The America’s Cup did not bring Nadanja Bailey fame or fortune but, a year later, the comedian beams as he recalls how much fun he had as emcee. Lifestyle spoke with him about his experience.

Nadanja Bailey’s biggest complaint about the America’s Cup is that it ended too soon.

The comedian spends his days driving people around and bartending; being able to devote a full 30 days to entertainment felt like heaven.

“I like driving a taxi and telling people about Bermuda, but that’s not my passion,” he said.

“I love entertaining — just gimme da mic! A whole year later and I am still asking, ‘What now?’”

He has had nothing that compares with the America’s Cup since. His biggest gig was the MS Amlin Bermuda World Triathlon in April.

“Hopefully, something will come up,” he said.

“There is most definitely a lack of opportunity on the island. This is a place of business, but we all still like to have fun and entertain. Why can’t we keep our local entertainers working 12 months out of the year?”

The beauty of the America’s Cup was that every day was “the best day”.

“It was fun for me,” he said. “I am upset it is not going on any more. Anyone who did not go to the America’s Cup Village in Dockyard missed out on a great venue. I felt like I was not in Bermuda.”

He interviewed for the job last April. Christian Peer, the entertainment co-ordinator for the America’s Cup, seemed impressed that he had introduced the likes of Beyoncé and Alicia Keys when they performed at the Bermuda Music Festival in 2008.

“I don’t know how many people I was up against,” Nadanja said. “I know there were other people in line.”

He was chosen, along with Glenn Jones the Bermuda Tourism Authority’s director of strategy and corporate communications.

“There are so many other great emcees in Bermuda, I always am thankful for the opportunity,” Nadanja said.

“The fact I was even shortlisted to be a local host was awesome. I would never take that for granted.”

He admitted he did not fully know what the America’s Cup was when he signed up. He learnt quickly. His job was to introduce the day’s performers, and make announcements about the schedule.

“I felt like a reporter because every day I had to take notes, and then speak on those notes,” the comedian said.

“Even though the sailing was somewhat structured, there were sometimes changes when it came to the entertainment.”

He treated every performer he introduced with respect whether they were a schoolchild, or a world-class entertainer.

“Anyone performing at this event should get as many accolades as possible,” he said.

“If it was a class performing, I’d talk a little bit about the school and the ages of the children — I got that information from the teacher.

“I got to introduce Ne-Yo, Kes The Band and Wyclef Jean. Before going on, Wyclef told me he will run for president in Haiti. He said, ‘Don’t forget to mention that!’ He was serious. I missed Third World, which was a weekend show and I wasn’t working.”

He often went into the crowd to interview people, incorporating his unique brand of humour.

“I was given the freedom to be me,” he said.

“I wasn’t filtered. I already knew not to use profanity, which I don’t do much anyway. One day there were people from overseas in Bermuda for the first time because they followed the race. I was hooking up this lady with this guy because they were sitting next to each other. She said, ‘That’s not my husband’. I said, ‘You need to be sitting next to your husband.’”

Nadanja warned her that her actual spouse, who was sitting nearby watching, might disappear into the Bermuda Triangle.

“That was funny,” he said.

He also made short videos highlighting different aspects of the America’s Cup Village and the various events there each day.

“The camera followed me and they would show it on the big screen,” he said. “We called it ‘Where’s Nadanja?’ I would go into different places, such as to a tent that made home-made pizza.”

A segment filmed on the water put him totally out of his comfort zone. He has had a phobia since watching the movie Jaws when he was 8.

“They told me, ‘We need some footage of you on a boat’,” he said. “I was like, ‘Not me. I’m not going on a boat’.”

As it turned out, he loved it.

“I was on one of the boats that the Bermuda people sailed,” he said. “Heck no, the boat didn’t go very far out but it was cool. I was a sailor for the first time in my life. It was better than what I thought it would be.

“It was definitely cool to be with all these different people. I wish we could have another event there.”

Through it all, he continued to drive a taxi whenever he could. “They didn’t pay on a weekly basis, and they didn’t pay a lot,” he said. “I still had to make a living.”

• Nadanja Bailey’s next show, his annual birthday fundraiser, takes place at City Hall on September 15