The Toronto busker is making his mark one song at a time
By Nalyn Tindall
Kip James playing guitar on a beach in Algarve, Portugal. (Photo assets courtesy of sot.d_ / Instagram, graphic by Nalyn Tindall/CanCulture)
If you attended a concert at Budweiser Stage this summer or ventured outside the Rogers Centre after a Blue Jays game, chances are you’ve likely encountered the vibrant musical force that is James Flannagan, better known as Kip James. “Kip,” being the name he was almost given as a child, one he feels holds more star power.
Amplifier humming with live drum backing tracks boasting and his guitar and vocals soaring above it all, he’s hard to miss, and that’s exactly what he’s aiming for.
Kip James, a self-described entertainer, is on a mission to inject positivity into a world that often feels chaotic and divided, uniting people through the power of music. His performances go beyond mere entertainment; they generate a profound sense of unity that transcends the boundaries of spoken language in a way only music can.
Busking, the activity of playing music in the street or another public place for voluntary donations, is a testament to the unity art can inspire, even amid chaos. As James speaks of protests and counter-protests, he contrasts the harsh, divisive scenes with the harmonious interactions he fosters through his performances. "I'm doing the exact opposite,” he says. “The unity of it is so beautiful.”
Audiences can be found dancing together and singing along to his covers, a reminder that music has the power to bring people together in spontaneous ways. He hopes his music can remind people to come together, share their love for music and enjoy a moment of unity, no matter how different they may be.
His "make it happen" attitude is reflected in every aspect of his musical career, demonstrating his steadfast dedication to his craft. During the summer, he diligently tracked the major events unfolding throughout the city's core, recognizing the prime opportunities to connect with his audience. This led him to perform before and after every baseball game this season and for the crowds ushering out of the concerts of notable stars who played in Toronto this summer. James could always be found gracing the streets with his music and fostering a communal ambiance, riding on the good vibes generated by these events.
Among the memories etched in James' mind, one moment stands out. An older man, possibly in his late 70s or early 80s, approached with his daughter. "Can you play 'Pretty Woman' by Roy Orbison?" the man requested. James enthusiastically obliged, and the music profoundly impacted the man. Unbeknownst to James, this outing to watch a ballgame marked the older gentleman's first venture outdoors in a year, following the loss of his wife. James' performance had allowed him to hear his favourite songs and, for a brief moment, ease the pain of his loss.
Inspired by his dad’s classic rock CDs which made up the soundtrack of his childhood, James picked up the acoustic guitar at the age of 12. With determination and passion as his only guides, he taught himself the songs that formed the core of his musical upbringing. Many of these songs make up his busking repertoire today.
Kip James' journey would not be complete without mentioning his band, Fighting Chance!, which he formed during his university years. Acting as headman and bass player of the indie band, he has joined forces with his younger brother Joe on the drums.
The band members, including guitarists Dylan Duthie and Ryan Walsh, have diverse influences, each bringing their unique styles to the table. According to James, the band chooses not to subscribe to a particular genre; their repertoire spans classic rock to modern indie, allowing them to craft an eclectic sonic identity that resonates with a diverse audience. Their Spotify describes their sound as “90's radio rock with early 70’s powerpop,” while their Instagram bio identifies the group as “college radio rock revival.”
Their most recent single, “Spin Me Round,” has been warmly received by the many fans James has acquired throughout his busking endeavours. The band aims to release a single every month and plans to tour next year.
Kip James' journey isn't tethered to Toronto, however. Fleeing the cold weather, James has taken his act international. He recently made his way to New York City, busking in iconic spots such as Times Square and Madison Square Garden. He then headed overseas to play the streets of Portugal, serenading folks across the world. But true to his roots, he’s returned to Toronto, reuniting with Fighting Chance! to play a small tour throughout Ontario this month.
The path Kip James treads is marked by sheer dedication and unwavering persistence. He is far from content with standing still, instead tirelessly working to turn his dreams into a tangible reality. His performances, whether they be on the streets of Toronto, NYC, or Lisbon, are a whirlwind of good vibes, beginning with the first strum of his electric guitar and gaining momentum with each passing note. Keep an eye, or rather an ear, out for the eclectic busker the next time you find yourself at a major event downtown Toronto, and don’t be afraid to sing and dance along.