First Bubba Look-Alike Showdown and Historic Landsharks Concert Coming to Duval Street Sept. 4

Free street celebration will introduce a new Key West tradition before Gary Roland and the Landsharks recreate the spirit of their legendary 1998 concert

KEY WEST, Fla. — The first Bubba Look-Alike Showdown, presented by Hogfish Bar & Grill, will take over the 200 block of Duval Street on Friday, Sept. 4, before Gary Roland and the Landsharks return to recreate the spirit of the legendary 1998 Meeting of the Minds street concert.
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Hosted in partnership with Sloppy Joe’s, Irish Kevin’s and Rick’s, the free outdoor celebration will run from 5:30 to 9 p.m. and bring together two tributes to Jimmy Buffett’s enduring connection to Key West: a new look-alike tradition inspired by one of his longtime local friends and a return to the Duval Street stage by the band that backed Buffett during one of the most memorable surprise appearances in Parrot Head history.

A Homage Rooted in Friendship

The Bubba Look-Alike Showdown was inspired by Hogfish Bar & Grill founder Bobby Mongelli, whose friendship with Buffett began more than 35 years ago.

Mongelli first entered Buffett’s Key West circle through Sunshine Smith, J.L. Jamison and the musicians working at Shrimp Boat Sound. The friendship continued through the late-night years at PT’s and, later, over seafood lunches at the picnic tables beside the shrimp boats at Hogfish.

Mongelli found inspiration for the contest in Key West’s Hemingway Look-Alike Contest and the way that tradition has introduced new generations to Ernest Hemingway. He believes a Jimmy Buffett look-alike event can do something similar—not simply by finding someone wearing the right mustache, sunglasses or flowered shirt, but by celebrating the many versions of Jimmy people remember.

Contestants may portray any age or era: the young musician who arrived in Key West in the early 1970s, the mustached pirate with a guitar, the barefoot island storyteller or the older troubadour who quietly returned to town, climbed onto his rusty red bicycle and revisited his old haunts.
Mongelli hopes the Showdown will grow into an annual Key West tradition celebrating the music, personality and sense of place Buffett shared with the world.

Local Buffett impersonator Caleb Hogan, creator of the daily tribute and cheeseburger show A Pirate’s Look Back, will open the program at approximately 5:30 p.m. and serve as emcee for the Showdown, which begins at 6:30 p.m.

Each contestant will introduce himself, pick up the guitar provided onstage and perform lip sync to a randomly selected Buffett song. A panel of local judges including Mongelli, Kit Carson (Sit With Kit), winner of last year’s Pencil Thin Mustache Contest and Tim Stockwell, 2024 Hemmingway look-alike champion, will narrow the field to three finalists before the Duval Street audience takes over and chooses the winner through live QR-code voting.

The first official Bubba will leave Duval Street with the Golden Coconut Trophy, ultimate festival bragging rights and a $1,000 cash prize. (register at www.justafewfriendskeywest.com)

Recreating a Legendary Duval Street Night

Following the Showdown, Gary Roland and the Landsharks will headline the evening with a concert honoring the night that forever connected the band to Jimmy Buffett and the Parrot Head world.

During the 1998 Meeting of the Minds convention, rumors once again traveled through Key West that “Jimmy’s in town.” That year, the whispers were true.

Buffett made a surprise appearance during the Landsharks’ Duval Street concert, stepped onstage with the band and turned the street into one enormous Key West sing-along. He famously told the crowd, “I told you I was here.”

Nearly three decades later, Gary Roland and the Landsharks will return to the Duval Street stage to recreate the energy and spirit of that historic performance. Gary will also be joined by special surprise guests for a concert that Buffett fans will not want to miss. Admission is free, standing only.

Food and beverages will be available for purchase from host bars Sloppy Joe’s, Irish Kevin’s and Rick’s. No outside coolers or alcoholic beverages are permitted.

The Duval Street celebration is part of Just a Few Friends Key West, held Sept. 3–7 to honor the life, music and Key West legacy of Jimmy Buffett.
More information: www.justafewfriendskeywest.com

Link to printable schedule: https://bit.ly/JAFF2026Schedule

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