Waylon Jennings may have left the world in 2002, but his musical legacy continues to reveal new chapters. On Diamonds, the second installment in a series of archival releases curated by his son, Shooter Jennings, previously unheard recordings show another glimpse into the outlaw country legend’s creative prime, capturing a younger, more restless Waylon navigating the highs, heartbreaks and complications of love.

Following last year’s acclaimed Songbird, Diamonds takes a decidedly more energetic turn. Its songs share a common thread of romantic turbulence and unrequited affection, with the set anchored by the recently released title track, a remarkable discovery featuring the late Glen Campbell on guitar alongside Jennings and his longtime backing band, the Waylors.

Shooter stumbled across the recording while combing through three separate studio sessions, eventually realizing that Campbell had dropped by during a late December night in 1978. “It quickly became one of my favorite recordings that my dad ever made,” Shooter says. The track also features Gordon Payne, Jerry Bridges, Carter Robertson, Barney Robertson and Rance Wasson. Another highlight is “Saturday Night Special,” an unfinished Lee Clayton song that Shooter helped complete after being struck by the strength of the original performance. The revived recording brings together the Waylors and harmonica great Mickey Raphael, whose playing alongside Jennings and Willie Nelson helped make him a fixture of the outlaw country scene. 

The album also features “Same Old Blues,” a J.J. Cale composition recorded during sessions produced by Tony Joe White for Jessi Colter. The song brings together Waylon’s unmistakable guitar work, White’s playing and the distinctive drumming of Richie Albright, with Colter adding another personal connection to the family musical legacy.

Shooter first opened his father's personal recording archives in 2024, discovering what he describes as a treasure trove of unheard material. The experience inspired him to organize the recordings into distinct collections, beginning with Songbird, an emotional portrait of his father in his prime. Diamonds emerged as its more spirited companion, with two Colter performances helping shape the album’s story.

“The way I wanted to reveal all of this music to the world was part of my job,” Shooter explains. “With Songbird I knew it would be an emotional journey. With Diamonds, it was a higher-energy album, a ‘younger man’s’ album.”

For Shooter, the project is about more than opening the vault. It is an opportunity to reconnect generations of listeners with a man whose voice and songwriting remain very much alive. With help from surviving members of the Waylors and Raphael, he’s brought these long-hidden performances into focus, preserving the spirit of the original sessions while giving the recordings a new life.