A new event, the Bubba Look-Alike Showdown, is set to debut on Duval Street, aiming to celebrate the enduring spirit and music of the late Jimmy Buffett. The contest is scheduled to take place on Friday, September 4, in the 200 block of Duval Street, running from 5:30 p.m. to 9 p.m.

Contest Inspired by Friendship and Local Tradition

The event was inspired by Bobby Mongelli, founder of Hogfish Bar Grill, whose friendship with Buffett spans over 35 years. Mongelli drew inspiration from Key West's Hemingway Look-Alike Contest, believing a similar event could introduce new generations to Buffett's legacy and the island he cherished. The organizers emphasize that the event is not affiliated with or endorsed by Jimmy Buffett’s estate or Margaritaville Enterprises.

Mongelli envisions the showdown as a way to honor the various personas of Buffett throughout his career, from his early days in Key West to his later years as a beloved troubadour. Contestants will have the opportunity to portray any era of Buffett's life, including the young musician of the early 1970s, the guitar-playing pirate, the barefoot island storyteller, or the elder statesman who quietly revisited his old haunts. The hope is for the showdown to evolve into an annual Key West tradition that celebrates Buffett's music, personality, and unique sense of place.

Event Details and Entertainment

Local impersonator Caleb Hogan, known for his daily tribute show “A Pirate’s Look Back,” will kick off the festivities around 5:30 p.m. as the master of ceremonies for the look-alike contest, which is slated to begin at 6:30 p.m. Participants in the contest will introduce themselves and lip-sync to a randomly selected Jimmy Buffett song using a provided guitar. A panel of local judges, including Mongelli, will select three finalists. The ultimate winner will be chosen by the Duval Street audience through live QR-code voting. The grand prize includes the Golden Coconut Trophy, festival bragging rights, and a $1,000 cash prize. Interested individuals can register for the contest at justafewfriendskeywest.com.

Tribute Concert to Recreate Historic Performance

Following the Bubba Look-Alike Showdown, Gary Roland and The Landsharks will perform a headline concert. This performance aims to recreate the energy of a memorable 1998 street concert during the Meeting of the Minds convention, when Jimmy Buffett made a surprise appearance and joined the band on stage. The spontaneous event turned into a massive sing-along, with Buffett famously announcing his presence to the crowd. Roland and The Landsharks will return to the Duval Street stage to evoke the spirit of that iconic night, and Roland is expected to be joined by surprise guests. Admission to the free outdoor celebration is standing room only. More details about the festival can be found in the Keys Weekly.