Calypso legend Rupert ‘King Swallow’ Philo passes away at 78

Photo credit: ABS TV
Rupert "Mighty Swallow" Philo performs in a legends concert during Antigua Carnival's 60th anniversary in 2017.

On Sunday, July 26, 2020, a small group of people visited Sir Rupert Philo – better known as King Swallow – at his home. The calypso icon had just been released from Mount St. John’s Medical Center. The visitors included Antigua & Barbuda Prime Minister Gaston Browne and calypso legend McLean “Short Shirt” Emmanuel.

In a video posted on social media, the men all sang Man To Man, Swallow’s 1978 song urging mankind to unite and not tear each other down. Swallow sang along while playing a toy drum set. Although he appeared frail, he seemed in good spirits.

“He said to me that he doesn’t have millions in the bank,” Browne said. “I reminded him of his contribution to the creative arts and nation building, which are etched in the hearts and minds of our people.”

On Friday, September 11, 2020, those same people were sent into mourning when King Swallow passed away following a prolonged illness believed to be kidney related. He was 78 years old. Swallow had been in and out of the hospital in recent months. In 2017 he was hospitalized in New York for an extended period.

His death marks the end of an era. Swallow, along with Short Shirt and Paul “King Obstinate” Richards, dominated the calypso scene in Antigua and much of the region for a half-century. The Short Shirt-Swallow rivalry even spilled over to Montserrat, where the two legends had their own faction of fans.

During the height of the rivalry, fans in Montserrat would get into heated arguments about which calypsonian was better. Antigua’s carnival, held in the summer, does not coincide with Montserrat’s December Festival. So Antigua Carnival had Montserrat’s complete attention each year, and the days of Short Shirt vs. Swallow were intense.

The peak of the rivalry came in the late 1970s. In 1976, Short Shirt released his classic Ghetto Vibes album with the mega-hit Tourist Leggo and blew away the competition in the calypso show. Swallow rebounded to win the crown in 1977 and 1978. He also won in 1973 and 1985.

“Whenever I win it’s a joy, because it’s a battle well fought,” Swallow once told the Antigua Sun newspaper. “I used to like the rivalry. As I always say, Short Shirt is one of the persons responsible for my elevation in calypso.”

The rivalry got thrown for a loop in the early 1980s when King Obstinate, who first won the crown in 1958 and then lived abroad for years, returned to Antigua. Obstinate brushed aside Short Shirt and Swallow and captured the crown in 1981, 1982 and 1983, then retired “undefeated” as he likes to say.

Photo credit: Kirthley Maginley
From left: King Obstinate, King Swallow, King Short Shirt, circa 1990s.

The Short Shirt-Swallow rivalry even seemed to get a bit personal later on when Short Shirt released the song Beauty and the Beast, to which Swallow responded with Barabbas.

The 1980s was the decade in which Swallow left his mark, not on the calypso stage but with his party songs. Tunes such as Subway Jam, Party in Space, Satan Coming Down and Fire in de Backseat became classics. He worked with the best producers of the era: Ed Watson, Leston Paul and Frankie McIntosh.

“He and Arrow helped soca to break out,” said Justin “Hero” Cassell, Montserrat’s 10-time calypso monarch. Arrow, Hero’s brother, also enjoyed success in the ’80s, especially with the iconic Hot Hot Hot.

Swallow ran the popular Calypso Pepper Pot tent during carnival. For several years in the early 1980s, Hammah International out of Montserrat was the house band.

“He was calm and soft-spoken, very professional,” says Silas Carty, Hammah’s lead guitarist, of Swallow. “Swallow was very easy to work with. I can never forget us backing him up on Party in Space. The day after he won the Road March he was on the truck with us singing it.”

Swallow would headline the shows at his tent, entering the stage in the wee hours by uttering his trademark phrase, “Saaaay What!!” as the band cranked up.

Swallow appeared on stage with Montserrat’s Keithroy “De Bear” Morson at the Antigua Calypso Monarch finals in August of 2019. He strummed a guitar as De Bear sang Let The Master Show You.

Swallow, Short Shirt and Obstinate have all dealt with serious health issues in recent years. In 1998, Obstinate suffered a stroke and was relegated to performing while seated. Short Shirt also had medical challenges and even turned to gospel in the late ’90s under the name Brother Emmanuel. He eventually returned to secular music.

Swallow was a five-time Road March winner: Pow Pow (1972), Push Ya, Push Dey (1973), Shake and Break You Bam Bam (1975), Party in Space (1983) and Satan Coming Down (1984).

Swallow was born in the rural village of Willikies on February 14, 1942 – just 14 days before the birth of his rival-to-be King Short Shirt.

Swallow has been honored many times by his country, the pinnacle coming in 2011 when he was awarded with the Knight Commander of the Most Distinguished Order of the Nation.

King Swallow Performs in Calypso Spektakula Tent in Trinidad, 1992


  1. So true about that rivarly that spilled into Montserrat. It made me a life-long Short Shirt fan. But who doesn’t like ‘Party in Space.’ Rest in Peace, Swallow.
    Thanks for this, Edwin!


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