Keysha Freshh: “Checking Into the Heartbreak Hotel”

For Keysha Freshh and her new album, it’s like a Canadian hip-hop carnival. The Toronto-area rap artist has just released her new album, Pretty Boys Break My Heart, featuring the single “905.” For any Toronto area resident, the title “905” is sure to resonate, a reference to the area code associated with many of the peripheral cities in the area. The song is a nod to what they refer to as the Greater Toronto Area. Featuring her stellar storytelling abilities, it touches on the realities of urban life growing up in the area.

There’s a lot of anticipation surrounding the release of Keysha’s new album. It’s been a six-year hiatus, but she is back doing what she does best. Keysha has been rapping since the age of 11 and since then has released eleven solo projects. Her latest project, Pretty Boys Break My Heart, features her as her most focused and self-assured. The album features some very special guest stars. It’s a who’s who list of acclaimed Canadian hip-hop and R&B artists. The list is headlined by Canadian hip-hop pioneer Maestro Fresh Wes, Ray Robinson, and Tona. Despite the notoriety she has created for herself, Keysha remains committed to her Toronto area roots which helped make her into the artist she is.

Joining us today for a special Guest Blog is Keysha Freshh. She gets very personal discussing Pretty Boys Break My Heart, its roots, and its inspirations, particularly heartbreak.

“Can’t catch keys with the okie doke
I play my position
And I’m quiet
But trust me I see through the smoke”
– “Rockabye Baby” feat. Maestro Fresh Wes

I think that bar pretty much summarizes how I’m feeling these days.

Creating this album felt like therapy, in a way that I didn’t know could exist. This album, truly, has been in creation since the first time I fell in love if you really think about it. It’s a cumulation of moments that have shaped who I am today as a partner and as a person.

When I was 14, I fell in love. I used to see this guy everywhere around the neighbourhood. And I thought he was super good-looking. I knew his cousins pretty well, so one summer day, I went to his cousin’s house and he was there. I thought to myself, I can’t leave without exchanging numbers. We were outside and I was about to leave, when he said, ‘We should hang out this summer,’ I agreed.

Before I walked off I said, ‘I’ll give you a call tomorrow and we could link up’ and then I walked away, all in one intentional motion. He smiled and nodded, and then his face got serious, he yelled out behind me, ‘Wait, how are you gonna call me? You don’t have my number!’ I smirked, already with my phone out, turned around, and we both started laughing. He knew, in that moment, he got a dope one in me. We dated for four years, my high school sweetheart.

Keysha Freshh, photo by Brice Zhao

When I was in elementary school, I was in French immersion. I met this kid who was tall, funny, and sucked at basketball, but we still let him play because he was older and he was tall; we just told him to grab the rebounds. In grade 5, I left that school and went to a different school not far. In eighth grade, I reconnected with him, he ended up coming to a party I was playing music at for my friend’s birthday. We became inseparable, and he truly became a brother to me. We shared a friend group from grade eight to today.

Both of these two young men, Nicholi Antony Dyce and Khalid Chrysostom, passed away a little shy of three years apart. Nicholi September 7th, 2013 and Khalid June 27th, 2016.

Heartbreak isn’t as linear as the fictional novels, and the Hollywood writers make it seem. It’s not always two lovers, going through a bad breakup, or someone cheating on someone else. Heartbreak looks like losing a family member, losing a best friend or earth-shattering, life-changing, events.

The themes of this album explore heartbreak in many ways, traditionally and unconventionally. Losing my best friend, my high school sweetheart, breakups, makeups, feeling isolated by the culture I’ve given so much to, everything in between.

I’ve compiled an all-star cast of some of my favourite artists in the country. Tona and I go back-to-back on a song that feels like a psalm called ‘Cathedral.’ Jelly TooFly and I engage in suspicion that we are two of the few women in hip hop in the city keeping it true to the culture on ‘Pins and Needles.’ And my long-awaited collaboration with the Godfather of Canadian hip hop; Maestro Fresh Wes, where he takes on the role of mentor on ‘Rockabye Baby.’

There is a song on Pretty Boys Break My Heart for everyone, every mood, and every heartbreak.

I hope you enjoy it, but oddly, I hope you don’t relate. Heartbreak sucks.”

Keysha Freshh “905” single artwork