Ryman Leon was 22, working for his family’s business, and unhappy in a way nobody around him knew about. He made music privately, something he worked on while his friends built fan bases and toured and texted him to say, “hey, you should probably do this too.”
He didn’t. Not yet.
“It got to a point where I was really unhappy because it just felt like I was taking this more or less safe path,” Leon said. “I just got really depressed, honestly.”
The turning point came from his girlfriend, not from a label or a viral moment. She told him it was now or never. He was 22 turning 23. There would not be a better window than this one.
What made it hard wasn’t the risk. It was his family, specifically his dad. Leon is the oldest of four, the only son, and the idea of walking away from the family business felt, to him, like walking away from his father.
“I didn’t want to let my dad down. I think that was the hardest thing for me,” Leon said. When he finally brought it up, his dad’s response wasn’t disappointment. It was relief. “He was so supportive. He was like, yeah, do it, that sounds awesome.”
Still, something in Leon never fully let go of that fear. “I know it wouldn’t have been letting him down,” Leon said now, “but I wanted him to see it was successful. I guess because I took this risk.”
It paid off, though not in the way he expected. Leon had already put out seven songs, quietly, before his eighth, “Life’s Been Boring,” did something none of the others had. It didn’t explode overnight. It crept. A slightly better performance here, a little more traction on TikTok there, until a stranger posted the song and it went from slow build to full sprint in what felt like a single day.
“That was the most surprising thing ever, to be honest,” Leon said. “I didn’t expect it at all.”
More than 20 million streams later, “Life’s Been Boring” is the song most people know him for. But Leon had already built the engine that would carry him past it: a self-imposed schedule of releasing a new song every three weeks, no exceptions. He admits that pace sometimes cost him quality control in the early days.
“I made the decision,” Leon said. “This is what’s gonna happen.”
These days, with more resources behind him, he blocks out a week every two or three months to write and record in bulk, then steps away from music entirely until the next batch is due. The songs still land every three to four weeks. The panic just runs on a longer leash now.
That instinct toward honesty over strategy shows up everywhere in how Leon talks about his own catalog, especially his most personal material. “Somewhere in the Silence,” his most streamed track after his breakout, is a mental health awareness song that Leon said he never planned to write. He and a friend, Sam, wrote it in Nashville in 20 or 30 minutes. He knew immediately it would come out.
What he didn’t do next is arguably more telling than the song itself. The obvious move, he said, was to chase that same vein of vulnerability with follow-up after follow-up. He didn’t.
“I didn’t want to monetize and market a whole thing and make it my thing, and then that’s all I am,” Leon said. “If another thing happens like that, for sure. But I don’t want to put pressure on it.”
His July single took him somewhere different instead, a heavier, more rock-leaning sound than the acoustic indie his fan base tends to favor. The song is about Miami, where he grew up, and how unrecognizable the city has become for people his age. He folded that feeling into something that reads, on the surface, like a breakup song. “It’s not like a real story,” Leon said. “I think there’s some essence of truth in it.”
Denver fans catching Leon live at Black Buzzard this fall shouldn’t expect a straight run through the streaming versions of these songs. “We like to put a spin on the songs and make it a whole experience,” Leon said. “We love to tell a story with the setlist and really take the fans on a journey.”
There’s more coming than the live show. Leon is finishing an EP called “The Long Way,” a title he chose because it’s the only way he’s ever worked. No team of songwriters, no built-in machine, just him doing it independently the way he always has.
“There’s a lot of people that have a lot of help and have all the resources,” Leon said. “It feels like I’ve just been kind of taking, quote-unquote, the long way.” He sounds proud of it, not tired of it. “I’m excited for people to hear it, honestly.”
Ryman Leon plays Black Buzzard in Denver on Sept. 19. His EP “The Long Way” is expected later this year.
