When it comes to songwriter reality, truth is better than fiction.

At least, that’s how it’s worked for Virginia To Vegas principal Derik Baker, who’s scored more than 260 million streams (and three SOCAN Awards) since he began the project back in 2014.

“I think every good song comes from a true story – or at least a little bit of it,” says former tour guide Baker, a few weeks after releasing his second EP of 2020, don’t wake me, I’m dreaming, and his latest single “Palm Springs (the way you made me feel),” following the earlier A Constant State of Improvement. “Where I really started to connect with people that were fans of my music was when I started to tell stories that were more authentic to myself. So, it’s an anomaly – the more specific you are to past experience, the more it touches people.”

Ergo, the backstory to “Betterman,” a milkshake-smooth pop ditty that’s earned Baker 10 million streams thus far. “‘Betterman’ is the true story of me driving home from Los Angeles with my tail between my legs, after a bad breakup and at a low point in my life,”  Baker recalls of 2019’s re-location to Toronto. “I had my dog in the passenger seat, and my car filled with furniture and pictures, realizing that I was going to move back into a bachelor apartment and start my life over.”

Baker says the melancholic nature of the experience offered a particular challenge in terms of appealing the song to a pop audience. “How do you tell it in a poetic way, that’s catchy, and for people sing along to?”

And then there’s his biggest hit, the 50-million-streams-and-counting “Just Friends.” “That song is a story about summer infatuation in Toronto,” the Virginia-born Baker explains. “The song idea is that I was living in L.A., but writing a song about Toronto while I was in Toronto, [about] missing Toronto.

“How do you tell it in a poetic way, that’s catchy, for people sing along to?”

“There’s a line in the song that says, ‘So why don’t we go out and get a drink in the west end,’ and the initial version was, ‘Why don’t go get a room at the Westin,’ as I was talking about the Westin Harbour Castle hotel on Queen’s Quay. The song’s about how you’re having an awesome summer day, being on a boat on the lake, you know, that feeling when you’re in Toronto, feeling a little day-drunk, and having a really great time with someone that you’re infatuated with.  So, it was trying to capture that emotion.”

The Wax Records artist, responsible for such Canadian Top 10 hits  as “We Are Stars (featuring Alyssa Reid),” “Selfish,” and “Lights Out,” says he prefers to write with a team.  He’s established a coterie of collaborators that includes professional songwriters Mike Wise, Justin Alexis, David Charles Fischer, Geoff Warburton, and Nathan Ferraro.

“Everybody brings something different to the table, whether that’s melodic output; or having access to cool vocabulary; or being able to check the math on something; or structure the overall arc of the story,” says Baker, who’s formed a partnership with Republic Records for this new EP. “Everybody has different strengths and weaknesses. I find that with my  group of friends, what we do together complements each other, and makes my best music, in my opinion.”

And what does Baker consider his own greatest strength? “I really like context, and story, and thinking of colour – like, let’s paint the picture of this specific situation,” he replies. “My friend Geoff is really good at articulating on how to say things that make the most sense, while my buddy DCF – if we can’t get that one perfect rhyme, he’s like a workhorse, he never gives up. So it’s kind of neat.”