After winning Culturama 43’s Calypso competition Aug. 5, Andrew “Hollywood” Nisbett will now head to Antigua to represent Nevis and go after another title. Hollywood won his second calypso crown in 25 years of performing, dethroning last year’s king Dis and Dat on his way to the crown.

Hollywood will now perform at the 21st Annual Leeward Islands Calypso Competition at the Anguilla Summer Festival on Saturday, Aug. 12. This is the second time that Hollywood has gone to Anguilla, and his manager Roger Fyfield explained that Hollywood and his team are excited and ready for the opportunity.

“Last time we didn’t place in the top three, but this year is a different kettle of fish,” Fyfield said. “We have prepared, and King Hollywood has been performing since 1992, consecutively and consistently, so we are going out with 25 salutes.”

Hollywood and Fyfield have developed a unique strategy to face two unique competitions in such a short amount of time. After noticing that songs created solely for Culturama don’t resonate as well with audiences at the Leeward Islands competitions, they wrote music that they hope everyone can identify with. “My Best Guess” and “The Real Disaster” are the two tunes written and composed for the competition on Nevis, and Hollywood will carry those over to Anguilla on Saturday.

“These two pieces could be [sung] and easily adopted to any competition anywhere in the world,” Fyfield said. “We have trust and confidence in our material, and hopefully the judges will give us the nod again as they did here on Nevis. We are very optimistic of our chances of bringing back something. Knowing Hollywood, he’s very patriotic, so he’s going out not to just represent himself, but also put the entire Nevis on his shoulders.”

Hollywood and his team set out Thursday to ensure they get enough time to practice their performance before Saturday’s show. Fyfield was confident about their preparedness for this event, partly because of his years of experience and also because of the feedback Hollywood received at his previous live shows.

“Each time one competes, it’s a different vibe and feeling, and each time you go on stage your confidence builds for the next time,” Fyfield said. “The thing about competing is that you get the real live feeling and feedback from the crowd. Especially in open air, you get a better sense of the sound and how people receive it. “We got the opportunity last week, we recognize that the crowd and the judges receive it well, so through that we are 80 percent prepared.”

The last 20 percent comes with practice and getting comfortable with the All-Star Band Hollywood will be playing with on Saturday. The band is a professional one, so Fyfield is confident that as long as they can get at least two practices in before the show they will be ready to go. Their first practice was scheduled for Thursday after they arrived, showing that Hollywood is taking no time off in his chase for the crown.

“We’re asking one and all to support him,” Fyfield said. “Thank you to the fans and critics alike. When one puts themselves in the public spotlight as a public figure such as a Calypsonian, you must be able to take constructive criticism and praise that will help you know where you’re going wrong. With that, you can only develop and become better at what you do.”

Hollywood has spent 25 years developing his craft and it will be on full display Saturday.