Waylon Jennings may have left this world more than two decades ago, but his voice and legacy are still riding high thanks to his son, Shooter Jennings, who just confirmed that a new Waylon documentary is officially in the works. In true outlaw fashion, it is shaping up to be one that fans will not want to miss.
Shooter broke the news after responding to a fan on social media who asked why there were so many documentaries about artists that did not matter and not one about Waylon. Shooter fired back with an update that stopped country fans in their tracks. He confirmed that a documentary on his father is already being made, directed by his longtime friend Greg Olliver, who worked on Lemmy and Chasing Whiskey. He also revealed that Willie Nelson has already been interviewed for the project.
“There is an official Waylon documentary underway with my good friend Greg Olliver directing,” Shooter shared. “Willie was interviewed yesterday. He also filmed all of me finding, preparing and finishing the ‘Songbird’ and future albums.”
That mention of Songbird ties right into the project that has already had fans talking all year. Released in 2025, Songbird is the first of three posthumous Waylon albums that Shooter has been working on, all built from lost recordings tracked between 1973 and 1984. Shooter discovered the tapes while digging through old archives, and the music was already close to finished. He added some modern touches and harmonies, but mostly let his dad’s raw sound do the talking.
“This project has given me an entirely new chapter in my relationship with my father,” Shooter said earlier this year. “Working on this music has brought a whole new understanding about how, when and why my dad made music. The hard work is there on the tapes, and the passion and the soul within is as alive today as it was the day it was recorded.”
While no official release date has been announced, fans are already buzzing about what the film might include. Since Greg Olliver documented Shooter’s process of uncovering and finishing Waylon’s Songbird sessions, it is safe to expect a behind-the-scenes look at both the music and the man. Between rare studio footage, unseen moments from the Jennings family vault, and new interviews with those who knew Waylon best, this film has the potential to be the definitive story of one of country music’s most iconic rebels.
For You
Waylon Jennings lived a life that was larger than any song. He was the heart of the outlaw country movement and a man who carved his own path while changing the course of Nashville in the process. Alongside Willie Nelson, Johnny Cash, and Kris Kristofferson, he helped form the Highwaymen, one of the greatest supergroups the genre has ever known. With Willie sitting down to share his memories for this documentary, it is clear the film will honor more than Waylon’s music. It will celebrate the brotherhood and spirit that defined an era.
Shop Willie Nelson
- Greatest HitsVinylWith “On the Road Again,” “Always on My Mind” and “Crazy”See it on Amazon
- Red Headed StrangerVinylWith “Blue Eyes Crying in the Rain”See it on Amazon
- It’s a Long Story: My LifeBook · 2015His memoir, written with David RitzSee it on Amazon
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Shooter’s hands-on role makes the upcoming project even more personal. It is not just another filmmaker revisiting a legend. It is a son honoring his father by helping the world understand the man behind the myth. With the combination of lost recordings, new reflections, and rare interviews, this film is set to pull back the curtain on the grit, grace, and genius that made Waylon Jennings an enduring force in country music.
More than twenty years after his passing, Waylon’s story is still being told. Thanks to Shooter, the legend keeps getting louder.
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