08/25/2026
𝐅𝐫𝐨𝐦 𝐒𝐡𝐫𝐢𝐦𝐩 𝐁𝐨𝐚𝐭 𝐒𝐨𝐮𝐧𝐝 𝐭𝐨 𝐇𝐨𝐠𝐟𝐢𝐬𝐡: 𝐓𝐡𝐞 𝐔𝐧𝐜𝐨𝐧𝐯𝐞𝐧𝐭𝐢𝐨𝐧𝐚𝐥 𝐒𝐭𝐨𝐫𝐲 𝐁𝐞𝐡𝐢𝐧𝐝 𝐭𝐡𝐞 𝐁𝐮𝐛𝐛𝐚 𝐋𝐨𝐨𝐤-𝐀𝐥𝐢𝐤𝐞 𝐒𝐡𝐨𝐰𝐝𝐨𝐰𝐧
The story behind Key West’s first Bubba Look-Alike Showdown begins decades before the birth of the Hogfish Bar & Grill —with a small gift shop at the Historic Seaport, a side landscaping business and a chance introduction that brought Bobby Mongelli into Jimmy Buffett’s world.
In the mid-1980s, Bobby was bartending at Turtle Kraals (now the Boat House), then owned by Paul Tripp, who also owned the Half Shell Raw Bar. In the building next door to the Turtle Kraals was Gifts on the Half Shell. By this time, Jimmy had found commercial success but continued returning to his Key West roots. He convinced Paul to let him use the building to open the first Margaritaville Store with his longtime associate Sunshine Smith. The little shack of a building at the end of Margaret Street also housed a cubbyhole office space blocked off behind the store itself, occupied by Sunshine, store manager Lori McLaughlin and Carol Shaughnessy, crafter of the early Coconut Telegraph fan newsletter.
Bobby was friends with Sunshine, and she knew he ran a small landscaping business on the side. By then, Jimmy had purchased his home on Sunrise Drive. The property had a second house next door where the band stayed, and Jimmy needed someone discreet and dependable to help care for the grounds. Sunshine recommended Bobby.
One day while Bobby was working at the property, Charlie—Jimmy’s original guitar and sound technician—pulled up with a young J.L. Jamison, who had just been brought to Key West to run Jimmy’s Shrimp Boat Sound recording studio. As Bobby remembers it, Charlie handed him a couple of joints and a bottle of tequila and told him to take the rest of the day off and show J.L. around town.
It was an unmistakably Key West introduction—and the beginning of a friendship with J.L., Jimmy and the band that would help shape the rest of Bobby’s life.
𝐄𝐧𝐭𝐞𝐫 𝐏𝐓'𝐬 𝐋𝐚𝐭𝐞 𝐍𝐢𝐠𝐡𝐭
Sometime later, following a falling-out between Paul and Jimmy, Bobby was offered a job at Margaritaville. Paul did not want him to take it, so he made Bobby another offer: take over PT’s Late Night.
Bobby initially resisted. PT’s had become run-down, and he was not convinced he wanted the responsibility. Paul sweetened the deal by handing him the keys, the liquor license and six months without rent.
In a roundabout way, Bobby says, his connection to Jimmy gave him his start in the bar business.
Bobby transformed PT’s into a true local institution—one of Key West’s great late-night gathering places. It stayed open until 5 in the morning, drawing the island’s full cast of after-hours characters: bartenders coming off their shifts, fishermen returning from days at sea, writers, pirates and assorted Key West night owls.
When recording sessions at Shrimp Boat Sound ended at one or two in the morning, J.L., members of the Coral Re**er Band or whoever else happened to be recording in Key West, would head to PT’s for dinner, drinks and a few more hours together. J.L. came in. The band came in. Jimmy came in. Writer Shel Silverstein came in. Long after the rest of Key West had gone home, PT’s was where everyone gathered for good food and the latest of nightcaps.
PT’s became so successful that Bobby could no longer keep up with both the bar and his landscaping work. He turned the landscaping business over to his brother and became a full-time restaurateur, setting the course that would eventually lead him and wife Michelle to Stock Island and the Hogfish Bar & Grill, and later Roostica Wood-Fire Pizzeria.
During those early years, Jimmy sometimes made tuna fish salad sandwiches for Bobby and his brother at the Sunrise Drive house. They shot baskets on the small concrete court Jimmy built there, and Jimmy sometimes gave them his season tickets for Miami Heat games. Bobby remembers never knowing who might be sitting nearby—Don Shula, Magic Johnson or Larry Bird, among other greats.
By the 1990s, Jimmy’s fame had reached another level and life around the Sunrise Drive houses changed. In 1998, after it served for about 15 years as a vacation home and crash pad for visiting artists, Buffett sold the property. Meanwhile, Bobby was busy building his own career, but the friendships remained.
In 2002, Bobby & Michelle opened Hogfish Bar & Grill on the Stock Island working waterfront. When Jimmy returned to Key West, the Mongellis would get a call letting them know he was in town and coming over for a meal.
“Jimmy loved seafood. He was a shrimp guy—loved ’em head-on,” Bobby remembers. “I’d go down to the shrimp boats and get fresh shrimp, hogfish or grouper—whatever he wanted—and then we’d sit down at these same picnic tables, catch up and have lunch.”
J.L. also introduced Bobby to Mac McAnally, beginning another lasting friendship. Mac has performed at Hogfish several times celebrating milestone anniversaries, and Bobby has welcomed members of the band, their families and visiting musicians with the kind of fresh seafood spread that comes naturally when your restaurant sits beside a working fishing fleet.
Through all those years, Hogfish remained the sort of place Jimmy seemed to have liked best—casual, local and real.
In February 2023, Buffett kicked off his "Second Wind Tour" with two intimate, surprise concerts at the Key West Theater for locals, in addition to the two planned Amphitheater shows. While in town, he bypassed the mainstream spots and spent his free afternoon at Hogfish Bar & Grill with Bobby and Michelle. The photograph taken that day—Jimmy in his sun hat and sunglasses, seated at one of the familiar picnic tables—has since become one of the most recognized images from his final months.
That friendship is what inspired Bobby to create the first Bubba Look Alike Contest Showdown.
The idea came to him while thinking about Key West’s famous Hemingway Look-Alike Contest. Bobby saw how that tradition had introduced new generations to Ernest Hemingway and believed a Jimmy Buffett contest could do something similar—not simply by finding someone with the right mustache, sunglasses or flowered shirt, but by celebrating the many versions of Jimmy people remember.
There was the young musician who arrived in Key West in the early 1970s with Jerry Jeff Walker and landed at the Chart Room, the mustached pirate with a guitar, the barefoot island storyteller who visited Key West to perform in the streets and the older troubadour who always seemed most at home when he slipped quietly back into town, got on his rusty red bicycle and visited his old haunts.
𝐅𝐫𝐞𝐞 𝐃𝐮𝐯𝐚𝐥 𝐒𝐭𝐫𝐞𝐞𝐭 𝐏𝐚𝐫𝐭𝐲
On Friday, September 4, that idea will take the stage on the 200 block of Duval Street during the recreation of the legendary 1998 Meeting of the Minds concert.
That street concert began as a performance by Gary Roland and the Landsharks Jimmy Buffett Tribute Band. Every year at the Meeting of the Minds convention of Buffett’s “Parrot Head” fans, it was whispered down the alley: “Jimmy’s in town.” “I hear Jimmy’s in town.” But this time, it was true. Jimmy made a surprise appearance and joined the Landsharks onstage as Duval Street erupted into one enormous Key West sing-along. He famously told the crowd, “I heard I was in town.”
Nearly three decades later, Gary and the Landsharks are returning to recreate the spirit of the night that forever connected them to Jimmy and the Parrot Head world.
Before that historic free concert takes over Duval Street, however, the stage will transform for the first Bubba Look-Alike Showdown, presented by Hogfish Bar & Grill.
The event starts at 5:30 p.m. with Caleb Hogan, a local Buffett impersonator and creator of the daily tribute and cheeseburger show A Pirate’s Look Back. Then, beginning at 6:30 p.m., contestants representing Jimmy any age or era will step into the spotlight. Caleb will emcee as each look-alike introduces himself, picks up the guitar provided onstage and lip sync performs to a randomly selected Buffett song.
A panel of local judges will narrow the field, and then the Duval Street audience will take over, choosing the winner through live QR-code voting. The first official Bubba will leave with the Golden Coconut Trophy, ultimate festival bragging rights and a $1,000 cash prize.
But Bobby sees the contest as something larger than a costume competition. He hopes it will grow into a Key West tradition that celebrates the music, personality and sense of place Jimmy shared with the world—and keeps that story alive for people who were not here to experience those early days themselves.
𝐋𝐮𝐧𝐜𝐡 𝐋𝐢𝐤𝐞 𝐚 𝐋𝐨𝐜𝐚𝐥
The story continues Saturday, September 5, when everyone is invited to cross over to Stock Island for Lunch Like a Local at Hogfish Bar & Grill from 11 a.m. to 1 p.m. The Bubba Look-Alike winner is expected to be there for photographs, along with live music and Bobby sharing stories from more than 35 years of friendship. Visitors can see where that famous final Key West photograph was taken and order the food Jimmy enjoyed there, including fresh local seafood, the world-famous Hogfish Sandwich and Jimmy (Weekley – IYKYK) Key West Cheeseburger in Paradise (which you can also sample at the Cheese Burger Beach Battle and Tribute Concert).
Another fun fact: the film The Beach Bum, featuring Jimmy Buffett as himself along with Matthew McConaughey and Snoop Dogg, shot several scenes at Hogfish and along the docks at Safe Harbor. While you’re there, be sure to take some time to walk around the working waterfront and see another side of Key West’s history.
𝐖𝐡𝐞𝐫𝐞 𝐭𝐡𝐞 𝐒𝐭𝐨𝐫𝐲 𝐂𝐨𝐦𝐞𝐬 𝐅𝐮𝐥𝐥 𝐂𝐢𝐫𝐜𝐥𝐞
Friday night brings back the excitement of Jimmy Buffett stepping onto a stage on Duval Street. Saturday afternoon brings the story back to a picnic table beside the shrimp boats, where two old friends could still sit down, have lunch and talk about the way Key West used to be.
Together, the two gatherings tell a much bigger story—one that began at Turtle Kraals and Gifts on the Half Shell, continued at the Sunrise Drive band house, carried through the late nights at PT’s and Shrimp Boat Sound, and eventually found its way to the working waterfront at Hogfish.
It is a story about music, Key West and the friendships that remained long after the last song ended.
