88 Days of Fortune collectively changed Toronto hip-hop. Has its luck run out?

On a cold December night back in 2009, a friend invited me at the last minute to a hip-hop show. I remember pausing in the doorway as I surveyed the packed and sweaty room. Most of the performance-based hip-hop shows I had attended in Toronto drew a predominantly male crowd who invariably stood in one spot for most of the night, drink in hand, exhibiting practiced head nods.

I want to be able to expand what a genre is supposed to mean.- Ayo Leilani a.k.a. Witch Prophet

But this was something else. The room was filled with men, women and gender-queer individuals. The performers had glow in the dark face paint. The head nods had been replaced with jumping, grinding and unapologetic excitement. I had stumbled for the first time onto a show by 88 Days of Fortune, an artistic collective that shook up the underground music scene of Toronto with their alternative sounds, styles and visions of what hip-hop could be.

I spoke with 88 Days of Fortune co-founder and co-director Ayo Leilani a.ka. Witch Prophet about an artistic movement whose name was attributed to an online psychic's prophecy that Leilani would have 88 days filled with fortune.  

"It's like a weird, hidden legacy," she says. "It was like a record label where everyone was sort of developing their artistry for six years. When you really think about everybody who was in 88 Days, and where they are now, a lot of the [Toronto music] scene is 88 Days. They're making it, but the problem is a lot of people now who are hip to a KJ [Keita Juma] or Brendan [Philip] or bizZarh have no idea about 88 Days."

Initially formed as a group who wanted to organize a mini-city wide tour, 88 Days of Fortune was a collective made up of artists in music, photography, fashion, tattoo art, graphic design, film and theatre. It soon evolved into a monthly showcase, PR company and unofficial record label.

Sharing a common desire to push beyond genre and medium, these artists created a sound that lived at the intersections of punk, trap, rap, electronic music and neo-soul. They carved out an alternative space of creativity with futuristic aesthetics in their content, presentation and performance styles that reimagined what urban/hip-hop culture could look and sound like.

"Everybody in 88 Days was on the same wavelength. We would be sitting around and talking about magic and talismans and the power of words." Leilani says the members asked themselves questions like, "How do we shift our dimension? How do we make this happen for us? It was recognizing our power as people, our actual physical power and trying to make it a real, tangible thing. Those kinds of conversations went down, and it really expanded everybody's minds. I think that was one of the strongest things that made us different from all the other crews."

Beyond pushing hip-hop aesthetically, 88 Days of Culture also curated spaces that were unapologetically political in their inclusion and celebration of queer culture. "I don't remember any hip-hop parties where it was queer friendly at all until 88 Days. In terms of that legacy, in terms of integration in the scenes and specifically the hip-hop scene integrating queer and straight people together, that legacy is 88 Days."

They quickly realized that the spaces they were organically curating were also appealing to funders looking for projects that checked all of their equity boxes. As that support helped to expand their reach, articles in NOW Magazine, Exclaim! and the Toronto Star promoted and reviewed their shows, proclaiming 88 Days as the next big thing. The venues got bigger as they were invited to host events at the Art Gallery of Ontario and Artscape's Gibraltar Point. They embarked on a four-country European tour in 2012 and, at each showcase — which now frequently featured exhibits and theatrical performances — their audiences grew larger. For a moment, it felt like everyone was trying to jump on the 88 Days of Fortune bandwagon.

But despite the hype, there were rarely enough tangible resources to adequately sustain the artists, or the co-ordinators. Following the trajectory of many artists and organizers before her, Leilani says she frequently went without pay, choosing to allocate the funding in a way that ensured everyone else received something. (That something was generally quite small.)  Although admirable, this strategy is rarely a sustainable one. For years, Leilani balanced jobs in coffee shops and her individual artistic dreams as a singer and songwriter with her vision for 88 Days of Fortune.

Although successful in sparking a buzz, there was limited infrastructure to facilitate their next steps. "The journalists or whoever it is that create the culture in the city, love to big up emerging hip-hop but they don't follow through with it."

Leilani compares the Canadian music industry's treatment of hip-hop to high school. "You could be in grade 9 and be number one in grade 9 but have people in 12th grade not know who the hell you are. That's kind of what it's like.

"You spend all these years building up, [passing] each grade to get to where you are, only to get to the 12th grade — but still not graduate. The Canadian music scene is like, you will forever be in this high-school cycle of small-pawn success.

"I want to be able to have my music have just as much publicity that an indie rock group would have," she adds pointedly.

It was in part this realization that led many members of 88 Days to eventually move away from the collective and begin focusing their energies on their individual careers, attempting to break through the glass ceiling that so many artists find themselves trapped under.

"In terms of the collective, there definitely was a beginning, middle and end. If we were in high school, this would be our graduation. Now it's a career, so we have to actually focus on our own careers instead of always being together, doing this thing."

Changing her stage name from Ayo Leilani to Witch Prophet has signified a new chapter for Leilani as an artist, shifting away from what felt like limiting assumptions of her role as a neo-soul singer. "It's a more experimental sound. It allows me to do what I want to do. I want to be able to expand what a genre is supposed to mean."

This doesn't mean the end of 88 Days of Fortune. Leilani has dreams for the business side evolving into an actual record label and/or music festival. The collective continues to help artists finance music videos, and her group Above Top Secret is releasing their album partly through 88 Days along with another label. 

Late last year, 88 Days released a sixth anniversary mixtape titled They Live, and they have plans for other projects in 2016.

"I don't want to let it go. And I also believe that that's happened way too many times with hip-hop-centred collectives in Toronto. It's this amazing thing, it's here and then all of a sudden it fizzles out. It doesn't allow for anything new to be built on top of it. If we're constantly building from the bottom for our hip-hop scene, then it's never gonna be as strong as the other scenes that are happening in Toronto.

"The number 8, if you turn it on its side, is infinity. So we used to say, it's double infinity days of fortune. Which I still believe."

Val-Inc. with Witch Prophet, MO:delic. Sat., Feb. 20. The Music Gallery, 197 John St., Toronto. 8pm. $15; $13 advance; $10 members. Witch Prophet, Amanda Parris, Val-Inc.and Garvia Bailey will speak on a panel moderated by Alanna Stuart entitled: The New Black: Challenging Musical Tropes. 5pm. Free.

Past and present members of 88 Days of Fortune:
Ayo Leilani a.k.a. Witch Prophet, Francesca Nocera (SunSun), Keita Juma (KJ), Brendan Philip, Yannick Anton, Nadine Stillman, Wolf J McFarlane, Spek Won, The OBGM's, AKOKO, Maiko Watson, Amenta, Bahia Watson, MFP, THEESatisfaction, Bizzarh, Jah Grey, Tee Fergus, Deon Mars, T.Ana Cole, Jamilah Malika, Fro Casso, Latasha Alcindor and Yasmine.