Connect with us
Book confidently and save this Halloween! Enter promo code HALLO25 for up to C$25 off our fees on flights and other travel deals.
Black and white photo of Drew Carrymore by Charles Graham
Drew Carrymore (Photo: Charles Graham)

Interview: Q&A

Drew Carrymore talks music; bringing creativity & lifestyle to HipHopCanada

Since roughly 2010-2011, Toronto-based Drew Carrymore has been heavily involved with Canadian hip-hop. He started out as a rapper, and is now behind the scenes focusing on creative direction and other ways to lend his support to homegrown creativity.

“Musicians are like superheroes to me, they all have different superpowers.” – Drew Carrymore

Drew quickly became a mainstay in the Toronto scene, and put years of hard work into building up his music career. He’s released two projects in total, including his most popular mixtape Drew Carrymore’s Day Off, and has been featured on several projects by other artists. In 2012, Drew appeared alongside Thwaglord and OVO’s OB O’Brien on the song “2 Red Cups” by Boogz Boogetz. Boogz included the track on his project, C.O.O.L.

Drew, 29, has built up an impressive resume, and earned the respect from his peers in Toronto, but sometime around November 2016 decided to switch his focus to working behind the scenes. On Nov. 3, 2016, Drew posted his first film-based pics on his Instagram profile, featuring Toronto’s Cans and Baka Not Nice in a series of club shots. Today, he’s got over 200 posts on that profile and his involvement with promoting local talent has grown substantially.

“Expect left field stuff. Starting with creatives and behind the scene people; photographers, producers, management, etc. Different people involved in making stuff happen that don’t get as much light as they should […]”

A few weeks ago, Drew reached out and we began discussing the idea of him joining the HipHopCanada team, and bringing his creative fortitude to our platforms. Drew has a ton of exciting ideas that are certain to add value to the content we offer our viewers, and he’s eager for you to see them.

But before we get Drew in the mix—something that is long overdue—we wanted to get him in the hot seat so you can see what he’s all about, his passion for Canadian hip-hop, and to get a better sense of what to expect from his coverage.

You can find the Q&A with Drew below, and stay tuned for his regular coverage of the scene, coming soon!

Toronto-based Drew Carrymore talks music; bringing creativity and lifestyle to HipHopCanada

Drew Carrymore (Illustration: Demi Awe)

Q&A: Drew Carrymore

HipHopCanada: What’s your earliest memory of being a fan of hip-hop or just music in general?

Drew Carrymore: Aww man, umm… Colombia House is for sure one of them. Seeing all the album covers together in alphabetical order. Pretty much the same time I was learning how to read and write at school. Sounding out band names and bizarre album titles almost for practice. Another time, weird as it sounds, I would see Wu-Tang logos drawn everywhere at school. One day I came home, drew it in the carpet with my finger and asked my parents what it meant!

HipHopCanada: This interview is about you switching from making music to covering different creative stuff as well as music, but I still want to know which of your musical releases to date you are most proud of. And why?

DC: I think this one project I had called Drew Carrymore’s Day Off. It was a play on Ferris Bueller’s Day Off and ran like an old school mixtape right after that era was kinda ending. Someone literally the other day uploaded a bunch of the songs to SoundCloud and hit me up. I posted something on Facebook about it and people said they’re still playing it (Laughs). I listen back now like, “how’d I even come up with this stuff?!” We were having so much fun, talkin’ bare shit! Shout out Burly, man!

Drew Carrymore talks music; bringing creativity and lifestyle to HipHopCanada

Artwork for Drew Carrymore’s Day Off

HipHopCanada: What ultimately inspired the decision to hang up the mic and focus on behind the scenes music journalism / story telling?

DC: Random, but back in the day I had a shaved head and would show people my music. They’d be like, “ya it’s cool.” A few months later I’d show people the same music but with a curly, lil’ fro and some cooler clothes on. Their responses would be totally different! Guess what I’m trying to say is I looked more the part and realized it wasn’t all about the music. So to answer your question, probably just noticing how much time it takes to get it all right. Right in the sense of all the aspects of the behind the scenes stuff. I always took interest in all that and had my hand in it anyways, so why not try to see some of these next ideas out in different ways?

HipHopCanada: Do you see yourself putting out new music in the future or has that ship sailed?

DC: (Laughs) I think it has sailed but I’m a decent swimmer so maybe. I mean I hope so, eventually but it have to be super tight. I got some references though, I’d love to write! Shout out my guy Harry James, he really motivates me.

HipHopCanada: Is there a particular Canadian hip-hop project by someone else that you’re looking forward to in 2019?

DC: Swagger Rite! I’m not sure what it’s called, maybe “Hottest Out.” He brings the best energy everywhere he goes and everybody loves him. He’s a swagged out pedestrian!

HipHopCanada: What is the biggest advantage of being a rapper or hip-hop oriented music maker in Canada?

DC: Probably being able to get a fresh look cause everyone in the world looking at Toronto right now and wants to know somebody from here. And the Canadian music scene is full of knowledge and education. There’s some real decorated muhhfuggas out here with Grammys and all types of accomplishments.

HipHopCanada: On the flip side, what’s the biggest disadvantage?

DC: Not being able to travel would suck.

HipHopCanada: What’s the biggest change to the scene you’ve witnessed since first getting involved?

DC: I hope everyone agrees with me on this one. Definitely the dark, melodic singing stuff. I feel like some artists got really good at it and incorporated it properly. Others just didn’t do it right and gotta wait their turn til’ their style comes back around. It’s all full circle, so never count out anyone creatively. Kinda like fashion recycling itself or like shootin’ film is poppin’ right now, people hated that stuff when digital came out.

HipHopCanada: All-time favourite Canadian hip-hop Video?

DC: Woah! Hmm videos I got a few, not all hip-hop though. Hip-hop, probably Jellestone’s “Money Can’t Buy Me Happiness.” I remember getting mad happy as a kid when that video played on Much. That song was massive, it was like Canada’s “Gettin’ Jiggy With It.” Non hip-hop video, there was this crazy under-produced Sum 41 joint, forget the name. Had all these action figures, Tech Decks and Barbie’s moving around like the band! My neighbour at the time worked for Sum 41, he’d show us the videos and ask what we thought of them as kids. Drake’s “Started from the Bottom” was really dope too.

HipHopCanada: Which artists from your city do you rate the most right now?

DC: Fuck, I’m gonna forget somebody (Laughs). Peep my Instagram @DrewCarrymore. Everyone on my page I rock with and they all do music and creative stuff, mostly from Toronto.

HipHopCanada: If you had to predict five years into the future, which artists will be running the city? Names we’re already familiar with or will it be a new wave of artists we haven’t even met yet?

DC: Like I said up top, this creative shit goes full circle. People grind their whole life for something, someone drops on SoundCloud and blows up off it. That’s the fun of it. Musicians are like superheroes to me, they all have different superpowers. I predict it’ll be the same elite mandem with some new faces too.

HipHopCanada: As a member of the HipHopCanada team, what types of stories and coverage can our readers expect from you?

DC: First off, I wanna say thank you Dutch and HHC for lending space on your publication for all this. Expect left field stuff. Starting with creatives and behind the scene people; photographers, producers, management, etc. Different people involved in making stuff happen that don’t get as much light as they should, fashion, lifestyle, maybe some events too. Then move outward, back to the familiar faces and trend setters you guys see on the forefront. Just expect a bunch of cool stuff!

Toronto-based Drew Carrymore talks music; bringing creativity and lifestyle to HipHopCanada

Drew Carrymore (Photo: James Ellis)

You can follow @DrewCarrymore on Instagram.

Jesse founded in 1999 and is currently the organization's Co-President & Editor-in-Chief.

Song of the Day


Featured Playlist: Canadian Fresh

Newsletter Signup

Signup now to receive periodical updates from

Recent Features

More in Interview: Q&A

Sennheiser (Canada) Inc.