Keysha Freshh’s cheeky album title, Pretty Boys Break My Heart, sounds primed to be the next hashtag or meme-able phrase splashed over the Insta stories of Millennial and Gen Z influencers.
The new album – which drops Aug. 16, 2024 – is just the latest step in a rich career. Born in Toronto, Freshh had her first song, “Summer’s Coming,” published when she was just five years old. By 16, she was working with Doug E Fresh on her song, “’Hollywood Fresh.” She was collaborating with legends, signed to an indie label, and hanging in New York City. In 2016, she became one-quarter of the feminist hip-hop collective The Sorority (from whence came the later solo careers of Freshh, Lex Leosis, pHoenix Pagliacci, and 2019 Polaris Prize winner Haviah Mighty). After The Sorority disbanded, Freshh contributed to Nike’s 2019 official Women’s World Cup Anthem.
Pretty Boys offers her usual bold authenticity, poetic storytelling, dynamic flow, and thought-provoking lyrics. As noted, it’s meme-able, but behind the catchiness lies a plethora of heartbreak: the tragic death of her best friend, the dissolution of relationships, and the end of love affairs. Far too much pain, at too young an age, says Freshh (born Keisha Fanfair). She hopes that listeners can connect with the album, but not necessarily relate to its painful subject matter.
Select the image to play the YouTube video “The Story of Keysha Freshh”
“When I think about when this album’s creation started, I say it started the first time I fell in love, at 14,” says Freshh, who concedes that in many ways, she’s been writing it for well over a decade. “What I really want to come across is that heartbreak is not a linear thing. It’s not just dating: ‘My partner broke my heart.’ Heartbreak comes from losing people, friendships ending, business relationships going sour, not getting that promotion, your children. But you learn from it, you grow from it.
“This album is really me reclaiming my heart. Me finding love in me. Finding love in life, and not relying on people or situations for that happiness,” she says.
Freshh decided to take the lead on all the songs, while male artists – such as R&B legend Ray Robinson, Vonne, VII, Tona, and her cousin Maestro Fresh Wes – sing the hooks, subverting hip-hop’s tendency to use female vocalists as track accessories for male-dominated records.
“I’m not one of those artists who’ll put out an album every year, or two albums a year. I don’t oversaturate my brand of music. Everything is very intentional,” says Freshh. “So, when I decided to work on this album, and start preparing for it, I was, like, what do I want to convey?” explains Freshh, who says that placing her voice in the forefront, as males hold down the backups, is as much about regaining her female voice as her artistic one.
Freshh wrote the album over a year-and-a-half, and describes recording sessions where the studio was a flurry of activity: Robinson freestyling, scatting; Vonne practicing his lyrics; VII putting his words to paper; others contributing their work. The end result is exactly what she intended.
“I’m rapping on all the verses and then I have Ray Robinson [on] the interlude,” she says. “I have VII, he’s singing a hook. Vonne, he’s singing a hook. Even Maestro Fresh Wes! People are going to be really impressed that Maestro is singing the hook on our song.”
Now, Freshh is ready to take the album to the people. “This was created from me, for them,” she says. “I’m really excited to perform this album… to share this vulnerable side of me on a big stage.”