Kendra Boyles is a part-time multimedia artist and a full-time wild woman. You may recognize her as the roller skater who glides into local venues and brings everyone onto the dance floor with her contagious enthusiasm. Kendra has contributed to Toronto’s jazz world through her work for local musicians including event marketing, album covers, logos, posters, and live event video production. Despite a series of personal losses, she finds herself on the precipice of a new life chapter and is dreaming even bigger than before.

JIT: How did you get connected to jazz and other live music?
I had one of those dads who would quiz me whenever a song came on the radio — “What band is this?” “What’s this song called?” “What album is this one from?” so I grew up listening to a lot of dad rock. In high school I befriended musicians who invited me to shows and festivals. Our friend group of tight-knit artsy weirdos were pretty much all on the Arts Council and together we helped to create and market many of the arts, music, and theatre events at our school. Teenage me would take on even more extra-curriculars for fun and record shows, do photo shoots, and make album covers for my friends’ band. Through high school and university, I was often the one documenting events to keep some kind of time capsule of the moment.

Post-university and a few years into working full-time as a graphic designer, I moved to Vancouver in 2016 to experience adventures in the mountains. From 2018 onward, I got to volunteer on the set of some music video shoots for my friend and employer at the time, Connor McGuire. Connor had me on a handful of music video sets to assist with odd jobs. One of the coolest ones was for Mother Mother’s “Get Up” music video. Then, the pandemic closed the world, and the small Vancouver firm I was working for went fully remote. One morning after my microphone glitched to be super quiet on the daily video call, a friend/coworker sent me his favourite jazz album, “Quiet Kenny” by Kenny Dorham. That was my first time really engaging with jazz. During the eerily quiet weekend mornings of the lockdowns, I would get up early to steal a couple hours for myself. I would listen to jazz, drink a cup of coffee, and practice drawing. Kenny’s horn on “Alone Together” felt so hauntingly poignant at that time. Throughout the first six months of 2021 I endured the deepest depression of my life (a relatable story, I’m sure) and it was jazz, drawing, and roller skating that kept me going. In July 2021, after a dramatic life-upheaval; a loss of self and the separation from my ex-fiancé, I moved home to Ontario to recover, living with my folks through the remainder of the pandemic.

Fast-forward to June 2022 — I was getting back on my feet again and had just moved to Trinity Bellwoods area. One day I wandered into a moody coffee shop on Queen Street that looked like something straight out of a movie set. I felt an immediate connection with the lovable venue owner, Sevag, who told me to check out Doghouse Orchestra at the Cameron House on Sundays. Around the same time, some new climbing friends brought me to the Toronto Jazz Festival where I saw Mosquito Bar for the first time. Another university friend told me to check out Swing Dance Tuesdays at Drom Taberna. Serendipity brought myself and a fellow dance student, graceful Kate Lam, to the same events and we were fast friends. That September 2022, Kate introduced me to a ton of people in the swing dancing scene, and I started befriending a lot of musicians too. With the help of this newfound community, I was finally starting to reconnect with my sense of self and felt safe to be who I truly am.
I volunteered for the Kensington Market Jazz Festival, moonwalking down Augusta on my roller skates to collect proceeds for the musicians. Not long after KMJF, I started volunteering with Jazz in Toronto to submit videos from jazz events. That helped me build trust and a reputation in the scene, and musicians started hiring me to operate a camera for them at their shows. With the support of friends who would lend me their gear for the occasional gig, I steadily saved up for a second-hand Fuji XT4 in Sept 2024 and began doing freelance videography for live events part-time. Last July 2025, after a period of serious burnout, I quit my full-time 7 year corporate job working remotely as an Art Director and started freelancing full time, almost entirely for musicians. My word of mouth was so strong that I was never without work. I feel like the community really held me through this past year and I took on so many projects that are dear to my heart. I returned to my natural state of making album covers, recording live shows, and editing fun videos of my friends. They say that you’ll become happiest if you go back to doing those things that you did for fun in your youth, and nothing could be closer to the truth in my case.

JIT: How did you discover your love for photography / videography?
Back in my high school days, I took photos and videos of my theatrical friends on a regular basis with a little red point-and-shoot digital camera. I would do overnight turnarounds of 720p edits to post on Facebook that would only get 10 likes. The videos were insanely cringey and edited in Windows Movie Maker, but those silly videos helped me get a handle on comedic timing, pacing, and what to cut out vs leave in. I would make little documentaries or strange disjointed narrative videos out of footage from our family vacations, which would be so riddled with inside jokes and obscure cultural references that they’re completely unwatchable.

During university I was in the joint design program with York/Sheridan, but I took every elective in motion design and film that I could register for. Once I was out of school, I was immediately disillusioned by the corporate working world and began plotting my “escape plan” to become an adventure videographer and move to the mountains. I went to workshops at the Hart House at the U of T and took a handful of weekend courses with the Liaison of Independent Filmmakers of Toronto (LIFT). I often took trips to the Niagara Glenn and Tobermory with my friends and made rock climbing videos in my spare time. I kept up the same type of video projects after moving to Vancouver and meeting a brand new group of climbing friends. I haven’t been on many climbing trips since moving back to Toronto, but when I do I almost always bring a camera.

JIT: How do you approach these mediums differently and what do you like about each?
I’m not much of a photographer anymore, but there was a period in my early 20s when I was taking almost exclusively photographs. I would idolize adventure photographers like Jimmy Chin who has worked with National Geographic. My day job at the time had me taking flash-photography headshots of new hires, and I spent many hours in Photoshop learning how to make people and buildings look most appealing for engineering project proposal documents. I still occasionally do some photography, but time-based storytelling through video and animation was always a bigger draw for me.

Film is the ultimate culmination of all mediums for storytelling —the visual, auditory, and time-based aspects let you give a more complete picture; a longer look. I like the slowing down of time that comes with video editing, and the ability to travel backwards and forwards and invite the viewer into the story. I want them to slow down and be curious with me. I look forward to a day when we wean society off this landscape of attention-span depleting short form video “content”. What the world really needs is richer stories, so I do my best to communicate that in the context of mini-documentary style interviews with musicians. This is a format I’ve been using more for social media, so they are usually only one or two minutes long, but the aim is to give more context to the work and give the artist that time to go deeper on different facets of their art through the series format. I would someday like to take on more long-form projects, perhaps journalistic and/or documentary work to explore ideas more deeply.

JIT: Who are some of your favourite Toronto musicians and why?
I see so much talent on a regular basis. I refuse to choose favourites! But I love acts like Mosquito Bar and KUNE who celebrate and create the uniqueness of Toronto’s culture. Toronto, if you haven’t heard, is the MOST multicultural city on the planet. ON ALL OF EARTH. Our scene is made up of musicians from all over the world, and the beautiful fusions and playfulness between the different cultural influences creates sounds that feel familiar and new at the same time. THAT is what brings people together. THAT is the stuff that forms meaningful bonds between people across cultures. Toronto’s music landscape is full of novel experiences every day of every week. The Tap Room Gang will transport you to the 1920s over $5 beers on a Monday. The Happy Pals will send you and your grandma on a trip to New Orleans on a Saturday afternoon without ever leaving Grossman’s Tavern. Doghouse Orchestra will have you headbanging and jumping up and down to a Paul Simon song at 2am on a Sunday. None of this is anything you might expect if you weren’t already familiar with what’s happening out here.

I would argue the case that the “capital S” Small Time scene—coined by Corin Raymond—is where the real magic is happening. I have always felt that the most important music is the music made by my friends. I’ve had that mantra since high school. That is not a vain or delusional assertation. Within the context of our community and the lives of everyday working-class people, these songs and these stories are everything. The experimentation, the quality of the stories, the raw talent and disciplined playing within Toronto’s jazz scene does not hold the faux plastic sheen of over-produced big industry music. It is REAL. It is HUMAN. The music of working artists who play multiple shows a week and hone their craft —that is the highest quality music you’ll ever hear. It’s hard not to just list my friends and their projects, so I’ll say this—I think everyone who contributes their voice to this scene should know how significant they are to the flourishing of everyday people, and the overall beauty of our city. Your influence and impact go so much deeper than what a streaming site’s play-count could ever show. Keep going.

JIT: What are some of your favourite Toronto venues and why?
I guess it started at the Cameron House. That place is something like a church for me and so many others. Drom Taberna is another center for all types of musical acts, all days of the week. “Drom is home” as they say. I’ve shot many a late night at Drom, biking home with a bag of video gear in tow, listening to the birds greeting the dawn. Grossman’s Tavern is always a classic spot with some of my favourite blues acts. The Local on Roncesvalles never fails to brighten my spirits, and every time I go to the Bell & Beacon Room in Parkdale, I seem to meet the most interesting and wholesome people there. The Tranzac Club is also a total gem in the scene. Don’t forget the Monarch Tavern! I wish I could afford Jazz Bistro but last time I think I ate entirely olives. More recently I’ve been checking out the east side of town; The Only Cafe, Sauce on Danforth, and Noonan’s Irish Pub are all worth the TTC trek. There are seriously too many great venues to mention.

Dina’s Tavern has amazing jazz on Mondays and Swing Dance Tuesdays with other friendly faces throughout the week. If you’re into blues, I just booked a new blues dance and jam event happening on the occasional Wednesday at Dina’s. If you’re interested, the next one will be August 26th with a blues dance lesson starting at 7pm!

JIT: You recently went through some professional struggles with your equipment being stolen – how has this shaped your plans for the future?
June and July of this year flipped my life upside down in a way that I didn’t expect, but upon reflection, perhaps I needed.

I’ll set the scene a bit — I had just gone through a breakup at the end of May, so we had to give up our apartment. I had just moved back in with my folks around mid-June to recover…again. So, you could say I was already going through a bit of a rough patch. I was working a contract gig up north and had my first day off in two weeks. I took the day to come back to Toronto for a gig on June 30th and parked our family vehicle, ‘Blue’ on a residential street near St. Clair West. On July 1st at 3:30am, three masked men dressed in identical hoodies stole the vehicle. My camera bag was in the locked trunk. Our neighbour’s security camera captured the incident. Luckily, police found the car somewhere on the east side of town a few days later. The thieves had taken my entire camera bag including two Fujifilm cameras and three lenses, accessories, batteries, tripods, etc. However, they did leave behind my audio recorder and interview microphones, so I was grateful to have those back.

Losing material things has a way of putting life into perspective, and with all the support and kindness that flooded in, I have never felt more rich in friends, family, and community. In light of these personal losses, I’m seeing this as a sign to slow down and reassess my path. I do have a new camera in my possession, but I have chosen to wind down my freelance practice to the occasional project to make space for a more full-time role that is more aligned with where I am going. I am still exploring the possibilities of what that might be.

Mike T. Kerr says he thinks that I am a natural documentary filmmaker. With over 12TB of video footage from Toronto’s music scene from these past 5 years, perhaps I will make one. I have more recently considered a path of becoming an arts and culture journalist, but who knows! I have also thought about becoming a teacher because I do enjoy mentorship, I have professional experience in multiple areas, and these kids need all the help they can get. Maybe I will do some combination of things. Ultimately, I hope to find a direction that will allow me to be of service to my community, interact with people more than machines, and still reserve my creative energy for my own visions. After 17 years of denying my dreams, I am getting out of my own way and finding my way back to my first love—painting and visual arts. Although the world knows me mostly for my design and video work, being a visual artist was always the identity I felt most aligned with. After all this time, I am revisiting that identity.
I am not yet sure what I will do next, but I am in an era of dreaming bigger than I have before and reimagining what I am capable of. If you’re reading this and you think you’ve got a role for me, let’s get in touch! keeprolling.ca/contact

JIT: Feel free to add anything you want to mention
Just want to give a formal thank you to Jazz in Toronto for offering the scene an alternative web venue for listings in this city. I have gotten to see so many new acts that I may not have seen otherwise by looking on your listing pages for “What’s On Now” and my favourite for planning ahead, “What’s on This Week”. I’m so glad your organization exists, and I hope it only continues to grow and shed light on artists who matter!

Much love. ~ Kenni

Video Work Samples

• https://youtu.be/b8cmFUHcisI?si=N5J02IfzEKpFyuEF
• https://youtu.be/b9TXreFXrV0?si=La4zNIyR4Gx8iNE8
• https://youtu.be/jxf1OlqBrfo?si=q0QI6BaCbFFSlZW7