Ernest Hemingway is survived as much by his macho mythology as he is by his writing. Hemingway was in two plane crashes in two days. Hemingway shot himself in both legs while wrangling a shark. Hemingway had at least nine major concussions – and four wives. He had brain damage. He won the Pulitzer and the Nobel prize. He hunted and fished and wrote plays and books and articles and stories, for ever in pursuit of the truest sentence. He was rageful, charming, violent, brilliant and drunk.

Hemingway is also something of a Key West mascot, especially for a week every July, when a festival called Hemingway Days, which coincides with his birthday (this year, he would be 122) honours his legacy by gathering his lookalikes together.

A portrait of Ernest Hemingway seen inside the Hemingway Home and Museum located in Key West, Florida on July 24, 2021.

Weaving through the drunken, sunburnt revellers who pack Duval Street, it can be hard to picture Key West as Hemingway experienced it in the 1920s and 1930s: a sleepy tropical escape. “It’s the best place I’ve ever been anytime, anywhere,” the author wrote in a letter about the southern isle, where he penned many of his most famous work, including Death in the Afternoon and To Have and Have Not.

“Ernest was recognisable on the Key West streets: a big, handsome man, usually in very casual clothes,” Mary V Dearborn writes in her Hemingway biography. “In fact, he almost always wore shorts, using a knotted rope for a belt. On his feet, he wore Indian moccasins.” As he aged, he grew a white beard and paunch giving way to the “Papa” look – and if you have ever seen the 1957 portrait of Hemingway in a fisherman’s turtleneck, you can picture it perfectly.

People take pictures with participants of the Hemingway look-a-like contest

That is the version of Hemingway which most of the contestants at the lookalike contest – this year, there were 137 – aim to emulate.

The contest, which this year celebrated 40 years, is held at Hemingway’s favourite Key West watering hole, Sloppy Joe’s, and is fuelled by the myth of the man as much as by the growing myth of the contest.

“There was an arm-wrestling competition until some kid off a cruise ship got a compound fracture,” a T-shirt seller tells me, even while the event’s website says any arm-wrestling was forbidden because of Covid. “They keep ambulances on stand-by in case the old men pass out in the heat,” says a waitress, even though I didn’t see any. Covid cancelled last year’s events, but this year contestants told me they were vaccinated, that precautions were being taken, that they were not worried.

Collin Cope, participant in the Ernest Hemingway look-a-like contest

The very first lookalike contest was held in 1981 and organised by the then-manager of Sloppy Joe’s, Michael Walton. He dreamed it up as a way to attract tourists to Key West in the sweltering summer off-season. There were 36 contestants, and Hemingway’s brother Leicester was a judge.

These days, a rather official Hemingway Look-Alike Society exists; their article 1 bylaw states, “Have fun.” At the heart of the Society are the Papas, the previous lookalike winners, who form a brotherhood of white-haired men. Together, they raise money for the Hemingway lookalike scholarship which has given away hundreds of thousands of dollars, mostly to students attending the College of the Florida Keys.

Chris Storm, participant in the Ernest Hemingway lookalike contest

The competitors in the contest are known as “Wannabes”, and they come year after year from all over the world (one Wannabe I spoke with was there for his 27th time – he still didn’t win). Right now, including this year’s winner Zach Taylor, there are 14 Papas total. “Unfortunately, we’re all in the age category that we’re subject to circling the drain, so to speak,” says Papa Stephen Terry, the 2013 winner. “We have a few casualties every year.”

The Wannabes come in their Hemingway best, including some turtlenecks in the Florida heat, and sing songs, recite poems or give short speeches about why they, too, should enter the Papa ranks. Cheer sections spring up in the crowd.

“You look for someone that looks like Hemingway,” Papa Joe Maxey, who won in 2019, tells me wryly. “I’m looking for somebody to drink a beer with the rest of my life.”

A portrait of Joe Maxey, who won in the 2019 competition
Wally Collins, who won the competition in 2014

  • From left: Papa Joe Maxey, who won in the 2019 competition, and Papa Wally Collins, the 2014 winner.

Of course, there is a “running” of the bulls, which is more like a rowdy walk around the block. “It’s the most fun you can have with your clothes on,” Papa Wally Collins, who won in 2014, says. “It’s not just a bunch of grab-asses. It’s a bunch of good guys who have a good heart.”

For those who enter expecting a contest that is traditionally fair, this is not it. “They said if Hemingway came, he wouldn’t win the first three years. You have to show longevity and what you can bring to the scholarship fund, and people get to know you and your personality,” says the 2018 winner, Papa Michael Groover, who is married to the celebrity chef Paula Deen. (It took Papa Michael eight years to become a Papa.)

“It is a fraternity,” Papa Wally says. “You don’t want a guy to win it just because he looks like Hemingway. You want an adventurous guy – we’ve all done adventurous stuff. I’ve gone around the world twice, I was in the war, I’ve done all kinds of fun stuff, and was attuned to Hemingway’s idea of masculinity and heroics.”

Masculinity is, of course, a loaded word. The Papas and Wannabes I spoke with all said they admired Hemingway for what they considered to be his – his fishing and hunting, his ability to test himself, his daring travels, his love of women and rum. “A lot of people think he was a real a-hole,” Papa Matt Gineo, who won in 2011, says. “But I like his style.”

Matt Gineo, who won the competition in 2011
Dusty Rhodes, who attended this year’s competition

The thing that’s perhaps talked about the least at the lookalike contest is Hemingway’s actual writing. When asked, everyone says they have read him – some in school, others as adults, and a few have become amateur scholars thanks to their lookalike participation. But what is clear here is that the myth of Hemingway far overshadows his work.

In fact, others come to Key West for … the cats. “We notice a lot more people come here for them,” says Andrew Morawski, director of the Ernest Hemingway Home and Museum. He is referencing the 60 cats on site, all descendants of Hemingway’s Snow White, a polydactyl feline (meaning he had six toes). Many of his heirs are also blessed with extra toes. “Hemingway’s name isn’t mentioned any more,” Morawski adds. “Unless you really major in literature or some type of English degree in college, you don’t hear the name Ernest Hemingway.”

A portrait of Ernest Hemingway seen inside the Hemingway Home and Museum located in Key West, Florida

In much the same way as the cat lovers, the Papas and Wannabes descend on Key West just for the camaraderie and fun. Many are far older than Hemingway was when he died at 61, and I wonder what the man would think were he to enter his favourite bar and see all these men pretending to be him in the place he loved best. “He would teeter on that line of I love it and I hate it,” Morawski hypothesises.

But Jon Auvil, a multi-year finalist notes: “If I were Hemingway – and I would like to be Hemingway – I would be very honoured. However, this has outgrown him … It’s an institution.”