Go the Extra Smile: Billy Flanigan

During the pandemic, Billy Flanigan gained fame and followers with his traveling Flanigrams. Now, Billy is part of a new, exciting project to spread the joy even farther.

Story: Mark McWaters / Photos: Fred Lopez

Rarely do the words ‘COVID’ and ‘blessing’ share the same sentence. Yet, in the case of Billy Flanigan, the pairing could not be more apropos. Though he’s known to Winter Garden locals as the host of various charity events, the host of Open Mic Night at Pilar’s on Thursday nights, and an entertainer at Disney for four decades, the world at large may know Flanigan best for his Covid-inspired creation: The Flanigram.

It was in March 2020, two weeks or so into the lockdown, and Flanigan was going stir-crazy. “I’d already done everything around the house I could do that needed doing and I was going a little nuts,” he says. He is an active guy who bikes every day, and to get out of the house on that fateful day, he turned to his trusty two- wheeled friend.

“I was biking on the West Orange Trail near my house and I thought, if there’s someone I know who lives near the Trail, I’ll just bike on over and say hello!”

As it happened, Flanigan had a very dear friend, Hannah, who t the bill perfectly, so he biked over and knocked on her door. She opened it and he barely got “Hey! How are you?” out before she started bawling. She hadn’t seen anyone in two weeks, hadn’t communicated with anyone. So, they sat and “socially distant-chatted for a very long time.” He took pictures of them and afterward, posted on social media that they had visited. Hannah, coincidentally, did exactly the same thing. She wrote, “This guy knocked on my door. It was Billy Flanigan. We sat and talked. How wonderful it was for him to think of me!”

That was the post that started it all. Eventually, Flanigan would develop a song to accompany each official Flanigram, but that would take several tries for him to develop and perfect. They weren’t even called “Flanigrams” in the beginning—that moniker came later, courtesy of a friend— but the idea had begun taking root. And boy, did it!

He started following people who responded to Hannah’s messages. They were both cast members at Disney and shared a wide circle of friends. Friends and friends of friends started posting, “I got my visit from Flanigan today!” or, “Gee, I wish I could get a visit.” So, Flanigan made notes, planned routes, and o he’d go.

Oddly, for someone who’s made his way in show business for as long as he has, he gave absolutely no thought to a costume, or a “look.” He never took to wearing funny hats or decorating his bike with signs and streamers. “I wear a long-sleeved shirt, shorts, and my bike helmet … and a smile.”

So far, Flanigan has logged 562 Flanigrams over 16 states and 7,000 miles! That is a whole heck of a lot of cheer, covering a ton of territory. But when his accomplishment is pointed out, all Flanigan does is shrug his shoulders and grin.

“The message for me is that there really is no act of kindness too small. When you think about it, I’m riding my bike to a house, knocking on a door, and singing a song. It’s not brain surgery … I had no idea this thing would blow up like it has. Really, I needed this as much as everyone else. I’m a people person. I needed to see people and say hello.”

Billy Flanigan as a young boy—sporting his same million-dollar smile

Courtesy Billy Flanigan

Grin and Share It

Much as Flanigan downplays the impact of “this thing” he’s done, his Flanigram-ees have exactly the opposite impression. In fact, the first three he visited way back at the beginning—Hannah, Amy, and Katie—decided the whole world needed Flanigrams.

They took to social media and started a campaign, spreading the word about Flanigrams with the goal of getting Flanigan on "Some Good News" with John Krasinski. The first he heard about that was from his daughter who was scrolling Instagram at the time, when she said, “Hey, Dad. Look at this!”

Flanigrams have now been featured in "People Magazine" and on "Good Morning America." Flanigan appeared on "The Doctors," on Dr. Laura Schlessinger’s program "Dr. Laura," and “a ton of podcasts, radio interviews, and "Margaritaville" on Sirius XM,” he says, to name a few.

Although they didn’t quite reach "Some Good News," there is even better news on the horizon: a documentary titled Billy Flanigan—"The Happiest Man on Earth" is in final edit and soon will be making the rounds at film festivals.

A friend one day and said a producer in Atlanta was interested in his story and might want to do a documentary about Flanigan and his Flanigrams. After assuring him that she wasn’t kidding, she put Flanigan in touch with the producer. Flanigan stopped by the producer’s house one night on his way through Atlanta and Flanigrammed him. “He knew about me and my Flanigrams because we’d already talked,” Flanigan says. “But after it was over he said, ‘OK. Now I’m totally sold. Now I know what the big deal is.’”

A Million Tears

"The Happiest Man on Earth" documentary’s tagline is, “Behind Every Smile Are a Million Tears.” We couldn’t let that go by us without wanting to know more, could we?

Meet Flanigan for the rst time and you’ll probably be struck by one thing—that smile. He smiles a lot, in fact he smiles all the time. And you’d wind up thinking ‘The Happiest Man on Earth’ ts that man to a T. But people are rarely so simple.

Flanigan’s Flanigrams have taken him across 16 states. So far, he has biked over 7,000 miles and delivered 562 Flanigrams.

“I was the fth child of six, and you could say I grew up craving attention,” says Flanigan. “My dad was de nitely the happiest man on earth. He loved each day. He loved life. I got a lot of that from him.”

That desire for attention drew him to the performing arts. “Sixth grade was my very rst show, and I fell in love with the stage,” he says.

“I loved making people laugh, making them cry, and boy did I catch that bug. But this was the early 70s, when people like me weren’t cool. I got bullied a lot. Had beer bottles thrown at me when I was walking home with my guitar case.

Got shoved into lockers. I had one teacher who told me ‘they’re just jealous and they don’t know how to handle you.’ But the bullying really messed me up as a kid. Thank god there was no social media then.”

Despite the challenges, Flanigan nished high school and enrolled in the Boston Conservatory of Music for a bachelor of ne arts in musical theater. From there, he got a job at Walt Disney World. “I thought I’d do Disney for a year, then go on to try Broadway or Hollywood, wherever my BFA wanted me to go. But one year turned into 40 in a heartbeat. And here I am.”

Flanigan has four sons and is glad the same bullying he’d endured didn’t happen to them. “My boys are jocks, so good at sports—I have no idea where that came from—so I got involved where I could.” That involvement entailed singing the national anthem at their games, choreographing cheerleader routines, and announcing the games at West Orange High School. He was even the president of the West Orange PTO.

“I have always been happy, yes. But no one is happy all the time,” says Flanigan. One of the toughest challenges of his adult life was when his daughter, Lexi, was diagnosed with type 1 diabetes. “It was nine years ago, when she was 13 years old. I sat down and cried my eyes out. My sister—her aunt—died from that disease at 42 after su ering a stroke at age 38. Lexi thought her disease was a death sentence.”

All Flanigan could do was move forward, learning as much about type 1 diabetes as he could. Fortunately, the advances that have been made in the last decade have improved the outlook for patients considerably. He got involved with the Juvenile Diabetes Research Foundation, started hosting their events, singing the national anthem at charity walks, and involving his daughter and her friends.

He made sure Lexi became adept at managing her disease herself, something her mother had always done for her in the past. “It took about a year, a lot of arguments, a lot of ghting, but she learned. Now she knows how to order her insulin, her needles, her Dexcom. I’m so proud of her. She recently moved out with some girlfriends, and I’m con dent that she’ll be ne. She knows what to do, where her aunt, my sister, just guessed.”

The World Smiles With You

Will Flanigan ever hang up his helmet and give up the ‘gram? Has the easing of Covid restrictions changed the need for them?

“People still enjoy them. They still smile. But it has changed a little from people needing a Flanigram to wanting one,” he says. “They’ve heard about them and want to be included. I suppose I will stop them one day. Everything has to end, right? But not today.”

Is it possible that Flanigan is truly the happiest man on earth? Maybe. “I’ve always loved what I do for a living. My job is to make people happy, which makes me happy. Am I and my Flanigrams worth making a whole movie about for gosh sakes? I don’t know. I guess for that answer, you’ll have to see the movie.”

The First Flanigram

Hannah Laird was the very first person to receive one of Billy Flanigan’s “Flanigrams.” It couldn’t have come at a better time. “We were three or four weeks into COVID lockdown,” she says. “Disney was closed, everyone huddled at home, no contacts with friends, no interaction with people, period—and my doorbell rang. Who could it be? I didn’t order anything. Then I looked out the window and saw this neon green bicycle helmet and I knew!” •• Billy stayed on his bike and Hannah stayed on her porch and they just talked. It was exactly what the two friends of 15+ years needed. Billy said, “I was riding my bike and I figured I’d come say ‘Hi!’” •• They talked for several minutes, re-connecting, and afterward, Billy turned his bike around and rode away. Hannah shut the door and realized all at once what COVID had changed and how important real connection is. •• “I shut the door and started to cry.”