Every Dog Has Its Day at Sloppy Joe’s

After a successful Top Cat run last winter during National Feline Lovers Month, which raised over $10K, Sloppy Joe's Bar is back this summer to celebrate all the dogs while raising money for its charitable foundation.

Sloppy Joe's CEO Jeff Allen, himself a dog lover, first floated the possibility of balancing last year's fundraising with a canine version. The result is this summer's Top Dog Contest.

This year’s grand-prize winner will receive a “Roscoe Award,” a gift certificate from American Dog Outfitters, become a featured face of the contest throughout 2027 and, perhaps most appealingly, have their name permanently displayed on the Top Dog Plaque inside the iconic bar.

That puts one lucky pooch in some pretty distinguished company. Sloppy Joe’s walls already feature decades of Key West history, including the faces of victorious Papas from Hemingway Days’ nationally covered Look-Alike Contest.

Roscoe, in this case, was the beloved dog of longtime Sloppy Joe’s patrons Karyn and Dave. There is even a dedicated barstool on site allowing Roscoe to live on as part of the annual award.

Dog owners can sign up in a few minutes through the Sloppy Joe's Foundation website, where they can submit photos, video, and a brief bio of their pooch. Contestants will then appear on the website throughout August where the public can view their profiles and vote.

Voting is done with your pocketbook with all proceeds benefitting the foundation and its work to fund a wide array of local nonprofits plus scholarships and musical opportunities for future generations. One dollar equals one vote, with discounts available for higher vote purchases.

During this time, Lucky One Lemonade will also donate $1 to the Sloppy Joe's Foundation for every Lucky One Lemonade sold at Sloppy Joe's each Saturday in August.

Paul Goodale, Sloppy Joe's entertainment and technology manager, grew up with fond memories of his Cairn Terrier named Velvet before falling in love with cats. To him, this event feels on brand for a community that doesn't blink at parrots and reptiles paraded down Duval, cat whisperers holding court at Mallory Square or the increasingly common site of pets downtown at all hours of the day.

"Our whole one human family and the whole island as a community speaks to why people are such pet lovers down here. They just totally fine with giving and making sure other people have a good life."

Even other bars, including Bearded Lady, are paying tribute to dogs with their own competition. Key West seems to recognize the tenacity of pooches sticking by our sides, year-round, including the stretch of intense summer months.

Voting opened on August 1 and will remain open through the final hours of August 31, after which the victorious dog will be announced online.

Given that dogs are a bit easier to wrangle than cats, as the bar learned last year, keep an eye on a possible appearance by the top dog on the bar's patio on Greene Street.

The winner might want to see just how real that bone-shaped plaque is, after all.