Billy Flanigan: The Happiest Man on Earth

A man who's spent his entire career performing in Disney World stage shows may not seem like a prime candidate for a documentary. But sometimes the purest stories are the most compelling.

I’ve no doubt you’ve never heard of Billy Flanigan. I hadn’t either. He is in many ways an unremarkable guy — a song-and-dance man who didn’t make his mark on big Broadway stages or in film musicals, but as a stage performer at Disney theme parks in Orlando. On the grand showbiz ladder, it’s a decidedly lower rung.

I grew up in O’do and knew plenty of people who worked in the bowels of the Magic Kingdom, which later expanded to include Epcot, the Animal Kingdom and other attractions. Despite the magical facade the company put on, it was very much a job like any other, with the usual accompanying gripes and letdowns. Still, people often stuck around a long time, few longer than Flanigan, who is now in his early 60s and has more than 40 years of consecutive one-year contracts to perform.

So what makes Flanigan such a compelling subject for a documentary is the absolute purity of his commitment to making others happy. He’s someone who’s sacrificed large portions of his life, even forsaking his own identity for decades, to bring a smile to audiences and to his own family.

When COVID struck and Disney shut down along with nearly all other entertainment venues, Flanigan took it upon himself to cheer up his fellow furloughed performers. This took the form of riding his bike to their house — even if they lived 20, 30, 40 miles away — and performing a little song-and-dance greeting that’s so goofy and corny and over-the-top ridiculous, people just couldn’t help breaking into smiles.

Someone soon dubbed these “Flanigrams,” and he gained a little notoriety during the doldrums of pandemic. Thus the seeds were sown for “Billy Flanigan: The Happiest Man on Earth,” written and directed by Cullen Douglas.

It’s at once a supremely entertaining documentary that also surprises us with an enduring emotional heft that doesn’t reveal itself until the latter portions of the film.

Watching it I was reminded of the show “Ted Lasso,” which I came to rather late after it had already become a crowd-pleasing hit. I remember reading an article about it when it was breaking out offering the novelty of its simple premise: “What if a man was nice?”

Like Lasso, Flanigan is so thoroughly infused with a sense of decency and regard for the wellbeing of others, he seems almost quaint and even alien in these angry, angry times. I think as people have stewed in their own outrage for so many years now, we’ve all grown collectively tired of these smoldering feelings and instinctively yearn for something full of light and hope.

Which is not to say that Flanigan is perfect — niceness and perfection being two very different things. But as we’ll see, even when Flanigan brings himself to do things that he knows will bring others pain, he does so only out of a sense of the deepest need for self-preservation and expression of his own true self.

Grown up in the north, Flanigan came from a big Irish family and was immediately tagged as the effeminate kid who lived to be on stage and make others laugh. He was teased and taunted, beaten up and dismissed. We hear from an early teacher, Barbara Robers, whom Flanigan credits with saving his life by telling him he had to be himself.

Boy Flanigan threw himself into every kind of opportunity to sing and dance, eventually studying theater in college and starting a successful all-women (except him) lip-syncing group called the Copy Kittens. He tried out for Disney, and almost accepted a job with Busch Gardens before getting the nod.

Flanigan is a self-avowed attention hog, someone used to having the lead role and always being “on center” whenever he’s performing. But we also hear from dozens of colleagues who talk about how giving and supportive he was to his fellow cast members. Even with the spotlight always on him, Flanigan made sure others reflected in that light.

He married one if his Copy Kittens costars, Karen, having three sons who — disappointment galore! — all turned out to be jocks before finally having a dance-loving daughter. Through it all, Flanigan worked long hours in every kind of stage show Disney could dream up, often tied to their latest animated release like “Beauty and the Beast,” “The Little Mermaid” or what have you.

It meant many long days, nights and weekends of rehearsals and live performances. Flanigan recalls that in one of the early stretches in the 1980s, he only had six days off in an entire year.

Through it all, Flanigan was driven by a “desperate need to be normal,” even as he fought against the stereotype of a straight man with a wife and kids who loved to perform. Eventually, though, he found himself compelled to follow the feelings that had been gnawing at the back end of his soul for many years.

Tall, blond and square-jawed, Flanigan resembles a Disney prince made flesh, the years having somehow only made his startling looks more chiseled and agreeably crinkly. I don’t know about you, but nearly all the men I’ve encountered in life who are that good-looking have turned out to be miserable pricks. Flanigan is the rare sort whose inner beauty matches what’s on the outside.

The production consists largely of video meeting interviews with Flanigan’s far-flung friends and family, plus more polished in-person interviews with the subject, plenty of archival footage and some slick animation and illustrations.

The music by Rob Pottorf punctuates and accents the ongoing dialogue, and the tight editing of Jeremy Gilleece keeps things moving at a quick pace without an ounce of storytelling fat.

(Full disclosure: Gilleece is one of my oldest friends — old and dear enough that I’d tell him if his editing sucked.)

If Disney World really is the happiest place on Earth, then Flanigan is its in-house living legend and non-costumed mascot. “Billy Flanigan: The Happiest Man on Earth” is the unlikely story of a man who stayed in the one place where people are always coming and going, and made it a little brighter and better for everyone.

The film will be available for streaming rental/purchase and on DVD Oct. 7.