Hilton Head Sea Pines’ singer inspires documentary on Apple TV. Here’s a peek

Gregg Russell has strummed his guitar to hundreds of fans in Hilton Head’s Sea Pines for more than 40 summers. Last month, his audience became bigger with a new Apple TV documentary.

“Gregg Russell: ‘If This Old Tree Could Talk’” tells how Russell came to perform in Harbour Town. It follows Russell from his early performances at Walt Disney World to sleeping in a Chevy van in Coligny Plaza to becoming an island institution. The 1 hr 21 minutes documentary premiered on Apple TV on June 24.

“I’m not getting any younger,” Russell said of why he agreed to the documentary, produced by Fisher Films and brothers Daniel and Stephen Fisher. The brothers were “like a dog with a bone,” when it came to asking Russell to participate, he said.

And while the brothers started producing the self-funded film one year ago, their relationship with Russell goes back over 30 years. Then, a five-year-old Daniel climbed the steps underneath Liberty Oak in Harbour Town to Russell’s stage. To this day, children vie for a chance to sing on stage with cardboard posters. That day, little Daniel won Russell’s attention and sang “This Little Light of Mine” on stage.

“That’s a classic,” Russell said, laughing. There are also classics that only those who have sat with Russell on a warm Lowcountry night would recognize: the songs he wrote himself. Most summer nights at Sea Pines, children sit singing about purple people eaters and unicorns for an hour and a half and taking the Bubble Gum Pledge to “drive (their) parents crazy.”

What those tourists and residents may not recognize is Russell’s philanthropic work, which the documentary details.

“My wife and I have flown under the radar with what we’ve done in our personal lives over the last more than 20 years,” Russell said. They founded the Hilton Head Heroes Program, which allowed families with terminally ill children to have vacations in Sea Pines and on Hilton Head Island.

“If I have a legacy, and I’m not saying I do, I think that’s probably it,” Russell said.

Russell said being silly is great, but he hopes he is remembered for the children and families that the Heroes Program helped. “We always tried to do it in a way that was protective and private to these families,” he said. Russell explained that the documentary explains his philanthropy tactfully and in an uplifting way.

That’s another reason this documentary sets itself apart from others, Stephen said: it’s not “heavy stuff” such as the true crime that frequents most-watched lists. The documentary was trending at #1 for documentaries on Apple TV when it was released, according to Stephen.

“This is a feel-good story and it’s about family,” Stephen said. “There’s not many stories like this being told these days.”