So Jimmy Buffett walks into a bar… This being Jimmy Buffett, the bar is on some remote corner of the map – in this case Cape Verde, the Portuguese archipelago off the coast of West Africa. Jimmy was touching down in his plane like Indiana Jones on his way from Puerto Rico to Bamako, Mali on the first part of a journey that would take him to Timbuktu, the Sahara Desert, Morocco, Ireland, and New York – an adventurer’s holiday. He was traveling with his longtime confederate Kino, Spock to Jimmy’s Kirk, and four other friends – including MTV godfather Tom Freston and music legend Chris Blackwell, the man who produced “The Harder They Come,” brought Bob Marley to the world, and whose Island Records gave a home to everyone from Cat Stevens to U2.

The travelers dropped their bags at a hotel and went off to look for food, liquor and music. They hit a few saloons and found great music everywhere. It was like Cape Verde was Beale Street, Memphis 1955 – everybody was a musician. But even in this player’s paradise, one young man stood out and knocked the world-weariness out of these music veterans. Ilo Ferreira was called onto the small stage at a local restaurant where everyone seemed to know everyone else. Ilo was young – looked like a college senior – and handsome. He showed quiet confidence as he picked up his guitar and adjusted his microphone. Then he started to play and sing and Buffett leaned forward.

Ilo had the high, beautiful voice of the young Sam Cooke, effortless charisma, and a natural grace on the guitar. He sang what sounded like an old soul classic none of the visitors could place. Turned out Ilo wrote it. With every song he played, the excitement of Jimmy’s crew grew. Where did this kid come from? Could he really be THIS good?

Now, when friends on vacation get together in a saloon to drink and gab, it’s pretty common for big plans to be laid and big promises to be made. Bar talk very rarely gets beyond the bar. That night, Jimmy talked with Ilo and his band, even his father, about how good the young man was. Jimmy’s companions imagined out loud bringing the kid to America and putting him in a real recording studio. Jimmy just asked Ilo if he would come to lunch the next day – and bring his guitar. Ilo said sure, and the next day the visitors asked him to play again – in the sober light of day. When he finished they were even more excited. Blackwell and Freston agreed – Ilo really was THAT good. Jimmy and Ilo exchanged emails and phone numbers and promised to keep in touch. Jimmy said to his friends, “I’d really love to bring this fella to America and give him a shot. He’s just great.”

Now, here is where Jimmy Buffett is different from everybody else in the music business. He didn’t forget that ambition when he got back to the States. He did not leave his enthusiasm behind when the plane took off. He stayed in touch with Ilo. He played a tape of Ilo’s songs to big time record executives and producers. Other people saw what Jimmy had seen on that island off the coast of Africa. The kid had IT. Jimmy arranged some studio time for Ilo in Nashville and hooked him up with a name producer who heard what Jimmy heard. Then Buffett got his big brainstorm.

The first two weekends in September he was playing his biggest headlining shows ever to just under 60 thousand people a night at the New England Patriot’s stadium outside of Boston. What if he brought Ilo over and put him on the show? How would it be for a young singer from Cape Verde to step out on stage with the Coral Reefer Band behind him and 60 thousand Parrot Heads in front of him? It would sure be a test of fire. If Ilo could get through that initiation, he really could become what Jimmy glimpsed for him.

The airline lost Ilo’s clothes between Cape Verde and Boston. Ilo just smiled and said it was fine. He was good in t-shirt and jeans. Ilo was unflappable. Rehearsing with Jimmy and the band, he was open, quick to learn and a sharp listener. He did not seem to have any nerves about his big premiere. On the day of his US debut he climbed into the back seat of one of the vans caravanning from Boston to the stadium and promptly fell asleep. The kid was beyond cool. He had the confidence of a pro. If anything looks bigger than a football stadium packed with fans, it’s a football stadium when it’s empty. Ilo wandered out of the van and into the empty arena. He said, “It’s really big,” as casually as a man looking at an elephant.

Jimmy called him up to soundcheck. Jimmy’s stage was about twice the size of the restaurant where Ilo played on Cape Verde. Would the kid be able to fill the space? That was a trick it took some performers years to learn. The road crew fitted tiny monitors into Ilo’s ears. Jimmy started leading the band through one of Ilo’s songs. Ilo swung his guitar behind his back like Johnny Cash, planted his feet like Bruce Springsteen, threw his head back and sang like Marvin Gaye. Buffett just laughed. No problem.

Six hours later, after dark and half way through an ecstatic show, Jimmy told the crowd about meeting Ilo in Cape Verde and then asked his young friend to come out on stage. Ilo sang with Jimmy on a Buffett song, “My First Look,” and then – to the surprise of the audience – stepped to the mike and did one of his own – “Let Me Love You” – while Jimmy slipped into the backing band. Women down front were dancing and waving at the charismatic stranger. Everybody got it. Ilo smiled, bowed and moved off-stage – where he studied the rest of the show from the wings like a talented young athlete watching an all star.

Moments after singing to more people than he had ever seen in one place in his life, Ilo had demeanor of someone who knew he could go all the way, and was patient to figure out the requirements. After the concert, Jimmy Buffett was jubilant. “How about Ilo?” he kept asking everyone. “He really pulled it off!” Newspapers covering the concert wondered about the talented young singer Buffett had brought over from somewhere off the coast of Africa. What would happen next with the mysterious Ilo?

Ilo was on his way back to Cape Verde, with a ticket to meet Jimmy in Nashville in October. Time to get the kid in the studio. He played his first American show to sixty thousand people and acted as cool as if he were singing for his friends in a small room back home. Stardom is a mysterious thing – some people who deserve it never get it and some who don’t seem to become famous anyway. You can never say for sure that someone is going to become a star. But talent, that’s something different. Talent makes itself known. Thanks to the guy who walked into the bar, Ilo Ferreira’s talent was about to make itself undeniable.