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Billy Flanigan: The Happiest Man on Earth

“The Happiest Man On Earth” Gives Away Christmas Trees To Families In Need


Windermere, FL: Billy Flanigan, who is the longest consecutively-contracted entertainer with over 40 years of performing in Disney World stage shows, is giving away Christmas trees to families in need in Central Florida. Billy owns Santa’s Old Fashioned Christmas Tree farm and gives the proceeds to Windermere High School’s Chorus Program every year. The donations to Windermere High School help the chorus program get to participate in all of their events.


Billy is taking it one step further this holiday season, and giving away trees from his lot to families who otherwise would not be able to afford them. So far, he has donated 13 trees to families attending a local church in Clermont, Florida.


“My favorite part about owning a Christmas tree lot is that at the end of the season when I have trees left over, I like to donate them to a good cause or a friend or family that might go without,” said Flanigan.


A family came to get a tree and they had two little girls and the mom told me that it was her little girls’ wish to get a Christmas tree this year and they didn’t think they were going to be able to get one, so we made that happen,” Flanigan said, with tears in his eyes.


According to AARP,  “Bah, Humbug: Inflation Drives Christmas Tree Prices Up”, buyers can expect a 5-15% increase in live Christmas tree costs due to inflation this year. This price hike will leave many Americans unable to afford a tree and gifts for their family like they have in years past.


Flanigan, who is known as “The Happiest Man on Earth” to anyone who knows him is the star of a documentary just released in November 2022, which is now streaming on Prime Video and AppleTV. Billy Flanigan: The Happiest Man on Earth, produced by 12th Angel Productions, tells Billy’s incredible story of finding himself and spreading joy to those around him during difficult times by delivering his signature “Flanigrams” and biking miles to deliver them.


Director of the film, Cullen Douglas, recalls working at Disney 25 years ago as a performer and Associate Show Director and stated that even then the name “Billy Flanigan” was legendary, but they never actually crossed paths.


“During the pandemic, I saw all of my Disney cast member friends post about being ‘Flanigrammed’, and I was instantly intrigued,” recalled Douglas. “He later surprised me out here in Los Angeles with my own Flanigram!”


“Billy has traveled over 7000 miles on his bike to deliver Flanigrams and make people smile”, continued Douglas. “Doing a documentary about Billy just made sense because he is the most kind-hearted and authentic person I have ever met.”

About Billy Flanigan

Billy Flanigan: The Happiest Man on Earth is the inspiring journey of Walt Disney World legend Billy Flanigan - from his daunted childhood to a life free of fear, shame, and secrets - all while brightening lives one Flanigram at a time!


  • Billy Flanigan

  • Cullen Douglas, Director of Billy Flanigan: The Happiest Man on Earth

Media Contact

Lisa Wilson -

cell: 352.630.0886

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