Here are the winners from Pretty Boy D-O’s freestyle challenge

Out of over 700 submissions from all over Africa, Boy Oleko emerges as #1

These days, artists no longer rely solely on their music to connect with the fans. Thanks to social media, which grants one immediate access to all of your favourite artists, marketing music has experienced a welcome surge over the past decade in the most authentic ways.

Pretty Boy D-O has endeared his audience over the years with his authentic expression of self, and larger-than-life personality. With a strong presence on social media, using slang such as his most recent, ‘Lord protect my steppings’, his influence on popular culture is clear, and now he’s invited his able fans to join him in a freestyle challenge.


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Drum roll please…

Following the release of his latest single “Living in Bondage”, the Lagos-based rapper placed an open call for freestyle submissions to the song in partnership with OffTopApp.

The challenge officially kicked off last month, and has now drawn to a close after receiving over 700 submissions from around the continent. In partnership with the man himself, The NATIVE team sorted through all these submissions and picked the top 10 entries in the challenge. We are pleased to announce the winner today, rapper, Boy Oleko who’s Instagram will show that he’s he’s gaining traction and building his own fan base organically, with covers of some recent hits; Ruger’s “Bounce” and Omah Lay’s “Understand”.

For this competition, his cutting raps and painfully honest lyrics, especially his reference to #JusticeForTina, and passing commentary on the dire state of our country earned him the top spot in the #LivingInBondage.


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Close runners up in second and third place are CJ Zuma and J Will who are closely followed by White Flavour OD in fourth place. Our other worthy entries rounding off the finalists in the top 10 were; Milly Wine, Ameen, Preshtunez, Christina Qween and Jcee Gram, whose impressive raps gave DO the NATIVE team a tough decision to make. Ultimately, there can only be one winner, congratulations to Boy Oleko.

Check out all the freestyle submissions from the Top 10 finalists below.

Featured image credits/NATIVE

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