It’s hard to remember a time when Drake wasn’t the biggest rapper in the world. He is Canada’s most successful AND influential artist of the 21st century. As both a rapper and a singer he has pretty much single-handedly put our country on the map for hip-hop and R&B. 

He is a five-time Grammy winner, has 85 million monthly listeners on Streaming Services- more than any other rapper - and holds the record for most number 2 singles on the Billboard Hot 100. He also ranks fifth behind the likes of the Beatles and Mariah Carey with the most number 1 singles.

By the mid-2000s when Drake embarked on a rap career, Canadians already knew him from Degrassi The Next Generation. Of course, His name wasn’t Drake back then, it was Aubrey Graham, a teenager from the Toronto neighbourhood of Forest Hill, who caught his break when he was cast as Jimmy Brooks. 

Aubrey left the show during its eighth season to pursue music full time. As much as he had become a star on Canadian television as an actor, he wanted to go global with his music career. 

Drake dropped his first mixtape, Room For Improvement, on Valentine’s Day 2006. He was still working on Degrassi at the time, but had already made some connections in the rap game. Drake would wait a year before he followed up Room For Improvement. But in that time he had already made connections that would help him advance his music. Among the producers he brought in to make beats for him were 9th Wonder, who had worked with Jay-Z, Destiny’s Child and De La Soul, Atlanta’s DJ Toomp and a couple of local guys: Boi-1da once, and Noah “40” Shebib.

Jas Prince was an aspiring rap mogul from Houston, Texas looking to become a legit rap mogul like his father, J Prince, founder of Rap-A-Lot Records. 

While he was looking around MySpace one day in 2006, he found Drake’s artist page and saw a lot of promise in the tracks posted. He played some of the songs for his dad, J Prince, but he couldn’t hear what Jas was so excited about.

Then one day Jas shared Drake’s music with New Orleans rapper Lil Wayne, who had just struck gold with his album Tha Carter II. At first, Wayne wasn’t impressed.

Jas persisted though, and months later on New Year’s Day, he played Wayne a few more songs in the car, one of which was Drake’s remix of Wayne’s own “A Milli,” a song that had yet to be released commercially. That was the moment Drake became legit.

Jas put Lil Wayne in touch with Drake and the next day Drake was flying to Houston to meet with one of his heroes.

Drake ended up joining Lil Wayne for his I AM Music Tour at the end of 2008 and the Toronto kid quickly became the New Orleans legend’s protege. 

Every opportunity they could get they would record new tracks, some of which ended up on Drake’s next project. So Far Gone, Drake’s third mixtape, was released on February 13, 2009. One song on the mixtape stood out more than others and it began to catch fire, leading Drake to make a video with one of the biggest artists in the world.

This is the true story of Drake's 'Best I Ever Had' with newly unearthed audio from MUCH, as well as sound from Rap Radar, MTV News, Myspace, and CBS News.

It’s hard to remember a time when Drake wasn’t the biggest rapper in the world. He is Canada’s most successful AND influential artist of the 21st century. As both a rapper and a singer he has pretty much single-handedly put our country on the map for hip-hop and R&amp;B. 
He is a five-time Grammy winner, has 85 million monthly listeners on Streaming Services- more than any other rapper - and holds the record for most number 2 singles on the Billboard Hot 100. He also ranks fifth behind the likes of the Beatles and Mariah Carey with the most number 1 singles.
By the mid-2000s when Drake embarked on a rap career, Canadians already knew him from Degrassi The Next Generation. Of course, His name wasn’t Drake back then, it was Aubrey Graham, a teenager from the Toronto neighbourhood of Forest Hill, who caught his break when he was cast as Jimmy Brooks. 
Aubrey left the show during its eighth season to pursue music full time. As much as he had become a star on Canadian television as an actor, he wanted to go global with his music career. 
Drake dropped his first mixtape, Room For Improvement, on Valentine’s Day 2006. He was still working on Degrassi at the time, but had already made some connections in the rap game. Drake would wait a year before he followed up Room For Improvement. But in that time he had already made connections that would help him advance his music. Among the producers he brought in to make beats for him were 9th Wonder, who had worked with Jay-Z, Destiny’s Child and De La Soul, Atlanta’s DJ Toomp and a couple of local guys: Boi-1da once, and Noah “40” Shebib.
Jas Prince was an aspiring rap mogul from Houston, Texas looking to become a legit rap mogul like his father, J Prince, founder of Rap-A-Lot Records. 
While he was looking around MySpace one day in 2006, he found Drake’s artist page and saw a lot of promise in the tracks posted. He played some of the songs for his dad, J Prince, but he couldn’t hear what Jas was so excited about.
Then one day Jas shared Drake’s music with New Orleans rapper Lil Wayne, who had just struck gold with his album Tha Carter II. At first, Wayne wasn’t impressed.
Jas persisted though, and months later on New Year’s Day, he played Wayne a few more songs in the car, one of which was Drake’s remix of Wayne’s own “A Milli,” a song that had yet to be released commercially. That was the moment Drake became legit.
Jas put Lil Wayne in touch with Drake and the next day Drake was flying to Houston to meet with one of his heroes.
Drake ended up joining Lil Wayne for his I AM Music Tour at the end of 2008 and the Toronto kid quickly became the New Orleans legend’s protege. 
Every opportunity they could get they would record new tracks, some of which ended up on Drake’s next project. So Far Gone, Drake’s third mixtape, was released on February 13, 2009. One song on the mixtape stood out more than others and it began to catch fire, leading Drake to make a video with one of the biggest artists in the world.
This is the true story of Drake's 'Best I Ever Had' with newly unearthed audio from MUCH, as well as sound from Rap Radar, MTV News, Myspace, and CBS News.

Do you remember where you were the first time you heard Outkast tell you to 'Shake it like a Polaroid Picture'?

How about when Nickelback told you to 'Look at this Photograph'?

Or when Taylor Swift provided the soundtrack to your Love story?

Join Ruby Carr as she takes you through the biggest songs in the world - with new interviews and newly unearthed archive footage from the artists themselves.

Subscribe on iHeartRadio or wherever you get your podcasts!

Do you remember where you were the first time you heard Outkast tell you to 'Shake it like a Polaroid Picture'?
How about when Nickelback told you to 'Look at this Photograph'?
Or when Taylor Swift provided the soundtrack to your Love story?
Join Ruby Carr as she takes you through the biggest songs in the world - with new interviews and newly unearthed archive footage from the artists themselves.
Subscribe on iHeartRadio or wherever you get your podcasts!

Join Myles Galloway as he takes you through the biggest songs in the world - with new interviews and newly unearthed archive footage from the artists themselves.