Orlando Octave at the tender age of three (3), started singing and performing for family and friends in his hometown at Khandan Street in Rio Claro, Trinidad and Tobago. He attended St. Therese R.C. School in Rio Claro, when in the year 1999 at the age of ten (10), he got his first taste of the limelight by participating in a competition called “Promenade Summer”, which he was the winner of.
This gave Orlando the encouragement to pursue the title of Junior Soca Monarch at the age of eleven (11) in 2000. Though not successful in achieving the title, he was thrust into the spotlight and was chosen by Socarama to be part of a tour alongside other artistes, scheduled to perform at Madison Square Garden for the Fulton Boys & Girls College. During his stint in the U.S.A., Orlando entered the Labour Day Soca Competition and won. Upon his return to T&T, he was chosen by NYAC/NORS as one of the Top Twenty Stars of Tomorrow.
These series of events catapulted this young talent to participate in the Coca-Cola Sponsored Schools Tour across T&T for the duration of 2001 through to 2003. Once again in 2004, Orlando Octave, better known as the “D Original Rude Boy”, made an attempt at the Junior Soca Monarch and triumphantly copped the tile with his winning composition “Proud of Rude Boy”. After winning this title, Orlando was selected by the Inter-Cultural Performing Arts of T&T to be part of a one month long tour in the U.S.A. alongside other artistes.
At the end of this tour, he returned to T&T and graced several Carnival fetes with his positive lyrics and conscious vibes. Orlando was now successfully riding the entertainment wave. He was chosen by the Ministry of Education to participate in their Schools Tour Programme. Determined to keep moving forward, “D Original Rude Boy”, took to the stage again for the Junior Soca Monarch in 2005 and placed second with his composition “T&T”. In the year 2006, not forgetting the importance of a sound educational background, Orlando chose to bow out of the limelight and focus on his studies; this helped him to obtain six (6) O’level passes.
Fast forward to 2008, the “D Original Rude Boy” in addition to being nominated for a National Youth Award, he burst back out onto the music scene with his hit single, “Darkie”. At the moment he is making waves across the country with this new single, which was also brought to the public via his participation in a Guinness sponsored tour across T&T.