The Freewheelin’ Ross Wylde

When Ross Wylde ’22 was 16, he was touring up and down the California coast and through the Midwest as an opening act for what he fondly calls a “traveling circus.” While his parents didn’t love that the tour whisked him away for nearly half a year, on the road was where Wylde started writing his own music. “I would meet a lot of musicians in all these towns and learn a lot about different fingerpicking styles and how other people wrote their songs,” he says. “I scooped up a lot of stuff.”

Now 23, Wylde is effortlessly cool, rocking an embroidered denim coat as he sails around Santa Clara on a white motorbike. A frequent performer in the area, you might catch him skirting by you on the street with his guitar strapped to his back. He’ll tell you he wishes he could strap a baby grand on his back, too. The piano is his weapon of choice, and words are his favorite instrument.

Raised on old-time-y rockers and Pablo Neruda poems his mother, a poet herself, read to him at bedtime, Wylde learned how to make his own prose sing. He embraces the folk tradition entirely with its rolling melodies and stirring lyrics. He’s released two albums: in 2019, In Retrospect, and in 2021, 2nd Impressions. It’s not hard to recognize the traces of his favorite artists—Elliot Smith’s soft-spokeness, Nick Drake’s rhythmic guitar, Bob Dylan’s mannerisms—that he’s repurposed for himself.

Growing up, he took advantage of the tourist nature of his coastal hometown, Mendocino, to do his first crowd work on the side of the road.

A member of that traveling circus, which was made up of everything from trapeze artists to silk aerialists, heard Wylde strumming on the street and asked him to join the tour. For several months, Wylde toured the country, honing his musical skills and picking up the harmonica along the way. He even took on a stage name, which helped him open up as a performer—from Ross MacNeil to Ross Wylde he went.

But education was important to him. Wylde’s next stop would be university, Santa Clara in particular, to pursue a degree in business.

But the opportunity of a business education isn’t without its opportunity for the arts. At a gig for Santa Clara’s student-run literary magazine The Owl, Wylde knew nationally-revered slam poet Mighty Mike McGee was in the audience. “I was so nervous,” Wylde says. He performed a fan favorite called “He Died in Dreams,” which tells the struggle of moving on and trying to find your way after you’ve lost it. Lost time is something tragic, he sings, but to waste it is a sin.

After the show, McGee approached Wylde to tell him how much he liked the song. “If Mike McGee thinks it’s good, then I should probably release it,” Wylde remembers thinking. Admittedly, he’d never seriously entertained the idea.

With a USB microphone and a bit of trepidation, Wylde recorded his music, using his dorm in Casa Italiana as his studio. “Some of those tracks on that album—and you can quote me on that—sound really bad because of the way I recorded it,” he says. “And both my vocals and sentiments in there sound so young to me now—but that’s the beauty of art. You can tell what period someone is in their life by listening to their songs.”

Those songs became Wylde’s first album In Retrospect. He bared his old soul, lamenting love lost and unrequited, not without references to Greek mythology and California’s natural beauty (he’s a big hiker). Today, “He Died in Dreams” has garnered over 560,000 streams on Spotify alone.

His public vulnerability and easy disposition caught the eye of the film producers behind indie film 116 MacDougal, which tells the story of the Greenwich Village café that inspired many East Coast folk musicians in the 1960s, including a young Bob Dylan. “I was in Benson when I got this call saying they wanted me to play Bob Dylan in a movie. My first thought was—that’s weird, I’m not an actor,” Wylde says. But he jumped in headfirst anyway.

He flew across the country to record the soundtrack and perform with his Pittsburgh-based cast. One performance landed him in front of Smokey Robinson: “I was singing ‘Blowin’ in the Wind’ and I saw him in the crowd, singing along. That’s been the highlight of my music career so far.”

The pandemic indefinitely shelved the film. “But we got a lot out of it,” Wylde says. “It was less a movie and more an artistic project.” More, it reaffirmed Wylde’s passion for music and songwriting going forward.

“I started getting emotional about things that didn’t used to make me emotional,” Wylde says, remembering how he started writing his next album 2nd Impressions. The album was his reflection on history, both his own and the world’s. Sprinkled among Wylde’s meditations on growing up and moving on are songs like “Ballet In the Headlights (It’s a Sin),” inspired by the 1980s AIDS crisis, and “Christiana in Red,” which takes place inside one of the earliest color photographs.

Kirk Glaser, the faculty advisor at the student-run literary magazine The Owl, where Wylde was editor-in-chief during his senior year, knew Wylde was a major talent the first time he heard him play. “It just blew my mind,” Glaser says. “He’s got that stage presence that instantly shines forth.”

“He’s truly an inquisitive thinker and creator,” Glaser says. “He’s got all this talent, and yet, he’s just really interested in other people and their talent.” When he wasn’t onstage, Wylde was busy organizing the Coffeehouse, The Owl’s quarterly revue that grants students a platform to showcase their art. About 150 people packed into the Forge Garden in May 2022 to enjoy the show Wylde produced. Of course, Wylde got Mike McGee to emcee the last show he’d play as a Santa Clara student.

After graduation, it’s off to Seattle for Wylde. That’s where the beat generation is reviving, he says, and where hiking is world-class. With his pilgrimage to the Pacific Northwest comes a musical fork in the road. Maybe he’ll return to the basics, he thinks, just him and his guitar against the world. Maybe he’ll join a band. All he knows for sure, though, is that he’ll always be playing and writing.

Success as it has come didn’t come overnight, Wylde knows. That first album was built of songs old and new, and was years in the making. “I wrote hundreds of really bad songs before I wrote anything good.” Wylde says. “I’d tell my younger self to write more songs. The more bad songs you write, the quicker you become a better songwriter. And I’m still not where I want to be, but life is about creating art. I’m still evolving.”