While there have been some amazing hip-hop albums over the years, it’s a genre that’s truly thrived in the singles format. You just can’t get a complete look at the history of Toronto rap if you don’t take into account all those great releases. To make sure we weren’t forgetting any essential classics, we consulted Maestro Fresh Wes, DJ Fase, Never Forgive Action resident DJs Dalia and Numeric as well as NOW contributors Anupa Mistry and Kevin Ritchie.
1. Maestro Fresh Wes
Let your backbone slide (1989)
This smash single put Toronto hip-hop on the map and gave a generation of MCs hope that they could make an impact beyond our city. Drop this track at a party even in 2012 and the entire dance floor raps along to every word.
Best I Ever Had (2009)
Originally on his So Far Gone mixtape, Best I Ever Had introduced Drake to the world and forced T.O. to take the future superstar seriously. Other Drizzy hits may have charted higher since, but this was the turning point.
3. Michie Mee
Jamaican Funk (1990)
Like Maestro, Michie Mee is an indisputable Toronto hip-hop pioneer. The first Canadian MC to get an American record deal, she helped establish that Toronto’s hip-hop identity would recognize our unique cultural diversity.
Let’s Ride (1999)
The first single off his Juno Award-winning debut album, Ice Cold, Let’s Ride established Choclair as one of the leaders of the late-90s scene.
Father Time (1995)
While he never enjoyed the international success he deserved, Toronto heads know how important he was. This early single captures him at his best.
6. Ghetto Concept
EZ on The Motion (1995)
Originally a duo, this 1995 Juno-winning single introduced Ghetto Concept’s third member, Infinite, and features a Quincy Jones-sampling beat by Da Grassroots.
7. Main Source
Looking at the Front Door (1990)
Some sources describe Main Source as an American group because of the involvement of NYC producer Large Professor, but Toronto heads know the truth.
8. Kardinal Offishall
Ol’ Time Killin (2001)
BaKardi Slang may have sold more copies worldwide and helped establish the term “T-dot” internationally, but Ol’ Time Killin is the track that the locals love.
9. Dream Warriors
These jazz rap pioneers had bigger hits, but this ode to the African/Caribbean board game stands the test of time even better than Wash Your Face or My Definition.
10. Da Grassroots
Drama (feat. Elemental) (1995)
This production team defined the sound of local hip-hop in the 90s, and this moody early single featured their sound at its best.