From Shrimp Boat Sound to Hogfish: The Unconventional Story Behind the Bubba Look-Alike Showdown

Bobby & Michelle Mongelli (and grand daughter) with Jimmy Buffett [photo: Hogfish Bar & Grill]

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.

Front and back of the original Margaritaville Store rack card often seen in hotel, restaurant, and other lobbies that tourists frequent. [Provided by Chris Lauber]

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.

One might recognize the exterior of this building that honestly, hasn't changed much.

Now Square Grouper at 920 Caroline Street, the former PT's was a popular late night hangout.

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 Reefer 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.

Mac McAnally and J.L. Jamison dialing in for an anniversary show at the Hogfish Bar & Grill 

[photo: Bobby Mongelli]

 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.

One of Jimmy's last social media posts. [photo: Hogfish Bar & Grill]

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.

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That friendship is what inspired Bobby to create the first Bubba Look-Alike 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.

Jimmy Buffett playing with the Landshark Band on Duval Street in 1998. [photo: Gary Rowland]

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 and the Landsharks 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.

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.

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.

Duval Street Party: Need to Know

EVENT DETAILS

📅 Friday, September 4 ⏰ 5:30–9:00 PM 📍 200 Block of Duval Street, Key West

Gary and the Landsharks were the band that backed Jimmy Buffett during his surprise 1998 Duval Street performance. They’re returning to help recreate the spirit of that historic night in the place where it happened.

SCHEDULE

• 5:30 PM: Caleb Hogan opens with an acoustic set

• 6:30–7:15 PM: Bubba Look-Alike Showdown, presented by Hogfish Bar & Grill

• 7:30 PM: Gary and the Landsharks

• 9:00 PM: Street party concludes

ARRIVAL, ADMISSION & RESERVED AREA

This is a free outdoor street event. No ticket, event badge or check-in is required for general admission.

A small designated area near the front of the stage will be reserved for Ultimate Friend and Best Friend package holders. You must wear your Ultimate Friend or Best Friend badge to enter this area.

There is no separate viewing area for general souvenir Event Badge holders. All other guests may enjoy the event from the general-admission areas throughout the 200 block of Duval Street.

Space is first come, first served, so arrive early if you want to be closer to the stage. Note there are NO chairs available. If you bring chairs realize people will likely be standing in front of you blocking the view.

WHAT TO BRING/NOT TO BRING

• Comfortable shoes

• Light, weather-appropriate clothing

• Sunscreen and a hat

•  Please travel light and avoid bringing large bags

• Leave pets at home for this one. It will be hot, crowded and no place for relief

• No coolers or outside alcohol allowed

FOOD & DRINK

Event bars operated by Sloppy Joe’s, Irish Kevin’s and Rick’s will offer beverages for purchase. Outside alcohol is not permitted. All our partners also serve food inside their respective restaurants.

Please support these local partners, tip your servers, stay hydrated and never drink and drive.

WEATHER

The event is rain or shine unless conditions become unsafe. Schedule changes or weather updates will be shared through official Just a Few Friends channels and checking in through the QR code on your badge.

PARKING & TRANSPORTATION

Parking in Old Town is extremely limited. Walking, biking, taxis or rideshare are strongly recommended.

Duval Street will be closed to vehicle traffic within the event area, so allow additional time to reach the 200 block.

BUBBA LOOK-ALIKE SHOWDOWN

The contest runs from 6:30–7:15 PM. Contestants will compete for the Golden Coconut Trophy, a $1,000 cash prize and ultimate festival bragging rights. The judges will select three finalists, and the audience will choose the winner through live QR-code voting using the QR on your badge. Have your phone ready if you want to vote.

Break out your vintage Parrot Head gear and come ready to sing every word! 

The Duval Street Party is brought to you in part by Milagro Tequila, Sloppy Joe’s, Irish Kevin’s, Rick’s and the Monroe County Tourist Development Council. Please show them some love for helping us bring this celebration to Duval Street free of charge.

We’ll see you on Duval! 🌴🎶

🎶 Keep It Going at Hog’s Breath

The party doesn’t end when the Duval Street stage goes dark. Walk over to Hog’s Breath Saloon, 400 Front St., for the official after-party featuring Gulfstream from 8:30 PM to after midnight.

Admission is free, and no ticket or RSVP is required

DON'T MISS THIS: A Pirate Looks Back: The Key West Jimmy Buffett Tribute Show

📅 Daily · September 2–7 🕧 12:30–2:00 PM (Doors open at 12:00 PM) 📍 Comedy Key West · 218 Whitehead St. #5, Key West

There are plenty of places to grab lunch in Key West—but only one where you can spend it with a legend.

GET TICKETS

Watch your email for on-site merchandise pre-sale coming soon!

Order our limited edition items and pay online, pick up at Festival HQ!

2026 Just a Few Friends logo'd t-shirts in heather orange and heather sapphire | Engraved water bottles | Key West License Plates | Koozies | Festival Music Posters | Light up Leis | Just a Few Friends Stickers

 special charity contributions

Rare autographed collector sets of the Troubadour's Tour by JP "Gator" Wilson | Handmade Second Line Parade Parasols

 

“All events not affiliated with or endorsed by Jimmy Buffett’s Estate or Margaritaville Enterprises.”

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