Son of the Shadow: Sharlan Bailey builds on father's legacy

My father’s lessons: Sharlan Bailey is creating his own path as a singer, songwriter and producer, having learnt from his father, calypso icon, Winston “Shadow” Bailey. Photo by Sureash Cholai
My father’s lessons: Sharlan Bailey is creating his own path as a singer, songwriter and producer, having learnt from his father, calypso icon, Winston “Shadow” Bailey. Photo by Sureash Cholai

It is difficult growing up in the shadow of a famous parent. And for Sharlan Bailey it was especially difficult growing up in the shadow of iconic veteran award winning calysponian Winston “Shadow” Bailey.

Bailey spoke about his life, career and his new release for January 2018 High Times.

He told Sunday Newsday he wrote the song in 2016 for the 2017 Carnival but he found that people were missing the point of the song and thought it was only about legalising marijuana. He explained, however, the song is about a mixture of experiences.

“We living in these high times, and crossing these high lines, with these high minds we getting kicks, is high time something get fix,” Bailey sang.

In the song he sang about getting arrested after being held with marijuana in his short pants in his yard, about the assault on Bishop Clyde Harvey, high crime and the economy. He said the song did touch on the legislation of marijuana and pointed out many countries in the world were realising the benefits of this move.

“Why Trinidad taking so long?” he asked rhetorically.

Bailey is performing at Kaiso House and has been with the calypso tent since 2003, starting when his father was still there. He said people have a high expectation when your father is a public figure. When he was younger, Bailey wanted to avoid that pressure and would lie about who his father was and pretend his elder brother Shawn was a friend with the same last name.

“As a musician, a music producer and a songwriter I still live within that shadow. When you have an iconic parent like that and you running in the same field they have an expectation that you have to meet that. But the measurement of Sharlan Bailey to Winston Bailey is like telling a man with a size seven foot to put on a size 11 shoe. You have to allow to grow and be on my own speed.”

He said as an artiste he has never been in the Calypso Monarch finals and semi-finals but he has written for people who have gotten there including: Eunice Peters with None of the Above, co-written with Omari Ashby from Kindred: Lady Adana with Ready for the Truth; and Stacey Sobers. Last year Tamico “Spicy” Moore performed his song Missing You.

As a producer he has been able to work with the artistes he knew growing up as the son of Shadow and who he referred to as uncle and aunty. These include Mavis John, Duke, Bill Trotman, Brigo and Delamo.

He worked a lot with his father in the 2000s on songs like What You Come Here For and Naked Rhythm. Bailey said he was spoiled working with his father as a producer because Shadow, who has been doing music from 1970, knows exactly what he wants and the producer becomes just a musical translator. Bailey has also worked with his brother Shawn on the song Take One. He said his brother has started back recording in the past five years and has been testing the waters but for 2018 decided to take a rest.

Shadow strums: Calypso icon Winston “Shadow” Bailey strums a tune at his home in thie December 4, 2015 file photo.

Bailey has been playing instruments, including steelpan and keyboard, since age 7. He was inspired by late US musician Prince and his film Purple Rain where he played all the instruments and had the strength to challenge record companies. Bailey said Prince influenced him so much that he still goes into the studio, locks the door and does everything himself including vocals, background vocals, bars and guitar.

He began his career in the local music industry as a writer in the 1990s. He formed a rapso group called Platoon with Titus Lewis, son of the late calypsonian Mystic Prowler (Roy Lewis). They would perform at a bar in City Gate owned by Mystic Prowler together with Ozy Merrique.

He also auditioned for the now defunct Kiskadee Karavan but was rejected for sounding “too Trinidadian.” He was so depressed he went home and unstrung his guitar, but at three the next morning he restrung the guitar and started composing a song.

He cited Omari Ashby of rapso group Kindred as his biggest influence and described him as both a big brother and father figure.

“He made me recognise my talent.”

Bailey recalled Ashby was the first person to record Platoon and during the session told them there were not ready yet in terms of talent. Bailey left the studio angry but he began to change his attitude towards music, and it was Ashby who would bring him back into the industry. He said Ashby was still the person he would bounce ideas off of and would still give him an honest opinion.

Music, however, was not Bailey’s desired field and for many years he dreamed of becoming a member of the coast guard partly because he wanted to be in military life and partly because he loves the sea.

He explained he had uncles who were coast guard commanders and recalled his grandmother would show him coast guard books as a boy. In 1998, he successfully passed the exam and felt good about the subsequent interview but was rejected.

“I was so disappointed I didn’t know what to do next.”

He recalled chatting with Shadow and late calypsonian Carlton “Lord Blakie” Joseph, one of his father’s closest friends. Bailey performed some music and Shadow described it as a hybrid version of calypso and asked Blakie what he thought about it. Blakie responded that since Bailey made it he should be the one to name it. He still hasn’t chosen a name for his style.

Bailey has written and produced for many people but wanted to spend more time as an artiste and plans to release an album, Planet Dread, in June.

Asked if he would ever sing a song together with his father Bailey said the thought had crossed his mind but neither party ever pushed it. He recalled they did sing together live at Mas Camp when his father called him on stage.

Bailey said he knows all the lyrics to his father’s songs, when they came out and on which album. His knowledge is so vast at times his father would ask him about one of his own songs. He lamented his father was so influential to local music, including up to this day, but he was not respected.

“He is one of the only calypsonians to have hits for four decades and could win Road March in his pension age.”

He said his father had moved from analog to digital and from live recording to computer recording and had been successful in both worlds.

“Most calypsonians would disappear. He just keeps going.”

He said Shadow has always encouraged him but has also given him space to be himself. He added that Shadow has told him he liked the direction in which he was going and appreciated his musical abilities.

“I give thanks and praise for my father.”

Bailey said he achieved a number of the goals he set out for himself including working with certain artists and earning respect as musician. He added that he wanted to carry the music as far as it could go and as far as the Almighty would allow.

For more information on Bailey you can check out the DreadWizard Fanpage on Facebook; Dread Wizard is the title of a 1979 song by Shadow.


"Son of the Shadow: Sharlan Bailey builds on father’s legacy"

More in this section