From Bedroom to Billboard: The Unlikely Alliance of Frank Watkinson and Break Out The Crazy
How an Indie-Folk Legend and a Modern Duo Reshape the Music Landscape Through Collaboration
Introduction: In an age where digital platforms dictate the trajectory of musical careers, a serendipitous collaboration between Frank Watkinson, a septuagenarian bedroom busker from the UK with a YouTube following in the millions, and Break Out The Crazy (BOTC), a dynamic duo from New York known for their genre-blending sound, has captured the hearts of listeners across generations. This partnership, sparked by a simple Instagram DM on February 3, 2025, showcases the power of the internet in fostering musical innovation and cross-generational camaraderie.
Article:
In the serene backwaters of the internet, where music seeks its audience rather than pursuing it, an unanticipated collaboration took root. On February 3, 2025, Jack Olmsted, an admirer of Frank Watkinson, reached out via Instagram DM to Katya Diaz and Chris Hierro of Break Out The Crazy, suggesting a creative collaboration with the 71-year-old singer/songwriter known for his living room performances that have captivated over a million YouTube subscribers.
BOTC, intrigued by Frank's indie-folk ethos, responded promptly, leading to an exchange where they discovered Watkinson's cover of Chris Isaak's "Wicked Game," which had already resonated with thousands.
The dialogue quickly moved from digital messages to an audio call, where the groundwork for a collaboration was laid. The mutual respect was palpable; BOTC suggested adding harmonies to Watkinson's song "You Make Me Smile," despite the challenge of working with his live, single-file recordings. Watkinson, known for his collaborative spirit, was open to the idea, his response reflecting a blend of generosity and practical advice.
By February 17, BOTC had shared their rendition of "You Make Me Smile," transforming it into what Jack described as a "spiritual experience." Watkinson was thrilled, immediately agreeing to feature the cover on his channel, promising to link back to BOTC's work, thus creating a loop of mutual promotion and artistic appreciation.
This collaboration is emblematic of a broader shift in the music industry: a move away from the traditional hierarchies and towards a more egalitarian, interconnected soundscape. Here, veterans like Watkinson can share the stage with fresh talents like BOTC, where the music speaks louder than the platform or pedigree.
The partnership also reflects a broader narrative of music's power to connect across divides—be it age, genre, or geography. It's a testament to the evolving music scene where authenticity and collaboration are prized over commercial viability alone.
In-Depth Summary:
This article explores the nuanced collaboration between Frank Watkinson, a seasoned musician with a significant online following, and Break Out The Crazy, a contemporary music duo known for their innovative sound. Initiated through a simple social media message, their partnership evolved from mutual admiration to a tangible musical project, showcasing "You Make Me Smile" with added harmonies by BOTC. This story not only highlights the personal journey of these artists but also underscores the changing dynamics of the music industry, where digital connectivity allows for collaborations that would have been unthinkable in the pre-internet era. Their story is a vivid illustration of how music can transcend traditional barriers, fostering a culture of creativity, respect, and shared success.
###
Honoring the Magic: How Break Out The Crazy Harmonized with Frank Watkinson’s “You Make Me Smile”
A Conversation with Katya Diaz on Collaboration, Emotion, and Raw Musical Beauty
In the digital age, where music often finds its audience through serendipity rather than strategy, the collaboration between Frank Watkinson, a 71-year-old UK-based bedroom busker with a million-strong YouTube following, and Break Out The Crazy (BOTC), a New York duo known for their genre-defying sound, stands out as a testament to the power of connection. Recently, Jack Olmsted spoke with Katya Diaz of BOTC about their decision to add harmonies to Watkinson’s heartfelt track “You Make Me Smile” and the intuitive process behind it. Below is an edited excerpt from their conversation, revealing the emotional depth and artistic respect that fueled this partnership.
Q: What was the process of putting your harmonies to Frank Watkinson’s song, “You Make Me Smile”?
Katya Diaz: Well, you know, when I first got your message, I was hesitant because we get a lot of messages asking for all kinds of bizarre things. Some of them require us to pay for something, or they feel like scams—there’s a lot of stuff on the internet. So, I was hesitant at first, but I immediately softened when I looked at your blog. Seeing Frank's work, I don’t even know how to describe the mastery because it’s not something purposeful on his part. There’s a delivery, an intensity, and a realness to how he performs songs—whether they’re someone else’s or his own—that is consistently and incredibly impactful.
I don’t know who could be impervious to his performances, but I certainly wasn’t. I found myself in tears, and when I read the comments, I agreed with everyone—everybody is just blown away by what he’s able to emit with his songs and with others’. He transforms them and delivers them with everything they need, plus things you didn’t even know they needed or that you could feel from some of these songs. That’s a mastery and a magic that I don’t even want to know how, why, or where it comes from—we just sort of bask in its light.
So, I went through some of his songs and thought, “Okay, what do I think we could possibly contribute to this magic without taking away from it?” I looked for something that spoke to my heart, because I’m a big lyric and melody person. I watched some of his other collaborations, and I have a lot of respect for everything he does. Then I saw his more recent song, “You Make Me Smile,” and it really spoke to me. The lyrics spoke to me—I’ve written similar songs that are in the vein of being very personal and deeply connected to the emotion of love and missing things. It was easy for me to tap into that emotion, but to meet him where he was—that was the real honor. His delivery is just, you know, I fail to come up with the words, which is a good thing because I usually have a lot of words.
I showed it to my husband, Chris, the other half of Break Out The Crazy, and he got it right away. He said, “Oh, I mean, he’s amazing,” and he was like, “Sure, let’s do it.” Normally, the way we approach something like this would be very methodical—we’d record it ahead of time, make it perfect and do all this other stuff that we do as professional background singers, which we do all the time for recordings, records, for our clients. But this song has a rawness that we didn’t want to ever disrespect.
So, we literally just sat down, had the words there so we could make sure we sang the right words, and tried to memorize his phrasing more or less, but we were never really too strict about it. That was the first take that you saw—the only take we recorded—and it had what we felt it needed to match his sentiment. The planning of the humming at the beginning was just to allow him to have a moment where he was singing by himself, and then we would come in and put our colors to it.
I love harmony—anyone who knows me as a singer knows I’m a big harmonizer. I started out as a background singer, and it’s my passion aside from songwriting. That was why we chose to do that. My husband plays keyboard and piano and stuff, but I thought the beauty of Frank’s guitar and his vocal with the guitar—I didn’t really want to mess with it as far as adding music. I thought the simplicity of it was its beauty, and to just give it a little of our color without picking away or trying to distract attention was the goal.
I really wanted the attention to be on the lyric and on him, and that was the way I could think of that would most honor the beauty of the song. It was hard to sing it without crying, I’ve got to be honest, because I’m so deeply connected to lyrics and stuff when I hear them. So, again, it was beautiful—it was the one I thought we could honor in our way, and hopefully that comes across. It came across to me when I heard it.
Q: One take? That’s how Frank records his songs.
Katya: Exactly. That’s why we did it like that. It’s another way of honoring him, you know? We had to listen to it a couple of times before recording it just to make sure that we weren’t too off of the cadence, but once the camera was rolling, we were like, “Okay, if it’s off by a little bit, then it’s off by a little bit, and so be it.” We got to honor his rawness without coming in and messing that up by making it too on the grid. There’s a magic in that, and you don’t want to mess with that—don’t mess with the magic. You’ve got to recognize it so you know what not to mess with.
Q: How did you feel after recording your harmonies over Watkinson’s raw, one-take performance?
Katya: Oh, you know, without trying to be over-dramatic, it’s like a spiritual experience. When you sing with more than one person, there’s a study that’s shows when you start to play with people as a musician and sing, your heartbeats become in sync. I knew that instinctively because you feel that happening.
Now, when someone’s not in the room and it’s pre-recorded, you’re trying to capture that feeling where you’re channeling the original sentiment of the song and the original vibe of how it was recorded—the words, and everything else. So, in channeling that, you sort of go into a zone where you’re literally just trying to pick up on the sound vibrations. You’re a little bit in a trance of the music, the words, and the melody.
Chris and I have been singing together for a long time now and are very much used to singing with each other, so to work out the parts was super fast. Maybe the bridge we had to finagle a little bit because we wanted to do something a little different there, but in general, it was just going into that happy, happy trance. When the song’s over, I guess maybe that shows that we’re still somewhat in the ether of that—the embers of that trance—and that’s probably what you perceived.
We’re kind of unaware of it because we’re so used to doing it often, but it’s special. You always feel something that’s very magical when you’re able to sing with someone and sing something that’s beautiful like that—it really makes a difference, the beauty of the song.
Q: When you finished, did you know that that was going to be it—that there would be no other takes, that you couldn’t get any better than this?
Katya Diaz: We didn’t know that, no. We took it because we wanted to take a listen to it first. Sometimes, every now and then, the recording isn’t right, or the levels aren’t right, or you messed up so much that it’s just like, “Okay, this is just not good.” We listened to it, and we heard the moments where we were a little bit out of sync, and I was just like, “I don’t want to fix that, I love it.” I was thinking of Frank, I was thinking of the words, I was soaking in the beauty of the song, and you know, I could do it again, but there’s the rawness of how he records, and I really wanted to match that. Our mistakes and all—you know, make it match him, if anything. That was my thinking, anyway.
Q: What were you thinking or feeling when you listened to it back for the first time? Did you feel that it captured the magic of that moment?
Katya Diaz: Yed, I did. Because once we got the technical part sorted out, like making sure that we weren’t singing the same note and stuff like that then we could just enjoy his performance and try our best to meet him where he was in honoring the song. So, when I heard it, I was like, “Yeah, that’s what I felt,” and I wasn’t distracted by anything else at the moment—I was fully in it.
I don’t take any credit—it’s the song that inspires me.
This interview captures the essence of BOTC’s approach: a blend of reverence for Watkinson's unpolished artistry and a commitment to enhancing it with their own emotional authenticity. The result is a version of “You Make Me Smile” that retains its raw magic while glowing with new harmonic light—a collaboration that bridges generations and geographies through the universal language of song.
Diaz’s words paint a vivid picture of the recording session: a moment of sonic alchemy where technical precision gave way to an intuitive, almost transcendent connection with Watkinson’s original performance. The result is a cover that not only honors the song’s simplicity but elevates it into something ethereal—a shared heartbeat pulsing through the music.
Choosing to keep their first take—imperfections and all—was a deliberate nod to Watkinson’s own one-take philosophy, resulting in a cover that feels both reverent and alive. For Diaz, the playback affirmed that they had captured the song’s magic, a sentiment echoed by listeners like Olmsted, who found the result transcendent. This collaboration proves that sometimes, the truest art lies not in perfection, but in the unfiltered beauty of the moment.
