Calypso Contest and the Jolly Boys


The Jolly Boys have experienced a rebirth in recent years, perhaps due in part to their calypso coverage of Amy Winehouse’s “Rehab,” which is a spirited and novel rendition. I especially love their calypso cover of Iggy Pop’s “Passenger.” It is said that their name was given was given to them by Errol Flynn since they frequently played for his shin-digs in Port Antonio. I don’t pretend to know much about the Jolly Boys, but I do want to share here two articles that I recently found in the Star Newspaper that are related to the Jolly Boys. One is an advertisement for a Calypso Band Contest sponsored by Wray & Nephew from the Star on June 19, 1962. The Jolly Boys entered this contest and performed quite well, as evidenced in the next article I found.


On July 17, 1962, the Star Newspaper wrote in an article titled, “Jolly Boys Top Calypso Contest,” their success was profiled. The article stated, “Port Antonio, Saturday. A large crowd turned out at Delmar Theatre Wednesday night last when the J. Wray & Nephew Calypso Band Elimination All Island Contest was staged. The Wray & Nephew band, led by Trenton Spence, entertained with many numbers then the artistes—Kid Harold who received a big hand from the audience, Herbert Russell and his partner thrilled all who watch them go through their acrobatic dancing and marveled at the precision of the team, Lascelles Perkins whose magnificent voice was heard to good advantage, and Annette Clarke—all entertained the audience prior to the more serious part of the programme. Two bands entered the contest which was judged for appearance, delivery, musical technique, and the lyric and rhythm for a Wray & Nephew Calypso for Independence. Mr. Jimmy Cashman, the firm’s representative, was master of ceremonies, and the judges for the contest were Messrs. Mortimer Geddes, Headmaster of Titchfield School, G. P. Eubanks, deputy supt. of Police, and Miss C. N. Grant. It was a keen contest between the two bands and resulted in the Jolly Boys taking the edge over Jamaica Reef Calypso Band. It was a proud team consisting of Noel Lynch, bandleader, Moses Deans, Martel Brown, Derrick Henry, Alexander Brown, who came on stage to receive the judges report. The Jolly Boys won £25 prize for the eliminations and they will compete at the finals to be held at the Ward Theater in Kingston on Thursday 19th of July. Cartons of rum were donated to each judge, to the Rev. Father Gardiner Gibson, SJ who congratulated the winners, and the leaders of both the contesting bands by Mr. Cashman on behalf of the company. The grand finals will be held in Kingston on Thursday next (July 19).”


Here’s another advertisement that ran in the Daily Gleaner on the day of the big event, July 19, 1962:


I can’t find any article or write-up on who won this contest, but I did find a few more articles and advertisements for the Jolly Boys, which I post here.




And here is an article on mento which features The Jolly Boys written by Roy Black.


To hear a little of the Jolly Boys, check these links out to three of my favorite songs.

Here are the original members, or a few of them, recorded in 1989 with No Rice, No Peas, No Coconut Oil:


The Passenger:

Blue Monday:

1 thought on “Calypso Contest and the Jolly Boys”

  1. Another great article Heather. You should have seen the crowd at Sierra Nevada. The Jolly Boys had everyone on their feet!!


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