Mississauga-based rapper AR Paisley has been on the rise since he first started freestyling and battling back in high school. Since then, Paisley has worked to garner respect from his fans for his honest and relatable music, mastery of freestyle, and gifted lyricism.
Some of his musical influences include Ludacris and 50 Cent, as well as the late Tupac Shakur and Biggie Smalls. He dropped his debut album Timeless in 2019, which allowed fans to appreciate the 90s and early 2000s influence in his music.
Paisley has continued to be active, dropping several singles, EP’s, collabs, and projects since. AR has a total of 8,000,000+ streams across all popular platforms, and has solidified himself as an artist to appreciate in the Toronto music scene.
His “Car Freestyle” series on Instagram have an intimate, candid vibe that many artist struggle to create. Because of this, AR’s fans have grown to celebrate his realness and allow him to stand out as a real, unfiltered talent. His widely recognized singles “Cost Ya” and “Life’s Too Short” have proven his ability to connect with the masses, turning fans of freestyles, into fans of his music.
In an exclusive interview with Sidedoor, AR Paisley delves into his creative process, journey as an artist, and his plans for the future.
Tell me about yourself. How did you get into rap?
I just started in high school, but I didn’t really take it seriously – rapping was just something to pass the time. It tuned into rap battles around the city, and I started taking it serious in 2017. I dropped out of high school and was going through it; music was an outlet for me. That year, I made my first project, which was about 8-10 songs, and I just went crazy and had fun at the studio. That project got some reception, and that’s when I decided I wanted to really focus on music.
How has Toronto/Sauga culture influenced your music?
I think it’s definitely been inspirational in the last couple years, with so many artists from the GTA breaking out and becoming mainstream. That just shows underground artists that it’s possible to make it out of the city, that it’s possible to live out the dream. These are people from my city who went to the same stores as me. There are times you as an artist feel like you should stop, but seeing this just pushes me to keep going.
I’ve heard some of your popular freestyles like the one inspired by “Love Yourz”, which feel authentic but still similar to the original song. What’s your process like for freestyling?
When I first started gaining traction, it was from my freestyling. I would just put on a beat and go off, and people seeing me rap in person was when they’d get the most hype. Some artists are good at melodies or beats, but my strongest suit is being able to rap and freestyle.
With Love Yourz, it was a car freestyle and I just got my boy to record it. That was a turning point in my career, because it showed me what I was best at – making music that makes people feel something. Saying something real. I was kind of torn between two sounds, the style of Love Yourz and a grungy hip hop style that was different. Putting this freestyle out there and seeing thousands of people sending it to their friends, commenting and reaching out showed me what sound I should choose. Real music like that is going to get an artist real fans that support you and feel your music.
After hearing “Life’s too Short”, I think a lot of people realized you’re a storyteller. Are there specific stories you find important or want to delve into in your music?
Before I was even serious about music, writing was just an outlet for me to forget about everything that was going on. Usually when I’m writing, I just go with the flow. I had a lot on my mind with “Life’s too Short” and I was just thinking about what was happening around me. I do think I’m a storyteller, but it just comes from what inspires me. But I’ve been at points in my career where I don’t feel inspired, and that’s when it gets hard.
How do you deal with writer’s block or lack of inspiration?
The main thing for me is just trying to experience new things. I feel like inspiration is all subconscious, because there are have been times when meeting someone inspired a song, when I wasn’t expecting it to happen. It’s also happens when I go on vacation and come back; suddenly I’m ready to start writing or working again. I try and meet new people, talk to new people, or go to new places.
Who are your biggest musical inspirations?
I really like listening to old music and old rap. This year, I went back and listened to a lot of Eminem, and I started diving back into “Stan.” I basically listened to all the rap songs that have won Grammy’s because that’s a huge dream of mine – and I realized the songs that win those awards are all storytelling songs. They connect with people on a deeper level, and they actually address real things. There’s a ceiling a lot of rappers hit and they don’t pass it, but the rappers that get past that and win awards have built fan bases because they’re vulnerable and real.
That’s so true – so many of the rappers that make it are noticed because of their vulnerability. What’s next for you? What can fans look forward to?
The plan for the next couple months is to start Paisley Sundays – where I’m going to try and drop a song every Sunday or every other Sunday. I feel like this will be exciting for fans and it’ll also be exciting for me to drop a song a week, so that’ll be posted on my Instagram soon.
Be sure to show love to AR and the Paisley team! He doesn’t do a lot of interviews, probably because his music speaks for itself, but he’s still got a lot to say. Check out “Life’s Too Short” above and stream his Paisley Worldwide project now!