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What does it really take to be a legend? The discussion around being the best will always be subjective, but the brand of legend is something that can be standardized to a degree. Things like longevity, impact, consistency are obvious relevant key performance indicators (KPIs), but what about things like reverence for the culture? It’s a question that must roll around in the back of the mind of 26-year-old Keisha Raisa Fanfair, better known as Keysha Freshh, at this point in her career. And not prematurely by any means.

After having her first song published at five years old and performing her first written rap as a member of the Toronto Children Concert Choir at 12, Keysha has released a total of 10 projects. Eight solo. A collaboration project with experimental Toronto hip-hop group Pearls and Bones called All the Wrong Places. And, of course, The Pledge album along with Polaris Prize winner Haviah Mighty and Lex Leosis – her counterparts in Canadian supergroup The Sorority, which just announced its upcoming tour will also be its final.

While Keysha always had a knack for performance and song writing, things didn’t get serious until 2008, when an MSN chat with Grammy-award-winning producer T-Minus pointed her in the right direction. Soon after, she found herself rubbing shoulders with the likes of legendary beatboxer and hip-hop pioneer Doug E. Fresh and took off to the Big Apple to kickstart her journey. Keysha locked down some early wins. Shooting her first music video “Hollywood Fresh” at the Empire State Building — a first for an artist since 9/11. Becoming one of the youngest rappers to have three songs in rotation on Canadian radio. Sharing stages with legends like Wu-Tang and Snoop Dogg. All while building real, organic and genuine relationships with industry insiders and artists that have remained no more than a phone call away for years. A perfect example of this is how she ended up collaborating with producer Deion Bala on her latest release Field Trip. More on that later.

When you start adding it up, the numbers don’t lie. Over 20 years in music, accolades from her peers, a reverence for the culture (a rare quality in today’s artists) and arguably at a point where her career is in its sharpest incline, Keysha has a lot she could rightfully boast about. However, accomplishments aren’t likely to be the topic of natural conversation with her. She’s more likely to school you on the correct way to package your shoes for flights (cold luggage compartment air causes condensation). Or pass on a piece of wisdom imparted on her by some of her famous family (she counts Canadian hip-hop icon Maestro Fresh Wes and legendary Canadian DJ Mel Boogie as cousins and celebrated Canadian journalist Ron Fanfair is her father). Or maybe get really deep into breaking down a line from some obscure rap song. On paper, Keysha has checked many of those boxes towards greatness and after so long in the game it’s almost frightening to think of what she’ll accomplish next. With what could already be considered a storied career, maybe legendary status isn’t what she’s chasing. In fact, looking back, she says she’s only now getting a chance to appreciate it all.

Sounds just like what a legend would say.

With all the success of The Sorority, what was it like to go back to a solo focus?

It was actually difficult transitioning back into just solo stuff. Even with this being my eighth project. Touring with The Sorority and stuff it was a little difficult at first. When you’re used to being in a group, you’re only writing one verse. Now you’re like, ‘I got a whole song to myself!’ It was great, it was fun. At one point it started to feel like home. I was really hands-on with the process for this particular album. It wasn’t an easy transition at first and there was a lot of times I would hear a beat and (think) this could be a dope Sorority song. It’s that push and pull now.

“Calls” falls into that familiar vibe of previous tracks you’ve released like “Lala” and “Rewind/Undo”. There’s a sound there…

“Calls” was special because I knew going into that album, I wanted Leila (Dey) on it. I didn’t know on what because I didn’t have anything. “Calls” is a beat I co-produced. That’s my first production because I crafted it for her voice. I wrote the song, everything, for her. When she came on board and did it, I remember like crying in the studio because this was my vision. I thanked her so much. She asked me to stop. She’s one of my favourite artists. People can’t believe how amazing the record is and they are resonating with the words and it feels good because I wrote it.

“Hero” is a standout. Why that record as the single?

It was weird because if you ask someone what song I should put out first they would say “Calls” of course. That would be the single. In my head, if I was just listening to the album, I would say why the heck wasn’t “Calls” your single? I didn’t want it to be. I wanted people to hear that song and say, ‘wait a minute.’ “Hero” was important because I wanted people to hear me rap. On Pledge there was more sing-song kind of vibey records, and I wanted y’all to hear me rap again. I was always a rapper that spit heavy, heavy, heavy bars. I wanted to give them a full two minutes and 33 seconds of bars. Back to back to back. Starting it off with “First thing’s first, rest in peace Nip / You know I had to say it / My n***a died a martyr / So f**k being complacent.” That to me hit. When I wrote the line. When I heard it back. After that my engineer was like, ‘Oh you’re rapping today!’ I just felt like I wanted to get that out there first. It just spoke to me.

Women… we’ve fought for places in hip-hop to even have a voice.

You got interested in producer Deion Bala’s work through a sneaker unboxing video. Tell me about that.

Everyone knows I’m a big sneaker head. I was just chilling, watching some unboxing videos and this one video had this beat in the background. I had to find out what beat is that? I commented on the video and the dude replied, ‘it’s my homie Deion Bala.’ He just gave me that name. No Instagram or nothing. I wrote the name down and left it in my phone. Then, two weeks later I saw this person liked two of my pictures and his Instagram name was Deion Bala. I go in my phone and I’m like, ‘yo, it’s the guy!’ I hit him up. I jumped in his DM, and we still laugh about it because I have the message to this day. I told him it was so ironic that I was looking at a YouTube video that had your song. The YouTube video host didn’t connect us. Deion just ended up liking my picture. My YouTube name isn’t just “Keysha Fresh” so it was just random. The YouTube guy didn’t happen to know I’m a rapper. And they’re both from Toronto. Deion sent me a beat pack with the beat from the video. This was 2017 … Then around August 2018 I decided to work on a project with him. We brought Deion into the studio and it was his first time in that environment. He was shocked. He couldn’t believe someone was doing a project with his beats. I had a lot of input on the production and we were able to create a really great project.

Do you usually have a chance to be in the studio with the producer?

No, it’s usually emailing stems. To have Deion in the studio was different. There were so many advantages to having Deion in the studio. He’s there tweaking and working on his production. He’ll get inspired and add something. We’re building songs, not just recording. That whole process was different and that’s why the energy for Field Trip is different from all my other albums. The process for this album was building songs from scratch.

So, on the topic of you being a sneaker head, you did some cool work with a footwear company not too long ago. Nike. How did that come around and what was that experience like?

Nike was… it was… how can I even put it in words? We prayed for that. The Sorority, we always were happy doing all these big things. Billboards and all kinds of stuff, but we’ve never had a brand come knock on our door. We see all these artists in the city getting all these sponsorships. We were patient and we understood that everything has its time, so we just kept working. We got an opportunity through an agency to submit music for the women’s World Cup. They really thought we would do great, so they sent us a link to submit. We were praying. Then, our manager hit the group chat and said, ‘Guess what?’ and he responded with all these weird emojis. Then he finally told us, ‘Nike wants you guys!’

I called my mom and I was crying. This is my favourite footwear brand, my favourite streetwear brand. This is Nike! It was a collaboration between Nike, Canada Sports and Team Canada for the women’s World Cup and we made a chant/cheer for the World Cup anthem. We were a part of the campaign with some other influencers. They sent us a Nike suitcase with clothes and hats and socks, everything. We were just so grateful for the opportunity. We met a lot of cool people. A lot of people from Nike, a lot of people from Canada Sports. It was such a cool opportunity to be in that environment. That was like a bucket list check.

With how far you’ve come, all the accolades, sharing stages with legends, does anything surprise you anymore? Do they even feel like achievements?

At this point everything surprises us. Technically, by the laws of the land, we’re not supposed to be here. Women… we’ve fought for places in hip-hop to even have a voice. The fact that we now get that voice, but also the opportunities that come along, it’s always a shock. It’s always a blessing. When we performed at the show with Wu-Tang, Snoop and K’Naan, to find out we’re all sharing the common spaces and our trailers are all linked, we all geeked. Everything is a blessing and none of us take any of it for granted.

Did you get a chance to connect with any of them?

We hung out in Snoop’s trailer. Really cool guy, really cool family and friends around him as well. That was a lesson for me. I’ve always kept my circle close. It’s always been family and friends. With Snoop, you were seeing him with people you know were his boys from back then. The people that were around weren’t just entourage, they were friends forever. It was a good lesson to see. Who you keep around you is important. That’s why you never hear Snoop in much scandals. Those lessons you just observe and learn.

We got to hang out with some of the Wu-Tang members. That was pretty cool. I was able to tell Genius that he was the reason that I love chess and that he made it cool to like chess as a Black kid. I was able to tell Ghostface, ‘you combined hip-hop and Marvel, two of my favourite things, I became a Tony Stark fan because you and hip-hop told me it was cool.’

What’s the next evolution?

Earlier this year I started my own social media, marketing and brand activation company. House of Rasia. We do pop-up brand activations and social media branding. My first client was the Association of Black Law Enforcers. I did their social media for their event and some of the branding leading up to it.

What brought that about?

My uncle owns a restaurant called Windies. I told him he would flourish if he had social media content. I started giving him ideas of how to make the brand better and then people were willing to hire me just to give them consultations in that direction. My cousin has a construction business in Atlanta that he wants me to help him with. I like doing it. So, I’m just starting it up and figuring out different markets and how different social media (platforms) work. We had our soft launch and got a client. I did the work and was happy with my results and now that I have stuff to show, I’m going to keep going.

Photos © Isa Miguel Ransome + Urbanology Magazine

During Battle of the Beat Makers 2018, Grammy-award winning producer !llmind sat down to talk falling in love with producing, navigating the music business and why, despite all his accomplishments, he still tells himself daily that he ‘ain’t shit.’