Chuggo’s Top 10 Pioneers of Canadian Hip Hop (That Aren’t White)

I caught up with self-proclaimed washed-up Battle Rapper, Men’s Work Boot reviewer, Prisoner Rights activist, Cranberries Super Fan, and Urban Music Historian, Chuggo Freeman, who gave me a history lesson about his favorite Canadian Hip Hop Heavyweights (who aren’t white) from 1987- 2000 B.D ( Before Drake ) in honor of Black History Month!

(Bonus, it’s actually 11.)

1989 - Maestro Fresh Wes - “Drop The Needle”

“In 1989 Maestro Fresh Wes dropped ‘Drop the Needle’. Originally confused to be a song encouraging heroin addicts to put down their syringes, this timeless classic put Toronto/Canadian rap on the map!”


1989 - Michie Mee & L.A. Luv - “Jamaican Funk Canadian Style”

“Michie Mee is a Canadian rapper and actress. Canada's first notable female MC, she is considered a national Hip Hop pioneer. In 1991 she brought that Jamaican/Caribbean flavour to Much Music, and the world, with the legendary track ‘Jamaican Funk’.”


1990 - Devon Martin - “Mr. Metro”

“In 1988 West Coast Heavy weights N.W.A. released their debut album ‘Straight Outta Compton’ with the controversial track titled ‘Fuck Tha Police’. Two years later in the year 1990, north of the American border, a young man name Devon Martin stuck it to the Toronto Police and their practices of systemic racism with this eye opening track ‘Mr. Metro’. Devon Martin, aka Devon, is a pioneer of Canadian Urban Music and will forever be part of its history!”


1990 - HDV (Jackie Jasper) - “Pimp of the Microphone”

Jacky Jasper, known internationally for his work with Kool Keith on projects like Dr. Doom, and Analog Brothers with Ice-T and Kut Master Kurt, got his start as one of the four fathers of Canada's early Hip Hop scene while performing as HDV, as well as for his 1990 single ‘Pimp of the Microphone’.”


1991 - Dream Warriors - “My Definition of a Boombastic Jazz Style”

“The Dream Warriors, a Hip Hop/Jazz duo from Toronto, Ontario comprised of King Lou and Capital Q were known for hits like ‘Ludi’ and ‘Wash Your Face In My Sink’. But they are best known for "My Definition of a Boombastic Jazz Style". The album's most successful single sampled Quincy Jones' ‘Soul Bossa Nova’, which was also used as the Austin Powers theme song ‘Groovy Baby - Yeah’.”


1992 - Ghetto Concept - “Still Too Much”

“REWIND back to 2001 Ghetto Concept, Maestro Fresh Wes, Kardinal, Red 1 (of The Rascalz) and your best friend Snow!!

‘This is the remix dat dat da dat dat da dat dat da da da.. This is the remix dat dat da dat dat da dat dat da da da.’ I’ve listened to this a hundred times this month.. It’s TOO MUCH!!”


1995 - Choclair - “Let’s Ride”

“It’s your boy Choclair with ‘Let’s Ride’! Halftime show at The ACC, Much Music, Radio, video games, this track was everywhere and is a Canadian Classic HANDS DOWN!!”


1997 - Jelleestone - “Money Part 1”

“Jelleestone says ‘money can’t buy me happiness’ and it also couldn’t buy The Beatles any love!! Another west side Etobicoke heavyweight, repping Rexdale since the 90’s. He’s collaborated with Dancehall superstar Elephant Man and Canadian pop sensation Nelly Furtado!! Even though Jelleestone begins with a ‘J’, for as long as I can remember the streets have said he keeps it ‘G’.”


1997 - Rascalz - “Top of the World”

“I remember hearing once that the secret to making a hit song is to use a women's name or the name of a city or country! In the late 90's another secret to a hit track was to get Barrington Levy to sing on the chorus! (It worked for Puff Daddy & Shyne!) So when the Rascalz got Barrington Levy, Mr. Ding Ding Ding Doe to jump on their 1999 super hit "Top Of The World" where he shouted out NYC, Vancouver, Japan, Paris, Africa and the West Indies, Urban Music History was made...”


1999 - Point Blank - “Born and Raised in the Ghetto”

“This is my favourite Canadian Hip Hop/ Rap group. These dudes have tons of bangers that are not videos, as well .. ‘These Criminals’ and ‘Thin Line’ are two of my favourites. Throughout the 2000’s I wondered if this is Toronto’s biggest rap group because hundreds of people claim to be part of Point Blank, repping Regent Park to the fullest … ‘Born and Raised in the Ghetto’ is a CLASSIC CANADIAN RAP VIDEO!!! (And they killed it on Ed the Sock too!!)”


2000 - Kardinal Offishall - “Ol’ Time Killin’”

“Canadian Hip Hop Heavy Weight Kardinal Offishall has collaborated with Timbaland, Neptunes, Clipse, Akon, Jully Black, Saukrates, T Pain, Sean Paul, K'naan, Rihanna, Lil Wayne, Drake... AND he just became an A&R at Def Jam a month ago!! Northern Touch, The Anthem, Bikardi Slang, these are all classics but THIS track right here is my Ol'Time Favourite!"


Follow Chuggo for more of his Black History Month music countdown!

Facebook: Chuggo Freeman
Instagram: ChuggosCorner

For more Urban Music history, or reviews of quality Men’s work boots, check out Chuggo on Youtube.

Timberland Pro Work Boot Review by Chuggo (January 5, 2022)

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