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Wole Sentimenta was born Mayowa Oluwole to the family of Chief Samuel Ayilara Mayowa in Osun State, Nigeria. He hails from Ife central local government area Ile-Ife. He attended St Dominic High Shcool Akure, Ondo State. He studied Mass Communication in The Polytechnic Ibadan, Oyo State.
He started music as a child from RCCG choir Kings Parish, Akure, officially at the age of 11, when he was in secondary school he joined a gospel band in Akure called The Soul Fishers, where he led the band in an Afro song he wrote and won award of the Best Youngest African Gospel artist in 1997 while is band came 3rd among the 51 groups that competed at Fetshiter music Festival Held in Lagos in 1997.
He wasn't really encouraged to do music at a point when he was in the high school, so he had to stop on till he graduated from the institution. Wole moved to Lagos in 2004 and formed his own band Called Da Uptimist. the band major on Afro, Jazz and High Live music, which was inaugurated on the 27th July, 2008.
The name "Sentimenta came up while he was performing an Afro beat Song in the church at crossover night on 31 of December 2006, he wanted the audience attention on the lyrics of the song, he brought the music down and said "follow this musical progression sentimentally". There after, the song became an house hold song in the church and all over the place, so everyone that come across him since then calls him sentimenta.
He also released a promotion album in 2010 which has spawned a hit, "Like David",produced by Wole Oni and "Maromipin" produce by Sammyjayzee, though one of his least successful hits ever, did well in some charts. The promo CD is said to have faced distribution and sales problems, going unnoticed in some areas of the country
He delve into secular music in 2011 due irrational attitude of the christian leaders towards gospel musicians in Nigeria, after his performance in Delta State along side with Timaya at Ugwuashi Carnival on 25th Dec, 2011. He took up a courage of standing his own show AFRIKANNA NITE which was lunched on 1st May,2012 at Austina Continental Suites, Lagos. and the next edition was held at African Shrine on 25th Dec, 2013. He traveles on tour with charity organizations across African countries and he featured in a track SWEET HOME with BLACK BAZAR band in France in 2013, he latter got a deal with a management company "Sociallycued-pro International" in Texas, USA who secured him a record deal with Tate Music Group in Oklahoma. The record label released his first Debut Album of 10 tracks on 3rd June,2014.
Owuro yii, Celebrate are the hit tracks that are really making waves across the country on the local and international medias, internet links, social media networks and Telecommunication ring back tunes (AIRTEL, MTN, and ETISALAT).