| Year | Artist | Video | | 1990 | Maestro Fresh-Wes | "Let Your Backbone Slide" |
| 1991 | Dream Warriors | "My Definition of a Boombastic Jazz Style" |
| 1992 | Organized Rhyme | "Check the O.R." |
| 1993 | The Maximum Definitive | "Jungleman" |
| 1994 | Devon | "X Marks The Spot" |
| 1995 | k-os | "Musical Essence" |
| 1996 | Saukrates | "Hate Runs Deep" |
| 1997 | Rascalz | "Dreaded Fist" |
| 1998 | Rascalz f. Choclair, Kardinal Offishall, Checkmate & Thrust | "Northern Touch" |
| 1999 | Infinite | "Take a Look" |
| 2000 | Choclair | "Let's Ride" |
| 2001 | Baby Blue Soundcrew f. Kardinal Offishall, Sean Paul & Jully Black | "Money Jane" |
| 2002 | Swollen Members f. Moka Only | "Fuel Injected" |
| 2003 | Swollen Members f. Nelly Furtado | "Breathe" |
| 2004 | Jelleestone f. Elephant Man | "Who Dat" |
| 2005 | k-os | "Man I Used to Be" |
| 2006 | Classified | "No Mistakes" |
| 2007 | Belly f. Ginuwine | "Pressure" |
| 2008 | Belly f. Mario Winans | "Ridin'" |
| 2009 | Classified | "Anybody Listening" |
| 2010 | Drake f. Trey Songz and Lil' Wayne | "Successful" |
| 2011 | Classified | "That Ain't Classy" |
| 2012 | Drake feat. Lil Wayne and Tyga | "The Motto" |
| 2013 | Drake | "Started From the Bottom" |
| 2014 | Drake | "Worst Behavior" |
| 2015 | P Reign f. Drake & Future | "DnF" |
| 2016 | Drake | "Hotline Bling" |
| 2017 | Tasha the Amazon | "Picasso Leaning" |
{{MuchMusic Video Awards}}