Jamaican Paul, Keeper of the “Groovy” Grove.

Homeless at times, stylish always, meet the 73-year-old boulevardier whose story — and staying power — have made him a village legend. 

In the mid-1980s, Paul Habib might have had a future in the clothing business. At Four Way Street, a hip boutique on Main Highway in the heart of Coconut Grove, store owner Billy Rudnick called his stylish clerk “a very good salesman. He had personality.” 

Bryn Ingram, who was a teenager when she began working with Habib at the store, says of him, “He’s got some sort of cool factor that people are drawn to.” 

These days, Habib is better known as Jamaican Paul – or, as some locals know him, Hollywood – a flamboyant backstreet boulevardier who may be one of the most photographed residents in Grove history and a living link to the village’s past as a quirky Bohemian enclave.

He still peddles clothing – black T-shirts bearing his face and the slogan “Come experience the groovy Grove.” But what Paul really sells is his friendly charisma and carefully-curated look. 

“I am who I am, a character,” says Paul on a recent weekday afternoon outside Barracuda Taphouse & Grill – a favorite haunt – on Fuller Street in Center Grove. 

As usual, he’s outfitted in a black jacket, red neckerchief, and his fingers and arms thick with silver bling.  Noticeably missing is his faded black beret that for years has portrayed an air of rumbled elegance. “What I do for a living is look good every day.” 

At 73, looking good every day is not easy, especially for someone who has drifted in and out of homelessness over the years, is chronically short of cash and acknowledges a long history with drugs and alcohol. Yet he manages. 

“I am here for a reason,” he says, his native Caribbean accent peeking through.

“I can’t tell people how to live, but I like to show them. You have to be happy, and smile, and be content even if you’re hurting.” 

Born in Kingston, the youngest of three children, Paul dropped out of high school and went to New York to study photography. “He was actually very good,” said his brother, Pierre Habib.

After a year or two in New York, Paul returned to Jamaica, and in 1977, when he was 26, emigrated to the U.S. with his father, a clothing manufacturer, and his siblings.

Paul worked at Four Way Street for about three years, and then, after a series of odd jobs, “He just wanted to not work anymore,” says Pierre.   

After years on the streets of the Grove, Paul eventually migrated across the Rickenbacker Causeway to Virginia Key and Jimbo’s, the funky, cheap-beer-and-smoked-fish redoubt where he was offered a bunk on a sailboat. There he hung out with the weekend partiers, hobnobbed with celebrities who showed up for film shoots and became something of an entertainer.  

Paul was dancing like a rock star long before Maroon 5 released “Moves Like Jagger” in 2010.

When Jimbo’s closed in 2012, Paul returned to the Grove, finding space on the boats of friends anchored offshore or sleeping in Peacock Park. He now has an apartment off of Grand Avenue, where he lives with his dog, Titi. His brother, a fitness trainer in Kendall, helps with the rent. 

Paul says he has had a couple of serious girlfriends, but never married and has no children. 

“Paul is a charming person, a heck of a personality,” Pierre Habib says.  “He didn’t want to be tied down. He just likes his free-spirited thing. He grew up in the 60s, and a lot of people are still living there, including him.” 

Jamaican Paul now spends many days in or around Barracuda, where bar owner Lee Kessler admits that he is both charmed and at times exasperated by Paul.

“I have known him for 30 years,” says Kessler. “Basically, he hangs outside. I have told him, ‘Paul, I don’t want you to approach the tables.’ He respects that.  And I respect the hustle. 

“He’s a really photogenic guy, with a personality that is unique,” said Kessler. “Look in his blue eyes and there’s life in there, a spark.” 

About a dozen years ago, one of Paul’s many fans created a Facebook page where those who run into him on the street can post selfies with him.  

“A FB page for Jamaican Paul, from Jimbo’s! Have you seen him recently? Buy him a beer and say hi,” the administrator wrote.

He also has an Instagram account (@jamaicanpaul): “Jamaican Paul / Mr. Hollywood

Local Grove celeb from Jimbo’s. Official Instagram. DM, tag, or hashtag #JamaicanPaul – if you see me, donations welcome!”

Asked what he sees as his future, Paul does not hesitate: 

“Keep moving. Don’t die.”