The secret? Talent and timing made her a success in Key West’s thriving music scene

It’s nearing noon on a Sunday in downtown Key West and Elle Haley is running a little late.

Haley, a 22-year-old singer, has good reason.

She performed the previous night from to midnight at a Duval Street spot. Before that, she did a three-hour afternoon gig at a beach bar.

Now she’s headed to a place on Caroline Street where she will play her sixth gig in five days. Haley was able to leave her gear at the Duval Street bar overnight so she could pick it up on the way to her 1 to 4 p.m. slot.

She shows up dressed for the stage, and pulls off something that is so Key West: Haley loads her guitar and other stuff onto a small wagon that she hooks to her scooter before taking off down Duval Street.

The ride takes only a few minutes. But the image of Haley hauling her guitar by scooter is the perfect picture of a Key West performer doing what needs to be done to make it in the huge music scene on this tiny island.

“I’m waiting for the day it falls off,” she said of the wagon. “It works for now.”

Haley plays music for a living in Key West, a place teeming with musicians. It’s just her and an acoustic guitar on stage with the 100 or so songs she’s learned.

Many musicians here played professionally, fronting bands and touring, before they moved to the Southernmost City. Some studied music in college.

Not Haley. She was inspired to take up music as a career only after moving to Key West.

So far, it’s working out.

“For her age and just starting out, she’s hitting it hard very fast,” said musician Kari Wolf, a friend Haley considers a mentor. “She has a great heart and great personality and that will take her far.”

RockHouse Live in October was billing Haley as a “rising star,” and hasn’t stopped raving about her.

“Elle is a shining example of a gifted musician,” said Zach Bair, founder and managing partner of RockHouse Live. “She has the voice of an angel and we love her.”

Haley was a shy kid who played piano and considered music a hobby. She still can get stage fright. But she’s made a mark in a town that attracts a couple million tourists a year by singing cover songs for bar crowds. She hasn’t had a day job since early September.

“I never thought this would be my reality,” she said.

‘I was born in 1999’

That 1 to 4 p.m. gig Haley hauled her guitar to on her scooter is at Hank’s Hair of the Dog Saloon, which routinely offers live music from 1 p.m. to at least midnight every day.

Musicians play three-hour shifts, so there can be as many as four different acts a day. Haley is a daytime performer.

“She’s more polished and more professional than half the musicians on the island,” said Rob Benton, a musician who is a partner and the director of management and marketing at Hank’s. “She’s a natural at it.”

On the stage at Hank’s, facing a small crowd, Haley will sing the lyric, “Amie, what wanna do?” and play a not-so-depressing version of Tracy Chapman’s “Fast Car.”

She will kindly tell a customer she doesn’t know Elvis Costello’s “Alison,” and he takes it well.

A little girl walks to the stage to drop cash into the tip bucket, giving a thumbs up to Haley, who’s doing “Drops of Jupiter.”

At a show earlier in the week, Haley was at General Horseplay’s outdoor stage, turning out acoustic versions of the Cranberries’ “Zombie” and the All-American Rejects’ “Gives You Hell.”

She showed her age at one point during the show.

A man requests something by Smashing Pumpkins.

“I was born in 1999,” Haley replies, looking at the ‘90s music fan. She waits a beat.

“I know, that was the reaction I was looking for,” she said, before offering one from the same era.

“I can do Britney Spears,” she says, breaking into, “...Baby One More Time.”

‘A lot of talent’

Haley is a newcomer to Key West, arriving about eight months ago from her hometown, Westfield, New Jersey, where she grew up the third of four children. She shares an apartment in Key West with her sister.

In a short span, she’s become a regular performer with plenty of gigs to pay the bills, even on this expensive island. She went from watching her favorite musicians at bars to playing the same stages.

“I feel a little bit in disbelief that I’ve gotten to where I am so quickly,” she said in an interview, with a voice raspy from singing. “I thought I’d have to go door to door to convince people to take me. I’m pretty shocked that it all blew up.”

Haley moved to Key West without plans. She got a job serving at a downtown restaurant.

But a friend of the family, musician Jack Wolf, suggested she take up singing instead.

Other than spending a year in the high school chorus, Haley’s music experience was limited to getting up on stage with Wolf during vacations to Key West over the last few years.

“My mom told him I liked to sing,” Haley said. “I’d never done anything with it.”

On those trips down to the Keys, Wolf and Haley would sing “Shallow,” the duet made famous by Lady Gaga and Bradley Cooper.

“Just ‘Shallow,’ ” she said, laughing. “I got really sick of that song really quickly.”

“She was very green but I saw she had a lot of talent,” said Wolf, who is married to Kari Wolf.

At the time, Haley was terrified to be on stage alone. After a rendition of “Shallow,” Jack Wolf would ask if she wanted to do another song.

“I would say, I don’t have another song,” she said.

But he kept encouraging her.

“Every time I would come down here he would kind of force me a little bit into getting more comfortable on stage. Get rid of the stage fright.”

Wolf helped her get her first gig on Aug. 7. Her last day of waiting tables was Sept. 9.

“You’re going to make more money and have an overall better life if you play music,” Wolf said he told her.

Timing and luck

She had that one weekly gig at the Pier House, but when another one fell through she headed to Mallory Square, where she played for tips among the street performers and vendors six nights a week.

But it didn’t take long for other bars to book her. Bar managers would catch her show and get her name.

She filled in for a musician at Willie T’s and that led to a regular gig at a new Duval Street bar, RockHouse Live Key West, which needed musicians to fill the schedule, she said. Work began to add up.

“The timing worked out pretty well,” Haley said, adding that word of mouth also paid off. She also credits some good luck.

“ ‘Oh, there’s this new girl on the island, you should book her,’ ” Haley said.

Key West’s male-dominated music scene was another advantage.

“As you walk down the street all you hear are male voices and then you hear one female voice and your head kind of turns,” she said.

The idea of supporting herself by singing covers surprised Haley.

“Growing up you’re told musicians don’t make any money and here musicians kind of make one of the more decent livings for people in the bar scene,” she said.

“I still get shocked by places reaching out to me,” Haley said.

Before Key West became an option, Haley was in college. But she took a leave of absence before the pandemic began. She thought of working or traveling. Then COVID-19 hit.

“I was stuck inside for a year,” said Haley, who has a compromised immune system and had a liver transplant at age 13. Her father, Drew Haley, donated part of his liver, and the story was covered by the Jersey newspaper the Star-Ledger.

“I was quite literally doing nothing for a year,” she said, of her pre-Key West days. “I knew I didn’t want to go back to college. It was a whole lot of nothing trying to figure out what I wanted to do.”

She looked into internships in the music industry.

But she knew Key West. Her family visited often as she grew up. Her grandfather had lived here when her mother was in college. Her mother bought a house here about seven years ago. Haley decided to make the trip.

It’s one of the oldest stories in Key West: “I came here actually for vacation and ended up staying,” she said.

Haley said musicians here have been supportive.

“It’s welcoming and happy,” she said of the music scene. “There might be a few ups and downs to it but it’s really everything you would want to do as a musician.”

Living in the right now

Like most of her fellow musicians, Haley will play those aging pop songs that people three times her age can’t get enough of. But she tries to stay away from songs that she calls “too classic.”

Cue Neil Diamond’s “Sweet Caroline,” a singalong staple for bar crowds.

“It’s my hundred dollar song, so it makes me money,” she said. “Too many people ask for it, it’s kind of like ‘Freebird.’ I’ve never played ‘Freebird.’ But it’s kind of like that.”

No one has asked for “Margaritaville.” Yet.

“If you’re willing to put the work in and put yourself out there and try new things instead of playing “Sweet Caroline” for all the drunk tourists, that can make you stand out a little bit.”

Haley hasn’t mapped out the next few years. She sees herself eventually writing her own songs and traveling.

“I don’t really have any plans,” she said. “I’m kind of living in the right now so that in five years I can look back and be like, I had no idea what I was going to be doing five years ago.”

This story was originally published January 12, 2022 at 6:00 AM.

Gwen Filosa

Miami Herald

Gwen Filosa covers Key West and the Lower Florida Keys for FLKeysNews.com and the Miami Herald and lives in Key West. She was part of the staff at the New Orleans Times-Picayune that in 2005 won two Pulitzer Prizes for coverage of Hurricane Katrina. She graduated from Indiana University.