Montserrat’s Samuel ‘Styler’ Ryan, Antigua’s first calypso king, dies at 84

Above is an album cover of one of the many recordings by Samuel "Styler" Ryan. He also sang with Milo and the Kings.

Samuel “Styler” Ryan, a native of Montserrat who became the first calypso monarch of Antigua, died Friday, March 31, 2023 at his home in St. Thomas, U.S. Virgin Islands. He was 84.

In 1957, Ryan won the inaugural Antigua Carnival calypso competition, defeating local favorite King Obstinate with a touching song called Water Wet Me Bed. He lost his crown to Obstinate the following year, and both men ended up migrating to St. Thomas in 1959.

During an interview in 2021, Ryan spoke at length about how he left Montserrat and began his calypso career.

Samuel Ryan was born May 19, 1938. Ryan said he lost his mother at a young age and never knew his father. He was raised initially by his grandfather, then sent to live with a family in the Jubilee Town section of Town Hill. The family owned a bakery, and Ryan says his adoptive mother worked him incessantly.

“I used to run away and go back to my grandfather’s house,” Ryan said. “And he would take me right back to the lady.”

In 1955, Ryan decided that he’d had enough. At that time, Montserrat had not yet built a proper commercial airport, and travel was still solely by sea. Boats such as Caribbee and Moneka sailed regularly between the islands. Ryan said he used to hang out at the docks in Plymouth. He befriended the captain of one of the boats and told him about his turbulent home life.

The captain agreed to transport Ryan to Antigua, and the 17-year-old left without his adoptive family’s knowledge. It is unclear how his documentation was sorted out, but when he arrived in Antigua, he stayed with a cousin in Green Bay Village. It was there that he met a young calypsonian named Paul Richards, better known as Obstinate.


By 1957, Antigua was ready to host its first official Carnival. Obstinate and others convinced Ryan to enter the calypso competition. “I had never sung calypso in my life,” said Ryan, who said a promoter gave him an initial calypso nickname, but it never stuck.

“I used to dance a lot,” Ryan explained. “A guy in Montserrat named Sonny Ben [real name Victor Davis] used to dance and roll his belly. I learned how to do it. They saw me doing it in Antigua and a guy said to me, ‘Boy, you can really dance with style.’ That’s how I got the name Styler.”

The first calypso show was held at the Deluxe Theater in St. John’s. The calypsonians were required to sing one original song and then cover a calypso of their choice, often a song from Trinidad. Styler performed Water Wet Me Bed, a song he wrote about his harsh upbringing. The chorus stated in part:

Come here little Harry,

Come help me bake me bread,

If I say Mommy ah still sleepy,

She throw water in me bed.

The lyrics were simple, but the authenticity of the tune likely swayed the judges.

“The night of the competition he was good,” Obstinate said of Styler during a 2021 interview. “The boy put some blows in us.”

Styler performs in Antigua in 2004. Water Wet Me Bed starts at about the 5-minute mark.

Styler was asked if he embellished any of the facts of the song. He seemed taken aback. “I don’t write anything if it’s not true,” he said with a serious tone.

In 1958, Styler entered again, but Obstinate prevailed this time. Said Styler, laughing: “I think the Antiguans decided they weren’t going to let any [outsider] win the crown again.”

That is ironic because many years later another Montserratian – Keithroy “De Bear” Morson – captured six crowns in Antigua. Ryan and Morson are the only non-Antiguans to win the crown.


After relocating to St. Thomas, Styler recorded several solo albums and also sang with Milo and the Kings, a popular V.I.-based band. Styler’s daughter Gwendolyn says her father relocated to New York with Milo and the Kings and later got married there and earned his U.S. citizenship. He returned to St. Thomas and eventually became a Born Again Christian and sang gospel. He worshipped at the Shiloh Seventh Day Adventist Church in Tutu.

Samuel Ryan also recorded gospel albums.

Other than his musical career, Styler held a variety of other jobs. He worked in a shoe factory while in New York and performed other odd jobs. In St. Thomas he worked at the famous Frenchman’s Reef Hotel. In later years he worked for the V.I. Government as a messenger and chauffeur, his daughter says.

A member of Ryan’s church says she saw him about a week before his passing and exchanged pleasantries. She says Ryan told her that his doctor said his heart is “not working right”. Ryan then said he had compiled a list of the hymns he would like to be sung at his funeral. It was a comment she found odd at the time, but is now deeply ironic.

Ryan is survived by five children: daughters Maria, Gwendolyn, Lorraine and Darissa, and son Daryl. He had 14 grandchildren.

Ryan’s homegoing will be held 10 a.m. Thursday, April 20, 2023 at Shiloh Adventist Church. There will be two viewings: 9 to 10 a.m. at Shiloh before the service, and 4 to 6 p.m. the previous day (Wednesday, April 19) at Turnbull’s Funeral Home in Charlotte Amalie.

Samuel “Styler” Ryan, circa 2020.



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