16 poets entered the ring at Toronto’s Great Hall for the third annual Last Poet Standing Championship, presented by highly recognized poet and author Dwayne Morgan. The venue, packed to capacity, featured a real boxing ring with turnbuckles, two ring girls to introduce the competitors before each match and a championship belt for the winner.

Wearing a referee’s uniform, DJ Manifest warmed up the crowd with a mix of classic hip-hop, including LL Cool J’s 1990s hit “Momma Said Knock You Out”. The timeless track’s music video setting was very similar to where the poets would fight for the $500 grand prize. In a sport like boxing, where it’s all about aggression and beating the opponent, each competitor decided to take aim at issues that affected or bothered them like homophobia, bullying and relationships.

In a March Madness-style bracket, the winner moved on to the next round, while the loser went home. There were five judges, including Urbanology Magazine Editor-in-Chief, Priya Ramanujam, CP24’s Nneka Elliott, former Canadian Idol judge, Farley Flex and celebrated music journalist Master T. After both poets did a spoken word piece, the judges would vote on who would be moving on to the next round.

“I was looking for charisma, delivery and the way they put the poem together,” says judge and former Much Music VJ Master T.

In the event that all five judges voted for one poet, DJ Manifest would play the famous Chris Tucker line from Friday, “You got knocked the f*ck out.”

It didn’t take long for this to happen, as the eventual runner up Dan Murray received a unanimous win, in the first round of the night. He eventually lost to winner Philosofly, who won the crowd over with his personality in a best two-out-of-three championship round.

“I always make sure I put some of my good shit in the beginning because you want the crowd to fall in love with you. When they do, they’re more receptive with what you have to say,” says Brampton, Ontario native Philosofly, who couldn’t put a date on when he first started writing.

“It was that style on the way he presented, it was his level of confidence and the engagement of the crowd. He really had the crowd with him.” – Master T on winner Philosofly

As the playing field got stronger with every elimination and the crowd kept cheering in approval, finger snapping all throughout the competition showed how much the audience and competitors approved of each other’s work in a sign of mutual respect. What started out as matches with clear-cut winners, turned into rounds where it was increasingly more difficult to predict who would win.

“I’m the kind of guy that doesn’t try to have any expectations, because if I win it’s like ‘oh I expected that’ and it doesn’t feel as sweet,” says Philosofly.

When speaking about Philosofly and what made him stand out from the rest, Master T praised his uniqueness in delivery and the topics he covered.

“It was that style on the way he presented, it was his level of confidence and the engagement of the crowd. He really had the crowd with him.”

When asked about what he was going to do with the winnings, Philosofly said he would be reinvesting them into his musical career.

Words By. Cameron Da Silva + Photos By. Janelle Scott-Johnson