Leslieville Lives; Stories from the ‘Ville – Ryan O’Brien

Meet Ryan. I first crossed paths with Ryan about 2 years ago walking my dog. He had just rescued his dog, Junebug, and she was having a grand ole time barking up a storm in Sunshine’s face. I could see he was in the throes of training her. We exchanged a few pleasantries and went on our merry way. We bumped into each other numerous times over the next few years, chatted a few times; the usual small talk passing on the street or in the dog park. It wasn’t until recently that I got talking to him more in depth one day in the park. Mind blown.

Ryan hails from the ‘projects’ ( better known here as Community Housing) in bordertown Chippewa, a suburb of Niagara Falls. The only child of a single mom, Ryan’s move to Chippewa was his third in just a couple of years. It was Halloween night and they were greeted with ‘Fuck You Asshole’ on the window of their house. “That kind of summed up life there then. The area was incredibly rough and poor. The government wasn’t around to police much except to raid houses for dealing, manufacturing drugs or prostitution. Organized crime pretty much ruled the roost. Chippewa was a microcosm of bordertown hopelessness, just past the bridge from waterfront mansions. When you never see examples of hope or a future, you just do what you have to to survive.” Ryan saw his first dead body at the age of 8. The first of many.

As a young man, Ryan’s not sure how he managed to cope in the poor and violent surroundings. He modelled up til Grade 9,  but as the ‘faggy model kid’ he was beaten up with regularity.  He took up skateboarding & cycling at the age of 8 and as the bullying got worse the more hardcore he got. “For kids who had no parents or one who worked 2 or more jobs to get by, most of us were just hanging on for dear life. I’m sure if I hadn’t had switched schools in Grade 10, I’d be dead. That move changed my life.” Before he was 16 Ryan had seen a number of beatings and shootings and stabbings that led to death. “I’d lost many friends to violence.” By high school he was sporting a 2 foot mohawk paired with cheetah print fun fur vests, 20 hole boots and leather adorned with wood screws. “We were both feared and targeted.”  He went to Westlane High School, a school where you went if you wanted to be a business professional. “I didn’t fit in. The weirdos went to the art school – which is where I transferred to in grade 10… and thrived.” His stepping stone to a better life was working on the school production of a post-apocalyptic version of Godspell. He fell in love with theatre and all its workings. His theatre teacher, Kevin, became a father figure and still calls Ryan ‘son’. The principal was the president of Theatre Ontario, and organized a group of kids to write, produce and perform a play to enter into a theatre contest. ‘Classtrophobia,’ an avant garde piece was the end result, which won them the contest, where they performed at (the then) O’Keefe Centre.  Ryan found his calling and his school marks skyrocketed.

He furthered his studies at Humber in the Theatre programme, but his OSAP ran out at Christmas. In 1992, at the age of 17, he shacked up with a friend and started working at Stainless Studios, a tattoo and piercing parlour. “I started out sweeping the floors, cleaning up, learned to make body jewelry and eventually graduated to piercing”.

 A few years later, a friend of Ryan’s from CHUM radio walked in and wanted a tattoo. He was a personal security guy there. He says ‘Hey, wanna trade jobs?’ and Ryan laughs, ‘Sure’. They actually make the switch and Ryan’s life changed- again- on a dime. “5:30 am mornings to go out with the early news crew was a serious change of scenery, but I loved it. I was eventually working as security and crew.” Not long after, MuchMusic started and Ryan got to hobnob with A-list celebrities such as Madonna, Janet Jackson, Prince, Cher, John Travolta, the list goes on. Eventually he became the security supervisor. In 1996 the ‘Boy Bands’ started making their mark; The Back Street Boys and a lesser know foursome called *NSYNC. Not very well known in Canada at the time, Ryan didn’t have much to do in the way of ‘security’. “Not like with Mel Gibson where we had to do bomb sweeps“, he laughs. After receiving their first gold records they wanted tattoos to celebrate. In the waiting area, Chris Kirkpatrick from the band turns to Ryan, pointing at Justin Timberlake, while he was singing along to the radio and says, “He’s going to be a giant fucking superstar.” Well, we know what happened there.  

For the next year and a half, Ryan is hanging with *NSYNC in Toronto, Detroit and back in Hollywood. They become great friends and he and Chris, from the band, start up a clothing company together called FuMan Skeeto. “I was the VP of Online marketing and development in 1999. Chris wanted Dave (Ryan’s friend/work partner) and I to become millionaires”, he smiles. They moved to Hollywood on Halloween (the 2nd move in his life on that fateful date) 1999. Just as the clothing biz and the band are reaching their zenith, 9/11 happened. As a conscientious objector, “I didn’t want to pay taxes for a war I didn’t believe in”, and Ryan returns home. Still working for *NSYNC via Toronto, Ryan gets a call from CHUM one day. There’s an opening at MuchMusic  in web design. Over the next few years, he moves up the ranks from Art Director at CHUM (then owners of MuchMusic, CityTV, CP24, Bravo! and Space), to Creative Director of Digital on all their networks in 2007, when CHUM was bought by CTV . In 2010, he founded the User Experience group and was director managing a staff of 25. In 2011 CTV was acquired by Bell Media.

In between the career rises and changes, Ryan reacquaints with an old crush from his piercing days in 2007. Amber was a guest artist at New Tribe Tattoos & Piercing visiting from Montreal on Much Music. They marry in 2009, she moved back from Vancouver and they set up house in Parkdale. After witnessing several deaths in and around the area, Ryan suffers from an anxiety attack. “It was all too reminiscent of my growing up days. I’ve lost 2 friends a year since the age of 12 due to violence [and addiction] so we moved to the east end. First Cabbagetown – where life seemed so nice, friendly and easy – and then further east to Leslieville, where we bought in 2010. It was the first time I realized I could choose to live somewhere nice”.

Due to a changing media landscape, in 2015 Bell Media gave Ryan’s entire department plus about 350 people worldwide, their walking papers. Having had a life of unstable, but interesting work, Ryan moved directly from his position at Bell Media to creating a clothing line for cyclists called ‘Hustle and Cuss’, which included T-shirts, hoodies, bike wear, toques, the lot. “I had a few connections in the cycling world in Cabbagetown. I had co-founded, with neighbourhood friend Wil Mills, the Cabbagetown Cycling Club in 2009. I still have the clothing line, which does well, but I’ve now ventured into my own creative freelance business and work with branding, e-commerce and creative for entrepreneurs.”


Despite his success in life, Ryan was recently diagnosed with PTSD, not surprisingly, from his exposure to violence and death at a young age. More recently, the loss of his best friend to a rare form of degenerative genetic disorder has added to the tough hand he was dealt. Luckily his perseverance and personality and support of his mom saw him through to the other side. Covered in tatts and stretched out ear lobes from the body mod days, Ryan is the nicest guy you’ll ever meet. They say only a few percent of kids can rise above the hard times they grow up in, in their youth (I can’t write half the stories he told me) and Ryan is one. If you see him on the street say ‘Hi’. Maybe he’ll tell you a story or 2. And trust me, you will want to listen.

*Older photos provided by Ryan

  • Jo-Anne Cameron

    December 5, 2016 at 10:22 am Reply

    awesome story again…….. it never ends and I marvel at how interesting peoples lives are, though hard we persevere and thrive……. Thanks Diane and Ryan……

    • diane

      December 5, 2016 at 10:40 am Reply

      I know eh? People are amazing. He’s such a nice guy. I had noooo idea.

  • Stephen Findlay

    December 5, 2016 at 10:38 am Reply

    Fantastic. So uplifting!

    • diane

      December 5, 2016 at 10:40 am Reply

      I love these stories. They make me appreciate my rather ‘privileged’ life.

  • Jim Smith

    December 5, 2016 at 1:49 pm Reply

    What an interesting (and scary) life, with a great present. Diane, thanks for these wonderful portraits!

    • diane

      December 5, 2016 at 3:01 pm Reply

      Thanks Jim. He’s definitely one who ‘got away’. An amazing turnaround. I love learning about people I think I ‘know’. Like you too! What a surprise learning all that I did during our interview. And everyone’s interview. Never judge a book and make assumptions eh? Lesson learned.

Post a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.