Single Premiere with Q&A: Jesse Lynn Madera Welcomes the Holidays with Retelling of Christmas Classic

Chris Epting
7 min readOct 22, 2020

Jesse Lynn Madera delivers a timely and exquisite cover of the classic tune “Have Yourself a Merry Little Christmas,” produced by and featuring Grammy Award-winning piano virtuoso Matt Rollings. Recorded live at Rollings’ home studio, Madera’s vocals and Rollings’ playing convey an enduring holiday standard in a stunningly intimate and alluring cover.

Have Yourself A Merry Little Christmas is arguably one of the most well-known songs in the Christmas archive. What drew you to this tune?

The holidays were always a big deal for my family. Life was not easy, but we had a fierce loyalty to Christmas joy, or I saw it that way. I’m not sure if it has something to do with my mom and I having the same birthday, maybe there are personality traits we share because of that. We were both born in what some astrologists refer to as “The Week of the Child.” Our ability to suspend disbelief and get lost in magic, even if it’s “magic” we know we created, is something I hope to pass on to my kids.

My husband was in the hospital last Christmas following a scary emergency surgery. It was the most terrifying moment of my life, not knowing for sure what was going to happen. We’d somewhat fortuitously decorated early, and I was so thankful that we did. I remember one exchange with my son as he was placing an ornament on a branch. He asked me if Santa was real. “What do you think?” I responded. He paused, and then said “I don’t know.” A few minutes later he was behind the tree, plugging and unplugging the lights, marveling at their beauty. I said “George, you see that it’s you making the lights go on and off? Remember this, because it is one of the most important things I’ll ever teach you. You create your own magic. The lights are not any less beautiful just because you know it’s you who is plugging them in.” That was my way of answering that question as gently and honestly as possible.

That year, with Hemky in the hospital, the mortal-made magic of the plastic lights in their dance with the mysterious miracle of electricity, the tree, the sentimental ornaments, the familiar songs, the presents for the kids, leaving out the cookies and carrots for Santa and his reindeer, were all medicine for our souls.This is a long answer to a specific question, I know. The point is, this is not going to be a ‘normal’ holiday season with this pandemic going on. There are also going to be a whole lot of people who are unhappy with the results of this contentious election. I chose this song to urge people to recommit, or commit for the first time, to stubborn optimism. It’s all we can do.

Choose to get lost, and in the process, found, in the glow of the lights. Make your grandma’s rolls. Decorate early. Love furiously. Be warriors for kindness, gratitude, and generosity. Forgive one another. This is what it means to hang a shining star upon the highest bough. The original lyrics to this song, as penned by Hugh Martin, were almost amusingly morose. Judy Garland was to perform it in “Meet Me in St. Louis,” and begged him to change the song to be more upbeat. The evolution of the lyrics is a metaphor in and of itself. Every moment of our lives, we have a choice to make. Will we be stubbornly sad? There’s always going to be fuel for that. Or could we be stubbornly hopeful? What’s the best use of our time here?

Can you tell us how your influences contributed to the style of this cover?

I strongly prefer the classic Christmas songs from my childhood. Bing Crosby comes to mind. I wanted to perform this in a way that was familiar yet authentic. I knew I would be able to bring a timely, modern, meaning to the performance, because the lyrics are so apropos to what we’re all living through right now on planet earth in the year 2020. I wasn’t too concerned about it sounding out of date for that reason. At the same time, this is far from the first Christmas through which people have muddled. So, while my interpretation performance-wise is very much of the now, the story carried by the song is timeless. The arrangement needed to feel timeless. There is comfort in remembering that both suffering and the relief of that suffering are forever, and that our ability to endure is in our DNA. People were muddling through Christmas when the song was written in 1943. They were before that, and still are today. Ain’t that comforting?

What (or who) brought you together with Grammy Award-winning composer and producer Matt Rollings to collaborate on this single?

Nobody alive today plays a standard better than Matt Rollings. Matt also happens to be a fellow sparkly-eyed, young-at-heart human, and a friend of mine. I’ve been wanting to work with him on something for years. We met through a mutual friend and talented multi-instrumentalist, Ben Graves, several years ago at the 101 Diner in Hollywood. He was the first person I thought of, and my first text.

Did Matt have an initial vision for how he wanted the song to sound? Tell us about the process of working together.

The stars happened to align in every way for this to happen. I knew I wanted our rendition to sound like something I would’ve heard spinning on my grandparents’ record player while eating fudge and guessing which presents were mine. That led me to Matt. He produced and won a well-deserved Grammy for Willie Nelson’s Summertime: Willie Nelson Sings Gershwin. His old soul musical sensibilities are beautifully in tune with songs from that era. We recorded live in his home studio. For the first couple takes, he was playing so damn beautifully that I got distracted! I was dragging the song, singing behind him instead of leading, and he had to gently ask me to take charge of my performance so that he could follow me. I probably turned bright red. I was like “Oh! Sorry, sorry, sorry!” I snapped out of it then and got the job done. In the end, we’re both enamored with what we did. After that warm up, I think we got it in three takes. We didn’t rehearse before the tracking day, so what you hear in the finished product, aside from the gorgeous string arrangement by Kristin Wilkinson, is truly a window into that particular day and time.

Last year you released a cover of “White Christmas,” do you plan to make this a yearly tradition? If so, any hints to what we can expect in the coming years?

Yes! I think so. I have a few ideas. Someone close suggested “I’ll Be Home for Christmas,” but we’ll really have to see what resonates with me next year. With “White Christmas” I’d just moved to Nashville after nearly ten years in Los Angeles, and was really excited to be closer to my home state of West Virginia. The frost in the air took me back to my grandparents’ tiny living room in Parkersburg, with the snow falling outside. That’s what I was thinking about when I tracked that at Willie Breeding’s studio in Nashville.

Speaking of traditions, what are some of your family’s Christmas traditions?

Every year on Christmas Eve my mom makes Beef Wellington with mushroom pate instead of liver. It’s a must! If I don’t have it, I feel like I’ve missed out. We try to buy ornaments to commemorate special things we’ve done throughout the year, so revisiting the ornaments while we’re decorating is always heartwarming. I play a ton of Christmas music, and have a special place in my heart for The Chipmunks’ Christmas music. We always leave milk and cookies for Santa, and carrots for his reindeer. Boy are they messy eaters, but at least they always leave a thank you note. We read Night Before Christmas before bed on Christmas Eve. Usual stuff I think!

I wasn’t raised with religion. Of course I knew the story of Mary, Joseph, the wise men, and Jesus, but for us Christmas was more about recommitting ourselves to hope and stubborn optimism. I understand that the holidays are really hard on some people, that they bring up bad memories, or they make people yearn for family they’ve lost. I have those feelings too, but I find a huge amount of comfort in carrying on traditions. It’s like an annual exercise in making the most of things. My grandma’s hot rolls, my favorite great-aunt’s pie, those things bring me comfort.

Things will look different for many families this Christmas. Any words of hope and encouragement you would like to share?

At the risk of repeating myself, or hammering too hard on this, hope is a choice. I’ve dealt with my share of pain and depression. It only makes me more determined to find whatever joy I can and fan that flame. I encourage everyone to amp up the cheer this year. Turn it up to eleven. Quantum scientists tell us about energy, and what it does, and what it looks like. There are special cameras that can even see our feelings. Whether we realize it or not, we are affected by the energies on the earth. Fight for harmony by being in harmony. Fight injustice by giving those closest to you the benefit of the doubt and by knowing that you are always capable of growth, no matter your age. As you’re plugging in the lights, do it with awareness. Know it’s a metaphor for your choices all year long. We can change the world by being the best versions of ourselves, and inspiring others with our generosity of spirit.

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Chris Epting

Award-winning journalist, author of 30 books including James Dean Died Here, Roadside Baseball; lover of music, travel, history, etc.