Award-winning Canadian singer-songwriter Henry Lees transforms personal grief into a moving tribute to his late sisters on his poignant new single, “That Last Goodbye.”
Sometimes, there are no easy goodbyes, especially when they’re final. For Canadian singer-songwriter Henry Lees, losing three of his sisters in less than a year brought unimaginable heartbreak. Now, he’s turning those experiences into music with his deeply personal new single, “That Last Goodbye,” available now.
Created alongside Nova Scotia songwriter Joanna Butler and Ontario songwriter and producer Allister Bradley, the emotional release explores grief, remembrance, and the healing power of music.
Henry Lees That Last Goodbye – A Song of Grief and Healing
Between late 2022 and mid-2023, Lees lost his sisters Lawna, Laura, and Linda to forms of dementia, including early-onset Alzheimer’s disease and Primary Progressive Aphasia. All three were 70 or younger.
Having previously lost his youngest sister, Lila, to cancer in 2009 and both parents in 2003 and 2011, Lees found himself navigating another devastating chapter of loss.
“When my sisters died in such rapid succession, I felt like I had been totally cut adrift,” he recalls. “I had landed on a desert island by myself with nothing but the sound of the waves and the wind and my own thoughts.”
Although music had long been an important part of his life, Lees initially questioned whether he could confront something so deeply personal through songwriting.
“This is something I thought I would never have the courage to write about,” says Lees. “I thought it would be too painful and close to the bone but thanks to two wonderfully supportive and insightful collaborators, the time finally felt right to go there. I’m so grateful we did.”
The Story Behind Henry Lees’ “That Last Goodbye”
Two years after losing his sisters, Lees participated in a SongStudio songwriting workshop, where he collaborated with Nova Scotia songwriter Joanna Butler for the first time.
Despite never having worked together, the pair quickly discovered a shared understanding of grief, creating an environment where vulnerability could become the foundation of something meaningful.
“We didn’t know each other, yet we both understood the pain of losing someone,” Butler explains. “You could feel the wave of emotions in that virtual room, and our challenge was to capture them in a song.”
Butler, who has collaborated with Canadian artists including Meaghan Smith, Dave Gunning, Terra Spencer, and Bruce Guthro, helped Lees find the courage to explore emotions he had previously struggled to express.
“I felt comfortable in being open hearted and vulnerable with Joanna from the get-go,” Lees recalls, “and that was key to the birth of ‘That Last Goodbye’.”
Producer Allister Bradley, who was involved in managing the SongStudio workshop, immediately recognized the song’s emotional potential.
“They had very quickly built a song that caught my ear in such a beautifully longing way,” Bradley shares.
After creating a piano-based demo for the workshop, Bradley returned to produce the final recording.
His delicate piano arrangement supports Lees’ heartfelt vocals and Butler’s harmonies, allowing the instrumentation to communicate the emotional weight of the lyrics.
“I very much approached the instruments as a hidden opportunity to tell as much story as the lyrics,” Bradley explains. “I aimed to capture the song’s turmoil – the swirling confusion, the longing, the inescapable weight and the loneliness – in the instrumental track itself.”
For Lees, the result was deeply moving.
“Allister’s affinity for our song and its emotional theme is so evident in the instrumentation and production,” he says. “His piano melody on its own gave me the best goosebumps on first listen.”
Henry Lees’ “That Last Goodbye” Earns International Recognition
The emotional impact of “That Last Goodbye” has already received recognition.
The single was named a semi-finalist in the Folk/Singer-Songwriter category of the 2025 International Songwriting Competition, marking Lees’ twelfth honour from international music competitions since 2021.
“That kind of thumbs up from your peers is so validating and thrilling to receive,” Lees says. “It underscores that it was a good thing to create from this very personal place.”
The release follows his previous singles, “Into Your Orbit” and “Smoke,” which have collectively earned more than 10,000 streams and placements on Spotify’s Daylist and Mixes.
Both tracks have also received airplay on college and community radio stations across North America, the United Kingdom, Europe, and South America, along with recognition from the International Songwriting Competition and Unsigned Only Music Awards.
Henry Lees Hopes “That Last Goodbye” Helps Others Through Grief
While awards and streaming milestones are meaningful, Lees and Butler hope their collaboration will have an even greater impact on listeners navigating personal loss.
“I hope listeners feel an emotional release, knowing that others wrestle with the same feelings after losing someone,” Butler explains. “There’s something so freeing about hearing someone express what you haven’t been able to say.”
For Lees, the song is both a tribute to his sisters and an opportunity to connect with others experiencing grief.
“In honour of my sisters, I really hope ‘That Last Goodbye’ can connect with as many listeners as possible who may be going through seemingly insurmountable loss,” he shares. “It’s not a magic potion but music can definitely help us feel less alone.”
To learn more about dementia and support Alzheimer’s research, visit the Alzheimer Society of Canada.
Hi, Henry ! Good to see you again! Care to introduce yourself to the readers for those not familiar with your music?
Hi! Thank you for this opportunity. It’s always great to come back to Canadian Beats with new music and share the inspiration behind it. I’m a singer-songwriter and percussionist from Toronto, originally from B.C., who loves to let the songwriting muse lead the way to wherever it takes me. My recent releases have been pop-leaning but I’ve written and recorded songs that span folk, country, rhythm and blues and rock. I’m a big fan of collaborating with different writers and producers to see what we can conjure up.
You lost three sisters, Lawna, Laura and Linda, in less than a year, after already experiencing the deaths of your youngest sister and both parents. You’ve described feeling like you were stranded on a desert island after those losses. What was that period of your life like, and how did you begin finding your way through such overwhelming grief?
After losing three of my sisters within 8 months from late 2022 to summer 2023, I was alternating between an odd numbness, feeling waves of despair and the sobering realization that I was the only one left of my immediate family. That’s where the alone-on-a-desert-island feeling comes in. I have extended family and dear friends who are wonderfully supportive but there’s a seemingly unshakable sense of loneliness when you’re the last one left alive in your family – the family who raised you.
It can be easy to let that oppressive grief take over but, believing that your deceased loved ones would never want you to live in pain is a strong motivator to move through it. I don’t think grief ever totally abates. With time and intention, it hopefully softens as it mixes in with sweet memories.
In addition to the healing that love from other family and friends brings, music is such a powerful healer. Writing, recording, performing and the creation of a new piece of art is pure joy for me and definitely a potent medicine, especially when that beautiful human connection occurs when that song is shared and moves another listener.
You’ve said you never thought you’d have the courage to write about losing your sisters because the experience was simply too painful. What changed that made you feel ready to tell this story through music, and was there a particular moment during the songwriting process when you realized how much you needed to write it?
Lawna, Laura and Linda all passed away as a result of having forms of dementia including early onset Alzheimer’s. I was afraid that drawing inspiration from that long, deep period of grief from their initial diagnoses to their deaths would make me backslide into a dark place I had worked hard to climb out of. I had resigned myself to the fact that I just wouldn’t allow myself to ever go there musically. However, I believe that artists need to observe and explore the full spectrum of human experiences both internally and externally to grow, even those experiences that are uncomfortable and scary.
I’m still a little mystified as to why it happened when it did, but just prior to my first co-writing session with Joanna Butler two years after those sad goodbyes, I suddenly felt like it could be the right time to pull the lid off that box and take a good look. I was still apprehensive but I also fell back on the wonderful memories of my sisters encouraging my musical pursuits when they were alive. I felt like they still would be doing so if they were here and would want me to make something good from that grief.
You had never written with Joanna Butler before, yet you found yourself sharing some of your most personal experiences during your first songwriting session together. How did that immediate trust develop, and what did Joanna and producer Allister Bradley bring to “That Last Goodbye” that you might not have been able to express on your own?
Joanna is a warm, open-hearted person who obviously loves music and creating as much as I do so, I felt comfortable sharing those personal experiences with her in the intimate, one-on-one co-writing space. She is no stranger to loss and that created a connection and kinship from the get-go. Everyone has their own unique story – which is an observation that made it into the song.
For a place to start, Joanna suggested that I interview myself about my experiences with loss and grief and journal both my questions and responses. That was key to understanding and honing in on the song’s focus and message. Getting those deep thoughts out of my head and into a document unlocked a great creative flow and soothed my fear about expressing that grief in song. Joanna also helped shape the lyrics with me so that “That Last Goodbye” is both my story and a story that could connect with any type of deep personal loss.
Allister Bradley was a spot-on choice to produce the song. He had already collaborated with us to create a piano-based demo and blew us away with what he came up with. We are so thrilled with what he brought musically that takes a very sad subject and lifts it into a beautiful soundscape. I would have never thought that a pretty, lilting piano figure in 6/8 time would be such a perfect accompaniment for a song about bewilderment.
“That Last Goodbye” has now earned recognition from the International Songwriting Competition, but you’ve said your greatest hope is that it helps people experiencing loss feel less alone. How has sharing such a deeply personal song changed your own relationship with grief, and what would you want someone who has recently lost a loved one to hear in it?
For me, the worst part of grief is how isolating it can be, even though everyone experiences the loss of someone they love. At a time when we likely need the support of human connection the most, we can feel at our loneliest. Joanna and I hope “That Last Goodbye” can inspire listeners to hear their own stories in the song and feel connected to anyone and everyone who goes through similar times.
In the very short time since the song’s release, I’ve already heard from listeners who’ve been moved by it and relate it to their own grief journeys. This precious song has changed me to now know that creating it and not shying away from those dark emotions can actually bring you closer to the light of joy. I’ll always be grateful for that.
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