Canadian rap upstart Tinywiings delivers debut ‘Pretty Problems’ EP via Sony & ShowOffGang Music

The roster at ShowOff Gang Music continues to grow as the Pittsburgh-bred imprint welcomes their first-lady Tinywiings with the release of her new project Pretty Problems.

Along with her recent “Wind Me Up” collaboration with J-HAZE, the five-track EP also finds Tinywiings joining forces with 86LOVE for their club-ready anthem “Pop Sum.” 

Tinywiings F. J-HAZE “Wind Me Up” Music Video

Overall, the short and sweet extended play release boasts an impressive element of versatility. With a sense of unwavering confidence and defiant swagger, Tinywiings navigates a roundabout of production pockets. Her prowess is hard to ignore as she meanders between beats reminiscent of old-school Memphis horror core Hip-Hop, R&B ballads and gritty boom-bap punch-in records back-to-back.

Tinywiings latest EP marks dawning of Sony & ShowOffGang Music-Backed Era

Believe it or not, this EP is the culmination of six years of hard work for Tinywiings, who hails from Canada. While the news of her joint-venture deal with ShowOffGang Music and Sony has the streets buzzing, she had already previously managed to build an impressive discography whilst also cultivating a unique and alluring online presence.

”I started rapping only like six years ago now, but I started writing poetry when I was really young,” Tinywiings said in her recent interview with Da Matrix Studio. “So that’s kind of where it came from. And my oldest brother, he is a rapper and he’s the one who kind of got me into putting poetry over beats and how to structure a song.”

And with all that said, this year still may be her best yet. Tinywiings has kicked up an undeniable amount of dust while trailblazing on her own methodical 2026 campaign, landing on major editorial playlists such as Apple Music’s New Music Daily, Rap Heavy Hitters and The New Toronto. She’s also served up several viral in-studio performances including her electric rendition of her Pretty Problems EP track “My Price” for Big Fendi’s The Come Up curated series.

”I feel like that’s when I can actually be Tinywiings, and just be hype and let the adrenaline flow,” she said when speaking about her love for performing. 

Heavy ShowOffGang Music Activity Maintains Throughout 2026

On the other hand, the record also serves as somewhat of a fourth quarter blitz for ShowoffGang Music-architect J-HAZE, who started this year off blazing out the gates with he and BhramaBull’s The Maineline 2 collaborative project back in January. 

Prior to he and BhramaBull’s recent joint-effort, J-HAZE last delivered his solo 10-track No Tomorrow album last year in May.

Check out Tinywiings’ Pretty Problems EP below.

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