Bubba Look Alike Contest

Presented by Hogfish Bar & Grill

Friday Night · Duval Street Party · Just a Few Friends Festival

As part of the historic recreation of the 1998 Meeting of the Minds concert on Duval Street—featuring Gary & the Landsharks—the stage will turn into a search for the island’s best Bubba.

If you’ve ever been told you look like the troubadour — any age, any era — this is your moment.

The Bubba Look-Alike Showdown invites contestants to step into the spotlight and channel the look, attitude, and presence of Key West’s favorite son. Whether it’s the early pirate days, the mustached storyteller, or the laid-back island legend, we’re looking for the one who brings it to life best.

Hosted by local Jimmy look-alike and Comedy Club lunch show host Caleb Hogan, contestants will take the stage one by one, introduce themselves, and then pick up a guitar provided on stage. From there, a random, well-known Jimmy Buffett song will kick in—and it’s on. Each contestant will have to lip sync, perform, and embody the part in front of a live audience.

A panel of esteemed local representatives will narrow the field down to three finalists. From there, the crowd takes over—the winner will be decided by audience vote via QR code, making this a true people’s choice moment.

The champion will take home:

• $1,000 cash prize

• The Golden Coconut Trophy

• Festival bragging rights

Presented by Hogfish Bar & Grill, a true Stock Island institution and longtime favorite of Jimmy Buffett himself. Owner Bobby Mongelli, a close friend of Jimmy’s, helped create the kind of place Buffett loved most—unpretentious, local, and real. It’s also where one of his most iconic late-life Key West photos was taken, sitting at a picnic table, right at home.

Pre-registration is strongly encouraged to guarantee a spot.

Walk-up entries will only be accepted if space is available.

Think you’ve got what it takes?

Come prepared.