In 2009, when he was a fresh face in hip-hop without an album to his name, the now-legendary Drake went to HOT 97.0 to drop an amazing freestyle on the renowned Funk Flex show. Not only was it huge at the time but Drake’s performance is still talked about to this day. One of the biggest topics turned out to be the infamous footage of him spitting a written freestyle on his phone.
In an exclusive interview with DJ Juanyto, the HOT 97.0 genius who first caught wind of Drake, the radio host spoke about how he first met Drake and detailed the behind-the-scenes lead-up to the freestyle.
Opening up about ho whe first found out about drake Juanyto explained, “The first time I met Drake was in Toronto in ’08, with [DJ] Cipha Sounds. We would be there for Caribana, he would DJ, and I would go there and help him a lot. One night, we met Drake at a diner, and he gave us a CD at that time…I think it was Comeback Season, [the one] where he had the peat coat on the mixtape cover. We listened to this mixtape on our way back from Toronto, we drove, and we listened to this whole mixtape.”
He continued, “Fast-forward Drake builds a bigger buzz now the So Far Gone music starts coming out which is ‘The Best I Ever Had’ and Flex got an ear of it, and he was like ‘I need this kid to come by the station!”
Elaborating on how Cipha Sounds organised the date, Juanyto unveiled, “Cipha sets up the meeting, not knowing it was going to be a freestyle. So I grabbed the camera, and I started shooting because I was like, you got to document this moment.
That was pretty dope seeing that come about and seeing an artist using a Blackberry, using a mobile device to actually do the freestyle. I had never seen that in my life! We had seen the pen and paper but actually reading it off the phone during the freestyle, no.”
The iconic 2009 freestyle from Drake was his first appearance on mainstream US radio and his first live freestyle on a commercial hip-hop station in America. Ever since, the Canadian has been on an upward trajectory and is now one of the most successful rappers in the world.
You can watch his 2009 freestyle below.