted to try this music thing – and that’s how it started.

As far as leaving, that was a very tough decision. I was working professionally from sophomore year, with the help of teachers again. So my junior year, I got two offers that morning. I had one offer to be in Chicago and do a show in Chicago. And the other one was to do this audition for a show called Ragtime. So my agent said to me, ‘Just go do the audition, we just need them to see you, to know you exist. They’re not going to hire you, you’re too young, it’s in Canada – they’re not going to hire you.’ So I’m like, OK fine. And I wasn’t going to go. It was the last day of school, and I was invited by the football players – husband included – to go to dinner with them and my girlfriend. And I’m like, I can’t go to this audition – I gotta go get ready! And I go to the audition, remember very distinctly that they were talking while I was singing, which angers me. It angers me. So I kinda sang, and then I’m getting my book and they’re like, ‘Whoa whoa whoa! Hold on, where you going?’ And I’m like, ‘I’m getting outta here.’ And they’re like, ‘No no, we’re trying to figure out how to get you out of school, and you need to come back for the dance call…’ And I’m like, ‘Dance call, there’s a dance call?’ And they’re like, ‘The dance call, at five o’clock.’ And needless to say, the normal, amazing, in-their-right-mind person would be like, ‘Oh yes, I’m back here at five.’ Me, I’m like, ‘The football players asked me to go out with them, and I gotta pack up my room, and…’ [laughter] And they’re looking at me like, ‘Girl, what is wrong wit’ you?!’ But it all worked out, and that’s how that came up.

But, again, that is just a God thing because I do believe that God led us to Fort Wayne, He led me to Northwestern – for many reasons. Northwestern led me to Ragtime. Northwestern was leading me to my husband, so, I’m very happy about that.

CT: So you have the Ragtime, Lion King, and Aida experiences – and I was fourth row centre for Aida, which was amazing – you win a Tony, then you essentially withdraw from theatre for a while. What was that about?

HH: Oh gosh… Lion King and Aida was just…again, my family, my nucleus, did not know anything about Broadway. In my head, I wanted to be Whitney Houston. And so, I never knew about Broadway. So I think there are so many times that God just drops certain things in your life, and you’re not even looking in that direction, you know what I mean? You’re travelling down your little road and then He calls you and He’s like, ‘Look over here – come on, come on…’ And that road for me was Broadway. And I stood there and I’m like, whoa! I can sing dance and act all at one time? This is the best thing that ever happened. Tough – I’m not going to lie to you. Besides motherhood, that was one of the toughest things I did, it was a lot of work. And then the emotional weight of Aida, it was tough.

CT: I actually thought something had happened to you because of how emotionally raw you were, it was amazing.

HH: You know, not to digress, but I was so happy during that show because every time I would get to cry, like four times. So I would cry! I would cry about stuff in my life, I would cry about things… And I was so happy because I was like, people just need to cry! Get it out! So I would let myself cry. I would think of things, and just be in the moment, looking at Adam [Pascall] and he’s looking at me pitifully like, ‘We’re gonna die…’ And even sometimes just thinking of the journeys…you know, you can think of anything that would make me well up in tears. Like, 10 years ago I was in Trinidad walking bare foot across the street to Miss Philips’ house to get sugar, not thinking that 10 years later I would be standing on this stage playing Aida in Aida – with a Tony. OK, let’s cry. [laughs] Let’s have a good cry about that. So it was emotionally cathartic. I was just happy. And I could let everything out, and I was just happy and in a good place emotionally… I mean there was other stuff, I wasn’t perfect, other stuff would happen, but as far as the crying went I was good. So I had this thing, because I always thought at some point I’d love to record an album – that’s what I always thought. Not thinking Broadway was going to be this great, amazing experience for me, which was just the best, and God blessed me with something that I could not have written, because I didn’t know it.

CT: “Written in the stars”.

HH: Written in the stars, you’re so right! It’s like I always tell people, if you’re living on ground beef – which is fine – but then somebody says, ‘Did you try…the sirloin?’ And you’re like, ‘I did not![laughing] And I like that too! So that happened. And another God moment, people started coming in to the show, and then hearing that I wanted to do an album, and I had maybe two or three companies come to me, and then RCA came and said if I ever wanted to do an album, they’d love to do one with me. And I just thought it was the right time. I didn’t have another show lined up. This was the right time. And so we started working on it – while I was still in the show, which I think now was complete madness – but I recorded most of This is Who I Am while I was doing the show. I would sing 12–6pm, head to the theatre for 6pm, sing 8–11pm, and then sometimes our guy would pick me up to go back to the studio at night. It was madness. Now that I think about it, again, what were you thinking? So, it was tough but it was fine in the end. But going to that other side of it, the R&B side of it, I learned a lot with the album, learned a lot about the music business, liked it and hated it all at the same time, and just had a great experience.

Broadway also gave me a work ethic. On Broadway, we have eight shows to do a week. At that time, I never questioned whether I would do all eight or not, I did all eight. And if you’re late, you’re docked. So when I would tell people, I’m going to be at the studio at 6:30…get to the studio at 6:25, you know what I’m saying? So it was just the work ethic of singing sick…you don’t even know some of the things we sing through. I had dressers with buckets backstage because I was so sick… You come on, come off and whatever… So the discipline of it is second to none. They were all just preparation. And I had a great time with the album too.

Heather Headley Comes Home

CT: I remember reading that you were reluctant about – this is before Tobago Jazz – performing in Trinidad or Tobago because you wanted it to be just right. So your two big performances here have been Tobago Jazz and that great concert last month [December 2011]. What was it like for you to come back and perform in your home country?

HH: Tobago Jazz was nerve-wracking, but then again it wasn’t just me. I was surrounded by Diana Ross, and Mary J Blige, and, you know, that’s good! [laughs] Because, you know, you’re like, I know I just messed up – but look who’s here! [more laughs] Mary J! And Gladys Knight! I wanted it to be perfect so I was coming back there with Ricky Minor and the band, and we wanted it to be great and had a great time with that… But I hadn’t even gone to Trinidad.

So when this one came up, and they spoke to us, I believe it was a year. The first time we spoke with BG, there was snow on the ground and I was in a snowstorm or something. So I said yes, and at the time Wendell Constantine was going through what his vision was. And I thought, OK, sounds great. But we’ll see…thinking in a year this thing will still be knocking on our door. But I will tell you, it was the perfect way. I could not have asked for more. I mean, now I have problems with it because I think, I should have done more, I should have done this, I should have done that, but I loved working with BG, Derek Hudson and his wife Gillian, Wendell Constantine – who gets everything he needs to get done, done. I joked about him on stage, but it’s so Wendell. He’s got everything under control. And they were so sweet to us and so great to us and treated the team so well. You know, they really wanted it to be like this Home concert. So for me, I was just honoured to be there. But they were like, no, the daughter has come home, the daughter is here.

So they worked to make sure the theatre was right, that the lighting was right – and she was amazing! And all we did was talk over the phone. But everyone was supposed to be the top of what they did in Trinidad. You can’t ask for better. And I shouldn’t say ‘in Trinidad’ – just top of who they are! You know what I mean? These are people who would compete with anybody in the world. The lighting was amazing, everything moving, the crew… I was so proud of my little island, so proud just because of the talent. So to come back for that was perfect. I was gonna sing for murder. I told the band, I want you to leave everything on the stage tonight. When you leave here tonight, your liver must be following you out the door. OK, have a good night, no pressure! [laughs] My only regret was that we couldn’t go for longer… I wanted to listen! All so talented. The kids, the kids, the kids! I’m gonna start something there for them because they worked so hard, and Rochelle… it was amazing. So my only regret was everybody couldn’t do, like, three songs. So it was definitely the greatest highlight of my year, and it will always be in my heart. Always, always, always. Like your first love? I will always remember it. Always.

CT: I’m so glad you mentioned the kids and wanting to start something for them, because I realise that changing children’s lives is a really big thing for you, and I wanted to know a bit more about how you’re working in that area now.

HH: We’re part of a school here. It’s a scholarship school for inner city kids, and I love that. There’s something to be said for changing a child’s perception of who they are and who they can be. Sometimes you just need to change their perception and show them you can see further than this. And I’m not in the whole thing about, ‘I have to leave Trinidad’ – because Trinidad is showing the world that we have international talent. Anya, Wendy… You can grow and groom there. I just feel like somebody reached out to me, as we mentioned before I had these amazing teachers in my life, both in Trinidad and in the United States who led me on. And I think when I was down there, just looking in their eyes, I think I saw something in me in their eyes that I had not seen before. And I think what that was is them looking at me and saying, ‘You did it!’ For me, it’s just been my life. But they’re looking at me like, ‘Yeah, we can do this too!’

So, right. How do we make you realise all that, and get you ready? I got ready through high school, really – God moved things in different ways. So, maybe we can’t do it this year, but we’re starting to look at it, and talk to people, and just starting something for the kids and high schoolers there. And I really would like to get involved even more so with them. And they just plucked my heart. Rochelle would send me emails, Rochelle would Skype me and tell me how crazy it was, their dedication, how much they wanted to be in this choir, how much they wanted to be perfect. I mean, they were shaking backstage. And for me, I was like, let’s go sing and have fun! One girl was like, [imitating] ‘I am more nervous dan when I sit CXC!’ And I was like, what? You need a life! [laughing] But it didn’t hit me until I got there, but for them NAPA is Carnegie Hall. Their level of dedication – I was overwhelmed by it, by them. It was a great, great time. So hopefully we’ll get things started.

The Bodyguard & Plans for 2012

CT: This year is choc-a-bloc. So The Bodyguard [on London’s West End] is confirmed for later this year?

HH: It is confirmed! They have a theatre [the Adelphi]. I’ve been approving housing. They’ve sent me the script. It’s happening! So yeah, we start rehearsals September 10th. I’m not playing Whitney Houston, but I get to live vicariously through her music and be Whitney for maybe a year.

CT: When is it set to open?

HH: First previews are in November [6th], so it’s going to kick my tushie. And the decision was not mine but Brian’s. Once again, here it is that I have to say that he believes in me sometimes more than I believe in myself. I was like, it’s London, I’m going to have to take your child, you’re going to have to fly every week, and he was just like: ‘You’re going, you can do it.’

CT: And how about the Broadway CD?

HH: My aim is to have something recorded March/April and go from there… It’s all coming full circle. It’s going to be fun and very difficult now that I’m a mommy and a wife, and I’m older. So it’s scary doing the stage stuff, because again, it’s a different kind of discipline. But I’m started to get excited about it, it’s going to be a big adventure, and I’m ready to just jump into it and get going again. [Update: the album, The Only One in the World, was released in September, 2012]

CT: You still going for the Grammy-Tony-Oscar trifecta?

HH: Oh gosh, it would be nice… But maybe I’ve set my sights too high…

CT: You’ve already got two!

HH: [laughs] The other day I was thinking, come on, I’ve got to get this Oscar thing, and the Emmy… And someone was saying, ‘You know, you’ve got till you’re like 85, 86’…and then maybe they’ll just give me the Lifetime Achievement Award and I can just keel over and die like, I got it!

CT: [laughing] Clutching all the trophies on your deathbed!

HH: I know, I know! If my son doesn’t destroy them by then. Needless to say, I never thought I’d have one of the trifecta, or two. The Grammy in my head I always thought, oh wouldn’t that be good. A Grammy! And you kinda thought if you got down the right road, that could be possible. The Tony, again, was beyond me and is beyond me. I still go in the room sometimes and go, that’s here, the Grammy’s here…they live in this house with me? So I’m honoured I even have one or two of the Trifecta. One more to go.

CT: Is your son taking to your singing more?

HH: He is being better about it, yes. This month, I think he may have read my blog and found out that he is hurting me. So he’s better, but he only wants me to sing, like, his train songs. So I have to sing, [singing] ‘Little engines, little engines’, and then he says [imitating] ‘Again?’ So I sing his train songs for him. And then this morning, I tweeted he’s in the house and he’s going, [imitating] ‘Eeeeee, aaaaaaah’ [laughing]. So I’m telling him, use your words! And it took me forever to figure out that he was warming up! This is what I sound like to him!

CT: Vocalising!

HH: I know! And he’s got a good little voice, he can sing…I mean, when he sings, we know what he’s singing when he sings it. I’ve been trying to teach him all my church songs from Trinidad. Like, those are the ones I teach him. So that’s been fun, kind of going back in to my head and remembering those. He’s a sweet boy. It’s quite the honour to be his mommy. He’s a good boy.

Special memories

CT: OK, we’re on the home stretch because I know you have to pack…

HH: No girl, I have to shovel! [laughs]

CT: [laughs] Any special meaning that a song from each of your albums has for you.

HH: Ooooh… That’s not easy. I was trying to go through this the other day. Maybe “He is” from the first one. “In my mind” from the second one. And from the third one, I’ll go with “John David’s Song: This is What I Wish for You”.

CT: Do you still keep a journal?

HH: It’s sitting by my bed… I don’t write it as much because of the Commander General. I wanted to keep it daily, but when he was born I figured out I couldn’t do that. I tried…and then it went into like one sentence. Like, ‘This morning I…’ Then it ended. [laughs] ‘Last night I…’ [more laughs] But I hope to again when he gets a little older. I think I will write him a journal…well he’s gonna have a scrapbook. So I’ll start again, maybe when we’re in London. But yeah, it sits by my bed. When the big things happen, like I’ll journal about Trinidad, certain things when I’m like, this is a big God moment I need to write it down…

CT: Obama inauguration.

HH: There are a few times in my life that I will remember certain things. Needless to say like I just explained to you, my first time in Trinidad singing at NAPA will always be stamped into my mind. And one thing that will be stamped in my mind is walking out there…I just watched it for the first time in a few years. I was sick like a dog. I had laryngitis…sick like a dog. My poor doctor had me high on steroids…everything. I went to this New Year’s Eve thing with some friends, and I remember sitting at this table and feeling this cold air on me and thinking, Oh God I’m going to be sick in the morning. I could feel it. So the next morning I get up and I kind of have this sore throat and I’m like, I knew it. And I remember I didn’t need to sing, I remember this well – I didn’t need to sing until like the 19th. And so I thought, I have two weeks to just wash this out. Because I sometimes think that when you’re sick, your body just needs to get it out. Let’s just do it the holistic way, and I had the time. So I thought let’s go to Florida and go hang out. So I’m down in Florida and obviously this was more than just a cold and sore throat.

So I’m washing it out and not talking, then my manager calls me and tells me they want me to be in the Obama inauguration. And I’m like, [imitating hoarse, raspy voice] ‘But I can’t sing…!’ And he’s like, ‘Oh you’re gonna learn how to sing. You are gonna sing! Figure it out!’ That was like the first time he yelled at me! [laughs] Long story short, I had laryngitis. So I get back and go and see my voice doctor in Chicago and am like, you gotta get me better. Right now. Or I’m firing you. [laughing] I mean, I wish that I was better…but I will never forget. I will never forget walking on that stage and looking from my side out. There are only a few people in the world – maybe a couple thousand – who have ever looked at that. And among them is Martin Luther King Jr, you know, who’s looked out and seen three quarters of a million people just lined up. And there I was singing for it! And I think when I’m like 90 years old sitting on my couch with the grandchildren, I’ll be like, [putting on her ‘granny’ voice] ‘Do you know where I was on the 19th of January 2009?’ And the kids are going to be like, ‘We wish she would die!’

CT: [laughing] They’ll probably be reciting the story verbatim with you!

HH: Yes! Exactly! [imitating] ‘You were on the steps of the Lincoln Memorial singing for 750,000 people and Obama…. When are you gonna die?’ [laughing] And I think I might be the only person who would ever say this, but it was bigger than Obama for me.

CT: Of course.

HH: Yes! It was about how I was looking at America at her finest. For my second home, America y’all are kinda cool. Look at this! I wanted to scream, ‘you’re the best!’ And I will say this too…I’m so happy and proud of America for having a black president, but it’s weird – Trinidad kinda got me ready for that, you know what I mean? I knew that could exist, you know what I’m saying? Because I grew up on an island where there was a black president. Why wouldn’t there be? So when he was elected, I was like, I know that this can happen because I come from a place where it happens! It was a great moment, and only after was I calm, and happy, and could breathe…I don’t think I took a breath for hours.

CT: By contrast, what do you think your disappointment has been?

HH: Oh goodness… I can’t even call it a disappointment. But I wish I had met Brian earlier. I wish I hadn’t played around…I mean, I didn’t date that many people, but kinda wish I had never even liked anybody else. But I think you have to like the idiots so that you can love the great guys. [laughs] And I wish I had met him in college and dated in college…it would have been fun to date him. He was up the street being cool, you know, and not paying me any mind. And I remind him of that. [laughs] We didn’t know each other at all, but I wish that. And now that I have had John David and he’s such a great part, I wish I had more years to have another little him… Just him, nobody else! [laughs] I think that’s it! I think there are disappointments in your life, things you want to do, but when you look at it in the larger scheme of things, that’s not what God has planned at that time. And what God has planned has been great. And I feel we’ve followed his lead, and that’s better than anything else I could have done. So that would be it. Like I said before, I haven’t given my mom the ‘I love yous’ enough. And maybe that’s disappointing and I need to fix that. As I’ve grown older, I’ve also seen how cool my family in Trinidad is. The night they all came to hang out with me in Trinidad, I didn’t speak, could not speak, because I had the show the next day…I couldn’t be part of the group or make jokes, but I think it was good because all I had to do was sit back and watch and laugh. And just feel like, you guys are the best, the best, the best. So maybe I need to tell them more. But as far as regrets, as the song goes, I have but just a few…too few to mention. [laughing]

CT: What do you miss most about Trinidad?

HH: I hope this hasn’t changed, but I miss the community of the island. I think because of our heat we can be outside…I remember Brian laughing that he’d come to Carapichaima to meet my family, and my Uncle John was sitting on the stoop outside the house playing dominos, and we left and came back about eight hours later…and my Uncle John was sitting on the stoop playing dominos. [laughing] Brian’s like, ‘Has he moved?’ And I’m like, I don’t know…but why would he? [laughing] But it’s that community. I’m thinking in the time that he was there, maybe 20 people came up and played dominos and hung out. At Christmas time you go to people’s houses, and you eat and play parang. You know? It’s the community, the culture. The yelling out from the back yard, [imitating] ‘Yuh have some sugar ah could borrow?’ It’s that. Last night I made a very bad callaloo and it’s terribly bad…but I was eating it like it was the best thing ever. But it’s just the culture. I remember going in my grandpa’s back yard and helping pick dasheen bush and sugar cane and…the culture of it. You know? Just the village, the community…if you walk down the street and if you don’t say hello to Sister Alleyne, by the time you got home, she’d have called and said, [imitating] ‘Heather pass in front meh house and didn’t say hello!’

The community raises you. That’s how it was. I don’t know how it is now. Now that I’m older, I miss the things that people wouldn’t appreciate that much, you know? The simple things. Going ’round the Savannah and getting pholourie or doubles and a coconut. And calling that a date! My manager and I are driving around the Savannah and I’m like, you realise this is like date territory right here… Just the beauty of it and how we live and how we don’t live. I think that’s the stuff I love. As I walked and drove through Trinidad, everywhere I went there was this overwhelming love and pride that came over me like a river from everybody, and it was just sweet… We’re just good people. I know there are some bad apples that try to make it bad for everybody…but it’s a cool group of people. And I do miss the food. There’s nothing better than that. I think I got in trouble with some Jamaicans…I’m surprised they haven’t found me. Mm. Because my mouth ran a little bit and I said on somebody’s show that I wouldn’t eat a roti from Jamaicans in America, so…

CT: I got the worst run-belly from that, so I totally endorse that statement.

HH: Thank-you! Thank-you! That’s what I was trying to say. Y’all can do jerk chicken and acki and saltfish, but don’t touch this. I know! [laughing]

CT: I was just passing through a store [here in the US] the other day, and the title one of the food aisles was ‘Jamaican and West Indian’.

HH: No, no, no… No. We can’t have that. You need to burn that aisle down. Light it on fire. I’ll bail you out. Light it on fire.

CT: I’ma hold you to that! ‘Heather Headley said’…

HH: I know, I’m gonna get a call in a few hours, saying [imitating me] ‘Heather supposed to bail meh out!’ [laughing] Can’t you see it?

CT: [laughing] ‘She a singer, she ha’ two big awards yuh know!’

HH: [laughing] I know! ‘No, I do not know her…’ But then you’re like, ‘I have it on tape, she’s s’posed to bail me out!’ But no, the food I love. And my Auntie Brenda and all my aunts, who I do love, I know their way of saying they love us it to send food, and to cook. And so my mother leaves here with amazing suitcases – too many – and somehow comes back with all of them filled. And I’m like, how do you come back here with 200lbs of anything? What? And she opens that suitcase, and there’s this waft of air coming from there… And she has the special things they have to send for Brian. They have to send him pepper sauce, and callaloo and roti…all this stuff. I just love the food. I can’t have enough of it… I have always been like, ‘I am woman, hear me roar! I don’t need to be in the kitchen. And second, I will never learn how to make callaloo and pelau. What’s your problem? That’s not what I do!’ And he went to Trinidad the first time, and I remember him sitting there in the kitchen eating my aunt’s cooking, and he’s like, [imitating] ‘You know how to make this? You need to learn.’ So I got a Naparima Girls book for my wedding, and he loves Caribbean food so it’s been fun to cook that for him when I can. Needless to say it’s not as good as my aunt’s… My pelau looks a lot like a coocoo… But it’s so good!

For more on Heather, check out the cover story in the May/June issue (#115) of Caribbean Beat, Discover’s sister magazine.


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  1. Beautiful article. Heather has such a great spirit and just radiates pure joy.


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