It’s like Ben Fagan took his reality television victory to heart. After absconding with $500,000 in booty from winning the 2009 reality game Pirate Master, he bought a scenic 28-acre compound in the mountains of San Salvador, Costa Rica. Purchased with his father and brother using Fagan’s reality TV winnings, it’s the Holy City singer-songwriter’s idyllic getaway from the American hustle and bustle, where he stays a month at a time, three or four times a year.

“It’s a different tempo of life down there, and I over-cram my life here in the States, so it’s such a sweet breath of fresh air to sit back, smoke every day, and have time to rest and take life slow,” Fagan says, two days back from his last visit. “All the same I can’t complain because I love my life in Charleston too.”

He manifests that love in the bubbly feel-good roots-jam of his new 12-song release, Freestyle Sessions II. It’s a more rigorously written and produced effort than 2011’s nine-song debut Freestyle Sessions.

“There has kind of been an evolution in how I have been writing my music, and I was in the middle of a transition when we recorded the last one,” he says. “In my brain these songs are like the older brother to the last CD so I wanted to keep them connected together.” The two Sessions will be released as one collection.

Fagan’s a relative newcomer to the guitar, only picking it up seriously after he turned 20. In 2007, months after graduating from the University of South Carolina with a double major in business administration and marketing management, Fagan was plucked as one of 16 contestants on the pirate-themed reality game show. He made off with the half-million dollar prize even though it was canceled midway through its run.

“If I wouldn’t have had Pirate Master, I probably would’ve had to get a semi-normal job. I’ve never had a normal job. I’ve always owned my own business, but I’d have had to work a lot more as opposed to work on music full-time,” he says.

Fagan played with his brother Chris in the Plainfield Project, a reggae-tinged groove rock sextet that won numerous local accolades during its five-year run before breaking up in 2010. The struggles of a democracy involving “six Kobe Bryants,” as he describes it, eventually overwhelmed them.

Now Chris is the first mate on a mega yacht, and Fagan’s leading a new band with his name out front. His new backing band, the Holy City Hooligans, are a loose cooperative of the ready, able, and willing.

That’s important because Fagan likes to take the band on tours of Costa Rica and the East and West coasts. They pay for those tours thanks to their very busy schedule as a wedding band, with over 40 dates booked for just the rest of this year. The wedding circuit pays not only for tours but for recording, as Fagan’s too business-savvy to dip into his principal. Instead he created something self-sustaining.

However, most of the time Fagan tours in a duo with drummer Quentin Ravenel.”We love having a horn section, and I love playing bass and singing with the full band, which is very different from playing guitar and doing all the loop stuff,” he says. “When we tour as a duo, it’s like a four- or five-piece because I use my loop machine to lay down 10 to 11 different layers spanning from beatbox to synth-bass to piano and synth leads to electric guitar and harmonies, like a hip-hop-reggae Keller Williams or Zach Deputy.”

Fagan displays his accelerating skills on the Freestyle Sessions II. He’s learned new instruments and showcases that felicitous experimentation, expanding upon the band’s island-life, rap-roots soul. Since the first LP, he believes his songwriting’s substantially improved.

“It’s less about subject and more about the style of creation in how I broach things,” he says. “I’ve now taught myself to play keyboards, and there’s a lot more synthesizer involved. In fact, one of the new tracks on my new CD I lay down everything that you hear.

“I did half with a full band, horn section, and all that stuff,” he continues. “The other half was just me going into the studio and laying down all the melody parts, all the basic rhythms except for drums and kind of creating it all from one source with Quentin, my main man, laying down drum tracks and harmonies.”

Half the album was recorded at Charleston Sound and the rest at Truphonic Recording Studios, with Truphonic owner/engineer Majeed Fick. “Majeed helped with some co-production because I had never recorded everything myself and that’s a lot for one dude,” Fagan says. “He gave me a bunch of extra time basically to make sure that we could really do it right, and he had some great ideas I was able to use.”

The positive, upbeat outlook he wants his music to express shines sharpest on “Fly High,” a track on which Fagan plays all the instruments. Ironically, it was the least well-formed when he went into the studio, yet now it’s the one of which he’s proudest.

“I didn’t have any of the verses written when I went into Truphonic. I just had the basic hook and basic melody,” he says. “I can put it on play and listen to it 50 times in a row and it just didn’t get old. The little trigger point in my chest kept going off. It’s just the most happy, positive, and a little edgy song I’ve ever written.”

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