Heather Headley

“If The Valley Isn't Deep You Don't Know How Amazing The Mountain Is!”

Let's Play had the esteemed pleasure of being at Chicago Shakespeare Theater Gala to honor the Spirit of Shakespeare Award Civic Honorees, Marilynn and Carl Toma and Spirit of Shakespeare Award Artistic Honoree, the incredibly talented John Lithgow. However, before the fun began, we had the honor of interviewing Tony and Grammy Award-winner Heather Headley.


Heather Headley (born October 5, 1974) is a Trinidadian-American singer, R & B, Soul, and Gospel songwriter, record producer, and actress since 1997. She lived in Fort Wayne Indiana, and attended Northrop High School, and was a member of the choir and starred as Fanny Brice in the school's production of Funny Girl. After graduating from Northrop High School, Headley attended Northwestern University to study communications and musical theatre until the last day of her junior year, when she decided to become a part of the musical Ragtime. Heather has won a Tony Award, a Grammy Award, and a Drama Desk Award, and nominated for a host of other acting and music accolades.

In Conversation With Heather Headley

LP: Thank you for this amazing opportunity. Tell us about your journey from Trinidad to Indiana to Northwestern University?

HH: Sure! I'm excited to meet with you. Yes, so I came to the United States from Trinidad the week of my 15th birthday, and we moved to Fort Wayne, Indiana. From there I went to Northwestern University, so the United States is more like my home now because I spent more of my life here.

LP: Fort Wayne, Indiana is not considered a destination place to live, so how did your family decide on coming to the land of the Hoosier?

HH: Well it was my father, (Heather laughs), it was his fault, and now I'm grateful for it. He was a pastor, and God worked it out that a church (McKee Street Church of God) offered him a job as a pastor near Fort Wayne, Indiana. They found out about my father in Trinidad through another pastor here, and they asked us to move to Indiana so that he could be their Pastor.

LP: How did the uprooting experience affect you?

HH: Well, for me being so young and knowing nothing about the United States, I didn't see how this was going to work out but I look back on it now, it was truly in God's hands the whole way. So to add to your first question, that's when Northwestern happened. At the time, I was three years out of Trinidad and didn't know about college and don't understand how college worked, but I had great teachers and guidance counselors. My family wanted to find a Big Ten college for me to attend; however, I wanted to be close to home and Northwestern University was chosen; which was also God working in my life.

LP: You were a young lady, almost 15 years old and had to transition from Trinidad to the United States. Talk to a young lady and help her with being able to make the transition in her life?

HH: Well, that transition was very tough for me, coming from Trinidad, from an Island to the land of everything, America. I was coming from the hot sun to the freezing-cold in October. From leaving my school and friends and dealing with the feeling of being fourteen and saying, I like him, I think he's cute to a whole new world, a new culture, and different people. My culture in Trinidad is entirely different; so I think you get sad. You get lonely, and you don't know anybody, and you have a very deep accent, and you don't know how to explain it to anyone, and I eat differently, but I do believe we can make it through transitions. My mother never said you couldn't do this. I do think that we sometimes instill things in children that you can't do it, but you can; you can make it through the transitions. 

I was looking at the movie Amistad, one day and found myself on my couch crying because, at a point in the movie, I figured out that there was some man, some woman who experienced that transition and made it. Many weren't able to make it, but two people of my kind were strong enough to make the worst transition of life. We are all from some amazing stock, and you are strong enough to make the transition.

Just remember, if the valley isn't deep you don't know how amazing the mountain is!  

LP: So, let's talk a little about your singing and acting career. We heard that after winning a Tony Award for Best Actress in a Musical performance as Aida in Aida, you took a short break from your career. Tell our readers why?

2018-06-09-21-02-35-108-1HH: Well, I have been married for 15 years and looking forward to celebrating 24 years like you too. I had two sons during that time, John David and Jordan Chase and every day they remind me that I'm not that cool, but they are truly a blessing to me.   

LP: Heather, you are just a phenomenal woman. You won a Tony, a Grammy and a Drama Desk Award (recognize excellence). What do winning these awards mean to you? 

HH: The awards are a blessing but they are not in places where I can see them, and I try every day to live my life for what it is now, but sometimes I do go into the room and say okay, I'm still okay, they still love me just for encouragement.

To me, it's not one of those things that I remember or reflect on all the time because I think every day I still want to work hard and didn't have that thought like I’m a Tony Award winner or I'm a Grammy winner so I can relax. It's more like the opposite effect. I feel like since I am a Tony and Grammy winner I have to work harder. There is so much more expectation.

LP: Heather, you did an excellent performance in the role of Shug, in The Color People in which you won the Tony Award for Best Actress; but how did your father, the Pastor feel about that role?

HH: Well, before I considered during the role, I called my Father who is my pastor and spoke with him and a lot of people close to me about the part. Then my husband and I went to see the show, and I will be honest with you, I went to see it with the thought of not doing it. I didn't want to replace anyone, so I actually said I'll buy my plane tickets because I didn't expect to do it and didn’t want them to pay for the tickets and invest in me, and then I say no thank you. However, during the intermission, I looked back at my husband, the big football player and he was crying, and he told me; you are going to do this play. I was like, whoa, what a minute, I didn’t agree to that. I was still contemplating, however, he said, we are going to clear the schedule and do whatever it takes but by the end of the show I was like, okay yes, I will do it because it was such a spiritual experience!

I believe that The Color Purple is so spiritual and provides such a great testimony of redemption and people lifting each other up and showing them God. It was such an honor and a beautiful experience to be a part of that play. The play is coming to Chicago soon, and at the end, they say amen and the entire audience becomes a congregation and says Amen. It’s truly a beautiful and spiritual experience.  

 LP: "He Is," and "I Wish I Wasn't" were two amazing songs and came to be every woman's song. Tell us what inspired those songs?

HH: Well I don’t believe our men, even today don't get the credit they deserve. Everybody beats them up, but I have a great man, and I think "He is," and I love him for being "He is;” so when you have a good man, we should lift them up. I believe it takes a strong woman to place her man on her shoulder and encourage him; so when I did “He is,” I called it a Hymn to Him.

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LP: Speaking of “He is,” you are raising two young men. Talk to us about that?

HH: Yes, I'm raising two sons and preparing them for what comes with living in our society. I want them to be amazing men! I remember sitting in a car with a girl, a friend a few years ago and she was balling (crying) about how this guy had treated her. I remember when she got out the car, and I said to my husband my sons will never have a girl speak of him like that. She can break up with him, he can break up with her, but he will never treat her like that. I want to raise them with respect.

LP: There you have it our interview with unconquerable Heather Headley!

To learn more about Heather Headley to go: http://www.heatherheadley.com/

Twitter: https://twitter.com/heatherheadley

Facebook: https://www.facebook.com/HeatherHeadley/

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