Winston 002

Hewitt, Winston

Origin: Kingston, Jamaica - Toronto, Ontario, 🇨🇦

Born the 6th child from a fleet of 14, Winston lost his dad when he was just 18; with the burden of taking care of his family left on his shoulders. He remembers how hard it was filling his dad's shoes, but the help and love of his brothers and sisters and the love of his mother was the motivating factor, which ultimately led to his success. Hewitt in an interview will X-Tratainment could not stop singing his mother's (Mary Hewitt who now resides in May Pen) praise and the admiration of her strength in raising 14 children, most of whom she raised solely on her own, after the passing of his father.

In addition to being the driving force behind the Canadian Reggae Music Awards, Winston is the original lead singer and one of the founding members of one of Jamaica's top international reggae vocal group 'The Pioneers'. Hewitt, working out of Toronto, Canada has taken part in most of the reggae festivals across Canada and around the world. Winston has performed with superstars such as Jimmy Cliff, Bob Marley, Dennis Brown, Marcia Griffiths, Freddie McGregor, Jackie Edwards, Dobby Dobson, Ernie Smith, Millie Jackson, Jerry Butler, The Manhattans, Melba Moore and many others.

Hewitt is considered one of the top reggae artists in Canada. He has so far nine albums and 18 singles to his credit. In 1987, Winston hit the No. 1 spot on the reggae charts, in 5 cities across Canada and the USA with an original single entitled 'You're My Boopsy' which also hit the top 10 charts in England and Jamaica. He also hit the No. 1 spot again in Canada, in 1995, with a song entitled 'We Need More Love' a duet with Inspector Lenny, which stayed on the reggae charts for 11 weeks.

Winston as the leader of the Dynamics received an award at the CHIN INTERNATIONAL PINIC in July 1973 for his continuing support to multiculturalism in Canada. He also received an award in 1986 from the C.M.R.A.C. out of Toronto Canada, for his outstanding leadership and distinguished contribution to the reggae industry. In 1987, he received a certificate of appreciation for his continued support and contribution to community programming within the Graham Cable TV/FM viewing area, In Ontario Canada, The Jane/Finch Concerned Citizens Organization (J.F.C.C.O.) and the United Way presented Winston with an award for outstanding community service in 1988.

In 1990, at the Ninth Annual International Reggae Music Awards held in Atlanta, Georgia, he was presented with an award for his 'Outstanding Contribution to the Growth of Reggae Music'. On May 4th 1991, Winston Hewitt was presented with an award for 'Most Improved Reggae Entertainer' of the year at the Tenth Annual International Reggae Music Awards held in Montego Bay Jamaica W.I. In 1993, he also received an award from the Association for the Advancement of Reggae Music in Alberta (AARMA) in recognition of his contribution to the 'Advancement of Reggae Music in Canada'. When May II was officially declared Bob Marley Day in Toronto, Hewitt was presented with the Bob Marley Memorial Award at the ceremony for his 'continued contribution and dedication to Reggae music in Toronto'.

In 1999, the Jamaica Day Celebration Committee, presented an award of merit for outstanding achievement in the field of music to Winston Hewitt. Also in 1999, The Marcus Garvey Foundation - Toronto Chapter, presented the Marcus Garvey Award for outstanding contribution to the Canadian Reggae Music industry to Mr. Hewitt. In 2003, Winston received The Ronald Alphonso Memorial Award for 30 or more years' contribution to the reggae industry in the world. Also, in July of 2003, Winston received a lifetime Achievement Award from the Urban Music Association Canada (U.M.A.C.) for his extraordinary dedication and excellence in the promotion, celebration and enhancement of reggae and urban music in Canada. To name a few. So far Winston have received over 20 various awards local and international.

Despite the responsibilities of organizing a show of that magnitude, Winston still finds time for the studio and his singing career. For six months out of the year, Hewitt tours extensively. His latest releases is a collection of some of his greatest R&B, Soul, Easy Rock and Reggae hits entitled 'Winston Hewitt's Greatest Hits Vol. #I. and Winston Hewitt Reggae hits vol. #1. Which is available now in stores. In the meantime, Winston is still working on 2 new CD's containing some more of his greatest Reggae hits which will be available soon.

The Pioneers are a Jamaican reggae and soul vocal trio, whose main period of success was in the 1960s. The trio has had different line-ups, and still occasionally performs.

The Pioneers were formed in 1962 by brothers Sydney and Derrick Crooks, and their friend Winston Hewitt. Their early recordings "Good Nanny" and "I'll Never Come Running Back to You" were self-produced at the Treasure Isle studio in Kingston, Jamaica, using money lent to the Crooks brothers by their mother and appeared on Ken Lack's Caltone label.

Several other singles followed, none of them hits, before Hewitt emigrated to Canada in 1966. Hewitt was replaced for around a year by former Heptone Glen Adams.

Canadian Reggae Music Awards, March, 2004
Winston Hewitt took me back 20 years ago when he first came up with the idea of a Canadian Reggae Music Awards. He tells me "Back in 1984 I had been a reggae artist for years, I was working construction with my brothers. One night, I was sitting down watching The American Music Awards. The Eagles had a song out called "Hotel California" which in my mind was reggae, Culture Club's big hit was "Do You Want To Hurt Me", Tina Turner's "What's Love Got To Do With It" and lots of other songs won Awards during this period in 1984. No reggae artist had been nominated anywhere, like Bob Marley, Gregory Isaacs and Dennis Brown to name a few. I then realized that for reggae artists to have Awards to put up on their wall, they were not selling enough records to have a Gold or Platinum. That is when the idea came - to start up a Reggae Awards". Now, 20 years later Winston' s dream is celebrating it's 20th Anniversary. Over the years, like any veteran in the music business, Winston has seen many changes. He says, "Every time a reggae song hits the mainstream it becomes a Number 1, for example, UB40's "Red, Red Wine", Ken Boothe's "Everything I Own". Same as today, although they have changed the beat of the reggae beat, artists like Sean Paul and Elephant Man have reached the mainstream. Unfortunately, most of our Canadian artists do not have the funds, therefore they go independent". He continues to say, "A lot of the people who produce here do not have the funds to use professional studios but use demo studios to do their recording and therefore cannot compete. These artists that are struggling do not use proper engineers. When you go into a real studio they spend hours and hours on one line on the controls to balance the music properly to get the proper sounds, most studios do not have compressors to make the music tight. The artist, engineer and producer have to know what sound they are looking for". Winston continues to say, "That you get what you pay for. Also the environment that you live in has a lot to do with what you eat or drink, has a lot to do what you are listening to and how you carry yourself. The environment that we live in is not a reggae or R&B environment, we don't hear this music 24/7 on a radio station and we do not have the sound drilled into us. Unfortunately that is why so many of our Canadian artists leave Canada to make it!

If you are an R&B artist you have to go to where it is played. You go there and learn and mix in that environment ". Winston tells me that over the past 20 years he has seen so much Canadian talent grow and states that we are blessed with our Canadian artists. " The Reggae Awards are really to expose Canadian talent and for them to promote themselves and hopefully make it to the mainstream level". He says "every year is a learning tool and every year they make changes, hopefully for the better". This year, the Awards take place on Sunday, March 21st at 7 p.m. at the Travel Lodge Hotel, 2737 Keele Street, Toronto. As this is 20th Anniversary, they are planning to hold a pre - Award Party with some of the artists on the Saturday night. A dynamite show has been planned; one of the best performance wise and everyone is very excited. Ken Boothe is one of the featured artists, with Johnny Clarke, Dobby Dobson and Half Pint, an artist who came along in the 80's who has held his own. His song "Greetings I Bring From Jah" is classed as an Anthem. Also Barbara Jones along with a host of Canadian Artists.


Featured Albums




Compilation Tracks


Screenshot 20230901 084025 whatsapp

WhatsApp Inducted into MOCM

Winston 003


Winston 001



Hewitt, Winston


Hewitt, Winston

Winston 002

Hewitt, Winston


No Video