
Bill Hoebee’s radio career has spanned several decades, and his wildly irreverent “Hoebee in the Afternoon Experiment” program reaches several hundred thousand listeners each weekday. Yet if he hadn’t won a long-ago “Young Comedians” contest, earning prizes that included a radio show internship, he might never have found his on-air calling.
“I loved it,” Hoebee said of his introduction to the radio field. “I could immediately do the weird stuff, fake phone calls, fake commercials, song parodies and things like that.”
After growing up in New Jersey and experiencing the life-changing internship, Hoebee worked in Orlando radio. He arrived in Key West in 1991 to take a job at Florida Keys radio station WAIL 99.5.
“Key West was about as different as it could be from suburban New Jersey, and I made some friends right away,” he recalled. “I just felt like, being a weirdo my whole life, I was amongst my own.”
Though work later took him back to Orlando for a year, he couldn’t resist the pull of Key West. Following his return, he did morning radio for years before launching his snarky but good-hearted “Hoebee in the Afternoon Experiment” in 1998.
Still running 27 years later, the “experiment” proved to be an unqualified success. The show airs for five hours each weekday, broadcast to Keys listeners on WAIL 99.5 and Sun 103.1, and to audiences around the globe on iHeart Radio.
Its format features a blend of classic rock music, off-kilter accounts of Florida Keys escapades, and slightly deranged patter on virtually any topic — delivered by Hoebee and a regular cast of cohorts who include Carolyn Guarini, Scottish Joe and “voice guy” Tony Russell.
“I try never to bring in anybody who has any experience in radio or radio school,” Hoebee said. “That’s not us.”
“I mean, we don’t try to be professional!” he added, as though scandalized by the concept.

Despite refusing to admit it, the veteran radio personality is a consummate professional. He spends at least four hours preparing for each show, and zealously watches television news and other programs for scripting ideas. He has a comprehensive knowledge of demographics, market statistics and industry trends.
Perhaps equally important, he knows when to ignore trends — for example, when it comes to music selection for the show.
“In rock stations around America, they only play a list of 300 songs,” said Hoebee. “But I change every song they put in the lineup every day, and I take requests — and maybe two other people in America do that.”
Thirteen years ago, he even started a weekend show called “All Requests Saturday” where people from around the world e-mail in requests for him to play. Although he wasn’t sure it would last, it’s still going strong.
Hoebee’s success comes in part from knowing his listeners inside and out. He shares their demographic and age group, understands what they want to hear, and designs his program content to appeal specifically to their tastes.
“You can tell if something doesn’t work and you change it, but I’ve had to change very little over the years because I grew up with the listeners,” he said. “I feel like I’m one of them.”
The “Hoebee in the Afternoon Experiment” isn’t slick or overproduced; instead, it’s carefully crafted to seem spontaneous and uncontrived.
“I want it to sound like I just winged into the studio and let it rip — like I’m a regular guy who walked off the street into a studio, and was allowed to do a radio show and make people laugh,” Hoebee explained.
His “regular guy” persona and talent for fast-paced sarcastic patter also make him an in-demand host for concerts and festivals, both locally and elsewhere. He has introduced countless shows at the Key West Amphitheater, emcees multiple events during the annual Fantasy Fest celebration, has been a favorite “ringmaster” for spring break contests and many other Key West festivities, and gets calls from promoters around the United States to work their concerts and gigs.
Hoebee will also appear as (what else?) a radio deejay in two upcoming films whose details he can’t yet reveal.
Though he enjoys venturing into other performance realms, his true calling remains the radio field that helped shape his life and brought him a huge and devoted following.
“Everybody’s got a choice — they can either listen or turn the dial,” Hoebee said. “For the people that decide to stay there and listen, I want them to know I care about their entertainment … and I put in the work to give them that every day.”
