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Exclusive: How Billy Flanigan Became the Happiest Man on Earth

Exclusive: How Billy Flanigan Became the Happiest Man on Earth

"Here's a gentleman who's had a lot of things that he's had to deal with, and yet he's overcome them. And he's done it with this incredible, selfless power that he has."

To celebrate the release of Disney's documentary Billy Flanigan: The Happiest Man on Earth, director Cullen Douglas recently sat down with Tracy E. Gilchrist of Advocate Today to discuss how one man can make the world a brighter place, despite the inner turmoil he's facing.

Billy Flanigan, subject of the film, made headlines during the height of the Covid-19 pandemic when he embarked on a cross-country journey to deliver "Flanigrams," socially-distanced, singing and dancing telegrams. On his quest, Flanigan biked over 7,000 miles, which viewers will get to directly witness in the film.

Director Cullen Douglas originally discovered Flanigan through former co-workers at Disney World, as Douglas used to be a performer and showrunner at the theme park. When old colleagues began to post about getting "Flanigrammed" on Facebook, Douglas' curiosity peaked.

"I just thought it was kind of an amazing thing," Douglas shares. "When I worked at Disney over 20 years ago, the name Billy Flanigan was already legend back then. He just sort of epitomized what I think Walt Disney would want in his parks. This bigger, larger than life, accessible performer. I had already been predisposed to what kind of magic Billy was capable of, but then seeing what he was doing when we were all locked down, and kind of scared, and not knowing what was gonna be happening next -- this small act of kindness that he was extending to folks really just gave me hope."

Flanigan's kindness inspired Douglas to make the film, as the director describes him as having "his own special brand of Pixie Dust." Despite this, Douglas was surprised to find that the performer was masking a rich personal life, and a decades-long struggle to come to terms with his sexuality.

"It reminded me of the times as a performer where I've had to leave things 'in the wings' and step out onto stage, because the audience is expecting a great show," Douglas says. "Whether I was dealing with my son's cancer fight, or anything else, the show had to go on. In talking and discovering more about Billy, he had lived so much of his life denying who he was, and with this internal turmoil. Yet out onstage, he was the man with the thousand-watt smile. But on the inside, he was really hurting because he couldn't be his true self."

Before he accepted himself as LGBTQ+, Flanigan fathered four children with his ex-wife. While his coming out put a strain on their relationships, Cullen shares that the documentary has begun the healing process for them, Billy especially.

Cullen is also excited for the healing this film could bring to others. As Flanigan has always been a private person, he wasn't too keen on sharing the intimate details of his personal life. According to Cullen, what finally changed Flanigan's view was the idea that his story could help reach struggling people.

"When Billy realized that his story was gonna be going out there, because he's been a private person for so many years and didn't share any of his personal stories with his coworkers, he realized that he was at the point where he could help. The film could perhaps reach someone like himself, who was seventeen years old and feeling lost and disillusioned. And if that could offer hope, it was sort of just a no-brainer for all of us," Douglas says.

To find out how Flanigan was able to make it through his hardships, viewers will have to tune in when Billy Flanigan: The Happiest Man on Earth begins streaming on Apple and Amazon. As for what Douglas thinks, he believes Flanigan has an incredible power.

He says: "Here's a gentleman who's had a lot of things that he's had to deal with, and yet he's overcome them. And he's done it with this incredible, selfless power that he has."

Catch The Advocate Channel 's full interview with Douglas below.

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Ryan Adamczeski

Digital Director

Ryan is the Digital Director of The Advocate Channel, and a graduate of New York University Tisch's Department of Dramatic Writing, with a focus in television writing and comedy. She is also a member of GALECA, the LGBTQ+ society of entertainment critics.

Ryan is the Digital Director of The Advocate Channel, and a graduate of New York University Tisch's Department of Dramatic Writing, with a focus in television writing and comedy. She is also a member of GALECA, the LGBTQ+ society of entertainment critics.