At the 2026 YYC Music Awards, Bijaan and Jaiden Riley arrived from different corners of Calgary’s music community. In conversation with Afros in tha City, both artists traced the years of relationships, losses and deliberate choices behind their nominations.
Before Bijaan was playing South by Southwest or standing on the Coca-Cola Stage at the Calgary Stampede, he and his friends were making rap songs in northwest Calgary with software from Staples.
He remembers it clearly: eJay Hip Hop 5, inexpensive computer headsets and three kids recording in their bedrooms.
“We each went and got our parents to go buy us the program from Staples. It was like 50 bucks, and then we got these cheap little computer headsets and started making songs in our bedrooms,” he says.
One of those kids was Graydon Welbourn, now Bijaan’s manager. Another was their friend Jonas. Years later, Jonas’s younger brother Allih would become the subject of one of Bijaan’s most personal songs.
That early history gives some perspective to what otherwise looks like a remarkably quick arrival. “Jungle”, Bijaan’s first major introduction as an artist, is nominated for Rap Recording and Music Video at this year’s YYC Music Awards.
When Bijaan talks about his career, he does not sound like somebody who thinks any of this happened quickly. After high school, he left Calgary for university in Edmonton and later completed graduate school in Toronto. He spent roughly seven years in post-secondary education and became a chiropractor. Music remained part of his life, but the idea of building a career around it moved further into the background.
COVID changed that.
His family had given him a record player as a graduation gift and, during the pandemic, he began collecting the hip-hop albums he had loved growing up. Returning to those records forced him to confront something about the life he had built.
“I had this career that was now sustaining me financially,” he says, “but it wasn’t really sustaining me creatively or spiritually.”
Eventually, he decided he could not live with never seriously trying. What followed has been methodical rather than impulsive. Bijaan describes his approach to the industry as “being extremely patient while at the same time not wasting time.”
There were festivals across Canada before the first major release. There was NXNE in Toronto. This year brought South by Southwest, an experience Bijaan says helped him understand the scale of the music industry beyond Canada. It also gave him confirmation.
Surrounded by artists and industry professionals working at an international level, “we belonged,” he says. “It didn’t really feel like we were out of our depth.”
That confidence runs through “Jungle”.
Bijaan was born and raised in Calgary. His family is Indian by heritage, but several generations of his family lived in East Africa before Canada. His father’s family came through Kenya and his mother’s through Uganda. His parents were born in East Africa, immigrated to Canada and eventually met here.
Bijaan is the first generation of his immediate family born in Canada.
“You’re from all these places and you kind of fit into all these places, but you don’t really have one home,” he says.
For him, “Jungle” is partly about the third-culture experience. The feeling of being connected to several cultural histories without fitting neatly into any one of them. The song refuses the idea that he has to choose.
“Being in all these places kind of makes me uniquely who I am.”
The music video was built from that same sense of shared history. Directors Bhaveek Makan and Jashan Makan are longtime friends. Bijaan remembers making videos with them in junior high. His working relationship with producer Junia-T also grew from an older connection through Graydon.
The current nominations may be new, but very little underneath them is. “What I love most about hip-hop is the storytelling and our ability to tell stories in music,” Bijaan says.
Across Calgary’s musical landscape, Jaiden Riley is telling a very different kind of story. Riley is nominated this year for Indigenous Artist, Solo Artist and Emerging Artist. Her music moves between country, folk and bluegrass, but when she talks about the work, she consistently returns to storytelling before genre.
“I really just like to connect with people, and I like to tell stories,” she says. She describes that impulse as an inherently Indigenous way for her to approach being a musician.
Her musical foundation began at home. Riley’s grandfather introduced her to older country artists including Hank Williams and Patsy Cline. Her mother loved the country music of the 1980s and 1990s. The Calgary and Canmore folk festivals were part of her life from childhood and eventually became markers of the career she hoped to build.
Calgary singer-songwriter Jaiden Riley is nominated for three 2026 YYC Music Awards, including Indigenous Artist, Solo Artist and Emerging Artist.
Drawing from country, folk and bluegrass, Riley centres storytelling, community and her Indigenous identity in a career that has grown rapidly following her Ranchman’s Country 105 Rising Star win.
Her first real doorway into Calgary’s professional music community arrived somewhere…somewhat glamorous to the West: The Keg.
Riley was working there when musician Matt Blais walked in carrying a Taylor guitar. She recognized the instrument and struck up a conversation.
A few weeks later, Blais invited her to split a show with him at Hayden Block.
Riley laughs now at how little she knew. She arrived with two guitars in one key and no cables.
Blais became an early mentor, teaching her some of the things musicians are rarely taught formally: how to show up professionally, what works onstage, what does not and how to build a stronger live show. Last year, he brought Riley to the YYC Music Awards as his guest. It was her first time attending.
This year, Riley has three nominations of her own. Her win at Ranchman’s Country 105 Rising Star became another dividing line. Riley talks about a “pre-Rising Star” and “post-Rising Star” version of her career. Not because she believes she became a different artist, but because opportunities accelerated after the win.
“I still love her, and I still am her,” she says of the artist she was before.
The growth of the Jaiden Riley project also meant the growth of The Crybabies, the musicians who surround her onstage. Riley has a fairly straightforward hiring philosophy.
“You gotta be a nice, good person,” she says.
Then there is the musical requirement. “You gotta be better than me.” She laughs, but she means it.
“Everyone in the band is better than me, and that’s how it should be.”
The Crybabies emerged through relationships rather than auditions. Banjo player Brett Cassidy was one of the earliest musicians Riley performed with regularly. Guitarist Tory Rosso came into her orbit socially. Fiddle player Talia Aleksiuk approached her at a show and introduced herself.
“We all really just love each other, and we love music, and we love spending time together,” Riley says. That community has mattered particularly over the past year.
Riley’s mother died shortly after seeing her win Rising Star. She had been one of the most consistent people in Riley’s musical life. Front row at shows, knowing the songs and believing in the career before much of the industry knew who Riley was. Riley remembers calling her after the Rising Star win. Her mother told her, “I didn’t doubt it for a moment.”
The YYC Music Awards nominations came after her death. “It was a lot of joy and so much gratitude,” Riley says. “But also, I really wanted to phone her and tell her, and I couldn’t.”
The loss has existed alongside one of the busiest stretches of Riley’s career. She estimates she played roughly 45 shows between mid-June and mid-August. Music has helped, as have her partner, friends, bandmates, prayer, smudging and Indigenous ceremony.
One of those performances was the Canmore Folk Music Festival warm-up, a stage connected to a dream Riley had identified years earlier. It was also only her second performance after her mother died. Her first had been difficult enough that Riley wondered whether she could continue performing.
Canmore helped answer that question. Now she is looking toward recording. Despite the scale of some of her opportunities, Riley currently has one officially released single, “Chickens in the Trailer Park”, while sitting on enough original material for what she estimates could be two albums.
She does not want to make an EP simply because it is convenient. She wants a record, on vinyl. Despite the nominations, Riley is clear that an award show does not change the reason she does this. “If I’m performing at the YYC Music Awards, or if I’m performing in the corner of a bar,” she says, “my why remains.”
Bijaan and Riley sound nothing alike. Their careers have travelled very different roads. What connects them is what sits underneath the recognition: childhood friendships, mentors, collaborators, family histories, small stages, grief and years spent building before the wider industry had a reason to notice.
The 2026 YYC Music Awards take place September 20 at the Event Centre at Grey Eagle Resort & Casino.