The 10 Best Heather Headley Songs of All-Time

Heather Headley

Many know Heather Headley for playing ‘Helen Decatur’ in ‘Sweet Magnolias, a romantic show on Netflix. But they do not know that this American singer-songwriter, actress, and producer has an impressive success record. She’s one of the all-around personalities in the entertainment industry, admired for her outstanding performance on stage and on record. Born in Trinidad in 1974, this Broadway star has perfectly demonstrated her singing and acting talents for over 20 years. She is among the few artists who make a name for themselves with their first album. Her debut album ‘This is Who I Am’ earned her two Grammy award nominations. One for the Best New Artists that saw her win the Tony Award, and the other for the Best Female R&B Vocal Performance. Since then, she’s released several recordings, most of which have become a favorite to many, landing her more nominations and awards. Thanks to her good tone and ability to control and project her powerful voice in all her recordings. Let’s look at some of the best Heather Headley songs in history.

10. A Little While


Waking up and realizing that the words’ till death do us part were but a meaningless phrase can render you numb. Unsure of what to do, you’ll convince yourself that everything will be well. But this song will give you hope as you try to cope with the pain of divorce. It reminds you that God will see you through regardless of how hard the situation may seem. All you need is to pray and hope for the best, and within a short time, you’ll experience peace and happiness and have the strength to move on. That’s the message from this 6th single in Heather’s fourth album, ‘Only One in the World.’

9. I Didn’t Mean To


It’s beautiful to fall in love, marry and welcome your first little bundle of joy. But it becomes a different story when you walk into your house and find your spouse cheating on you. It can be a devastating and painful experience that will leave you with so many unanswered questions. However, your only option will be likely to walk away from the relationship and take your child with you. This single from Heather’s second album, ‘In My Mind,’ talks about infidelity- one of the main reasons for many family breakups. It cautions people to be faithful to their partners.

8. What’s Not Being Said


Why is it so hard for most people to keep their flame of love burning forever? It’s amazing how there’s so much love, care, and passion in the early stages of relationships, but people become strangers as years go by. All the sweet words become history, the promises to each other go unfulfilled, and the relationship starts falling apart. This 7th single from ‘In My Mind’ album is about a lady whose love story turns sour. Even though she can read between the lines, she still hopes to hear from her ex.

7. Always be your Girl


They say the truth hurts but being lied to hurts the most. However, most people in relationships choose to lie rather than tell the truth. They forget that the partner will come to learn about their dishonesty and hurt so much and maybe forever. They’ll also lose trust in them. This song teaches us the value of openness in a relationship. It talks of close friends (a lady and a man) who have been intimate. But the man starts seeing another girl and does not disclose it to his close friend, who later finds out. She feels lied to and wishes that the man could be honest about his feelings for her. The ballad is the 7th single from the singer’s first album, ‘This Is Who I AM.’

6. Jesus is Love


‘Jesus is Love’ is one of the greatest hits that showcase the singer’s faith in God. It is the fourth single from ‘Audience of One,’ her third album. It talks about the love Jesus has for his children and reminds us to trust in Him, love one another, and be thankful. The lyrics echo Christ’s promises to those who have faith in Him. Listen to this song, and you’ll have every reason to be grateful to God for the many blessing in your life. It’s a song that will keep your faith up.

5. Ain’t’ it Funny


We learn a lot from the twist and turns of life. That’s what makes the process and experiences of this journey fascinating. Imagine the person who broke your heart previously coming back desperately needing your help and love. The singer’s message in the lyrics reminds us of how unpredictable life can be. The song also cautions us to end our differences amicably. It is one of the songs featured in the Diary of a Mad Black Woman film.

4. He Is


Here is the first single from Heather’s debut album that earned her great fame. The song describes who a man is or should be in a relationship. Does your partner match what Heather has listed in this song? The undoer of the bad times, releaser of your pleasure, giver of love and joy, defender of your soul, to mention a few? This is an excellent song to play when you want to appreciate your life partner and remind them of what they should bring into the relationship.

3. Me Time


Some people are so insecure in their relationship that they don’t give their partner space. This can suffocate the person who wants some ‘me’ time. Does this look like your situation? This song can help relay the right message to your insecure partner. It is one of the singles in the ‘In My Mind’ album and yet another great love song from this talented artist. It peaked the fifth position at the Adult R&B Airplay

2. I wish I wasn’t


Falling in love is sweet but hurts deeply when the feelings are not mutual. You expect the person you’re in love with to reciprocate the same level of affection, but they don’t. They claim to love you, but their actions convey otherwise. This song talks about one-sided love, and it’s the second single from the singer’s debut album, ‘This is Who I Am.’ It was released in 2002, peaking at no. 1 on the Adult R&B Songs chart

1. In My Mind


This song is a cover from Shannon Sander’s first album. It was released in 2005 and is the lead single from Heather’s second album bearing the same title ‘In My Mind.’ It achieved moderate success on the Billboard Hot 100, raking position 25 and no. 2 on the Adult R&B Songs chart. It is worth listening to after a breakup. It’s a song that will help you move on even after discovering that your ex is in another relationship. It talks about letting go and wishing the other person well in their life and future relationship.

Final Thoughts

Most of these great hits magnify heartache. We cannot deny that they mirror what many people go through in relationships. Heather has used her lovely tone to tell the painful stories surrounding love and marriages. She also encourages the heartbroken to pray and make better choices to help them heal and move on. These songs are a good choice for anyone coping with divorce, infidelity, or breakup. For those in a beautiful relationship, there is a ballad on the list for you to celebrate your love.

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