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Toronto's Greatest Hip Hop Music Videos Ever

  • Matthew Clarke
  • Apr 30, 2016
  • 10 min read

Top 20 Toronto Greatest Rap Videos in History

Article Written By Matthew Clarke

Watch snippets of all the Toronto hip hop music videos listed below on our official wwetv instagram.

Now I know this topic is going to be touchy with the Screwface Capital, but I promise to be objective as possible. This list imo represents the history of the city for those who don't know it. The rappers who made noise and an impact which helped shape our culture. At first glance this seemed like an easy task, but it really proved to be daunting as there are many great videos.

Many may not realize it or care to, but we got ourselves quite a catalog of music videos that can be rinsed pon the regular throughout our history. Take note that in creating this list I believed there had to be some balance as some of our greatest artists have not been able to have the financial backing on a regular for their music through various sources such as videofact or a major label which gives an imbalance of artists having an abundant number over others.

I tried to keep this in mind as some videos some may feel are missing which have superior production and quality, but this is about trying to give an overall painting with our various artists which I believe is fair to represent Toronto. My criteria was having the actual city represented in the music video and the impact it had with the streets and the mainstream.

I will also not be swayed by street politics and the truth of the matter is these videos and songs truly did and do reflect the different aspects of the city.

Honorable Mention

One of the biggest songs in Toronto history, but I just could not put in a list with videos containing Toronto. The video does not do this song justice and I do know about the politics here.

I just have problems with songs that announce themselves as an anthem before being called an anthem from the people, but I can dig what Kardi was trying to do here.

I know another Kardi Toronto anthem that did not make the list. Keep reading as I believe I have justified leaving these two videos out of the top 25.

The Jane and Finch rapper Robbie Khan shows his love for the city in this anthem that has Caribana as a backdrop.

This was one of the earliest music videos that dealt with the issues that were faced in Toronto which the city's mainstream were ignoring. Easy To Slip is a classic song and music video from Solitaire.

Mayhem Morearty - Out Here

The rapper who hailed from The Jungle area of Toronto made a lot of noise and created a rap movement from this very song and video. Unfortunately the video is no longer online.

IMG are known for being money getters in the streets of Toronto, but took Toronto trap music to Jamaica staying true to the roots of Toronto hip hop.

Regent Park's rap group TNT Sick Thugs made a classic tribute song and video with Missing You.

Toronto street group Concrete Mobb join up with the legendary Outlawz to make this gem of an undergound music video.

Bishop gained hip hop fame for his battling Jin and appearing on BET'S 106 & Park, but he delivered a heart felt song and video about living in Toronto with "Hard Times".

This under rated Rap duo from Rexdale dropped some gems of Toronto street life in the era where is was hardly popular in Toronto. The video aired on MuchMusic Television.

Gangis Khan made headlines when he signed with Raekwon's imprint ICE H20 Records when the Wu Tang Clan legend set up shop in Toronto. This music video explains beautifully what the dream of this Toronto rapper was growing up. It even has a flashback of young Khan looking at Maestro Fresh Wes' "Backbone Slide" video.

A very strong song and video which could only be told the way it was due to the rapper who executed it. Andreena Mills also proved to be a great addition to the song with her soulful singing. Frankie Payne also has an equally matching Toronto centric song with Saukrates entitled This Is My Life.

The beauty of this video is that apartment 310 can mean anywhere in the world, but we'll fit Lanez somehow into this list with this video.

One of the most heartfelt tribute songs by Toronto artists toward a fallen friend.

Before hooking up with Tyga and going on tour, Honey Cocaine was running in The 6. Many people forget this and she made them remember with this music video.

J Soul recently signed with Birdman to Cash Money Records. This music video is the most recent and in time may find its way onto people's top 25 list, but imo it is still too early. With that said it would be a crime to leave this awesome video and song from getting a mention.

The song and video that caught the eyes of Toronto of a then 15 year old Rexdale rapper known as Reema Major.

Before he was known for being Mr. TT, Robin Banks repped for the street of Toronto with Yonge Grove on Boyz In Da Woodz. The Driftwood / Shoreham Uptop Movementz did justice to the play off words on the American cult classic movie "Boyz In Da Woodz".

This video is a tight song that has tremendous visuals that divulge the streets of Toronto through great scenery using the backdrop of a classic hip hop movie Belly. You have the city’s biggest known star in the music video with a celebrity appearance from Louie Rankin who some know better as Ox and Teddy Bruckshot from vintage hood classic movies.

This video is one of the original representations of the street life of Toronto in the Rexdale area. This song ended up getting heard across the border ironically as Ghetto Concept became one of the first set of rappers who tried to get over the next side of the Niagara Falls.

Artists such as 50 Cent have songs such as "P.I.M.P.", but he wasn't actually being literal. The same can't be said for HDV. The artist according to CBC news, is a Grammy Award winner which is almost unheard of for a Canadian artist especially in urban music. “Proud Ta Be Pimpin’” song from his sophomore Higher Deeper Values release laid out the pimp game blueprint.

You won't find any better two artists out of the city and they both produced a classic imo. Just watch it and enjoy the music. Simple as that for the description of this. We don't actually know if this is in the many field streets on the outskirts of the Greater Toronto Area, but let's say it for the sake of the requirements of the list.

This was a toss up between the two. We’re That City imo is the better song and video, but Dirty Dot is no slouch as we see visuals of downtown Toronto. Either way this city is well represented in this.

The title of the track pretty much sums it up. We all know those late night or should I say early morning jams here in Toronto. Drake spoke on this to let the world know.

Once Infinite released this the streets of Toronto was on fire. Classic stuff which I have seen posted by even Americans on their youtube channels. Another toss up on the list as I can’t really choose which one is better in terms of the 360 Degrees video. Jully Black brought it on the vocals and the sample is classic.

A heartfelt letter to the music we all love. Daneo spoke for a lot of us on this track from the communities of Toronto about how some people were doing the art of hip hop.

This video dropped at perhaps the highest popularity of this Toronto rap pioneer as there was a lot of pressure on him from his label to deliver and from the streets of the Screwface Capital. There is even a folklore about an incident that won't be explained here which happened when Choclair was trying to film the video in certain parts of the city. At any rate this was one of the biggest videos to come out of the city.

Well if Solitaire's music video was being ignored these guys made sure to be seen and heard with this very gutter music video which made a lot of noise both in the streets and media. The original music video has not been seen since it debuted as a different version replaced it on MuchMusic after it was banned. You know your music and video are making an impact when CBC National News comes calling to make a documentary out of it.

15: The Dream Warriors Ludi - Another Jane and Finch rap group that ended up transcending the hip hop scene in Canada by crossing over to United Kingdom. The music video was set in Jamaica, but it clearly is a tribute for youth in Toronto with Caribbean roots.

This music video is what made everyone take notice of this Toronto legend. In the hey day of Mobb Deep and paranoia running wild in the era, Saukrates hit a home run with this.

Maestro Fresh Wes - Michie Mee - Jelleestone

This video I believe is the first ever Canadian hip hop music video to air on BET. When you got Toronto artists standing their ground with one of America's top lyricists it is both a joy to watch and listen to.

This video was released during a time when violence was at its highest in about a decade. It was like a build up of sadness and frustration all into one in this classic by one of the original street rappers.

P Reign represented not only for his block, but for the city that was mourning the most tragic incident in its history. Just a reminder that the music our artists in the city make can truly help in dire times.

Here are we are in the TOP 10 Music Videos that represent our city to the fullest!

Maestro went all out in this gem showing his national pride, but also sticking by our fallen hero at the time Ben Johnson. Something of a chance imo, but as illustrated by him admitting to turning down negative images of blacks completely in tune with his character. I give you NOTHIN AT ALL!!

KOS gets quite reflective in this joint and being the artistic soul he is delivers one of his best songs ever. Again, the way KOS creates his music videos you wouldn't know if he was from Toronto as the spots chosen could be seen as anywhere in the world. It doesn't take away that he is indeed a Toronto legend.

Sling Dadz featuring The Jane Strip

Blacus Ninjah, Leeno, Smugglaz, Frankie Payne, Page, Capital V, Clymaxx, Cause, Knemesis

There was once a time when this kind of collaboration was unheard of due to the gun violence that plagued the city especially on The Jane Strip. The original was great, but this was even greater. Sling Dadz somehow got the street rappers to unite for a classic song that represented the Strip to the fullest with even the bigger name artists.

Ghetto Concept returned to the scene with a bang with this single getting Maestro Fresh Wes, Kardinal, and even Snow to drop verses. One of the biggest tracks in Toronto history. There use to be a show called Too Much 4 Much where they would play videos and a panel would decide if the music video was too much too handle for viewers. This is where the name of this song originated from. I believe one of the first videos that received that handle was Apache’s “Gangsta Bitch”.

This video was a timely one for the original housing projects of North America. The area was being torn down, but Point Blank let the city know how it felt about Regent Park. Indeed one of the biggest videos and tracks to come down the pipe.

There is one hood track that topples #6 imo and it is this one. During the height of the "Summer of The Gun" this was EXPLOSIVE to say the least. Seeing all the street rappers uniting was a sight to see. Featuring Jugganaut, Stumps, V. D'ablo, Mayhem Morearty, Imperial, JB and Payback

The Original Hood Is Here

Of course it is going to be argued that Wavin Flag should be here alone instead, but this is about Toronto. You got Rexdale native with Queensbridge's Nas. You don't get any bigger than that folks. Wavin Flag is not just one of Toronto’s biggest songs ever, but just one of the biggest songs of the decade which was the theme song for The World Cup of Soccer. It's a video and song that represents the melting pot known as Toronto. He no doubt paved the way for Somalian rappers in the city such as Robin Banks, Top 5, and Layla Hendrixx.

This IS Toronto. The whole West Indian culture vibe hits it on the nail for me.

The only video which I can rank higher due to West Indian culture on this list is Michie Mee's classic. When you have Americans wanting to know who you are based off this you have done something right without alienating your roots.

#1. MAESTRO FRESH WES - Backbone Slide

The Greatest of All-Time!! Nothing was bigger than this! Toronto was on the come up at the time this dropped, but what happened to the scene a few years later is another story.

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