Smiley Reflects on Viral Bars, Working with Drake, and Don’t Box Me In | The Sit Down' Ep. 56
Hosted by: Jess | Video: Keemya Parsa | Photo: Kianna S | Producer: Alex Henein | Location: National
On the 56th episode of The Sit Down, hosted by Jess, Toronto’s own Smiley joins THHGURU for a conversation that cuts deeper than music. Known for his unfiltered flow and off-kilter delivery, Smiley has carved out a lane that’s uniquely his — blending raw life experience with signature energy and a voice that refuses to be ignored.
In this exclusive interview, Smiley opens up about the meaning behind his new album Don’t Box Me In, and how it represents more than a title — it’s a personal mantra. He breaks down tracks like “Mazza” and “Spill the Tea,” giving fans a closer look at the mindset behind the music.
Smiley also reflects on his collaboration with Drake, the moment his “Prada and Gucci don’t go together” lyric went viral, and why he approaches songs differently depending on the artist. Beyond the bars, he talks about what success looks like today, how fatherhood has shifted his perspective, and why he still feels like a voice for Toronto’s underground.
From viral moments to real-life reflections, this is Smiley at his most open.
