When Waylon Jennings passed in 2002 at age 64, he left behind more than 16 No. 1 hits and the blueprint for outlaw country — he left a family of seven children across four marriages, each carrying pieces of the gravel-voiced rebel’s spirit. From Shooter Jennings’ chart-topping outlaw anthems to Terry Vance’s behind-the-scenes hustle and Struggle Jennings’ rap-infused country, the Jennings clan has transformed personal loss into a multi-generational dynasty. As detailed in Wide Open Country’s intimate portrait, these heirs aren’t just preserving Dad’s legacy — they’re expanding it, one note, one story, one tribute at a time.

The family tree spans heartbreak and harmony. Jennings’ first marriage to Maxine Caroll Lawrence (1955–1962) produced four children: Terry Vance (1957–2019), Buddy Dean, Julie Rae (died 2014), and Deana (died 2015). His brief union with Lynne Jones (1962–1967) brought adopted daughter Tomi Lynne. Third wife Barbara Rood had no children with him. But it was fourth wife Jessi Colter — married in 1969 — who gave him lasting love and two musical heirs: son Shooter (born Waylon Albright, 1979) and stepdaughter Jennifer “Jenni” Eddy Jennings (from Colter’s prior marriage to Duane Eddy).

Shooter Jennings: The Direct Heir Carrying the Outlaw Torch The youngest biological son, Shooter grew up on tour buses, absorbing his parents’ rebel ethos. Named after Waylon’s nickname for friends (“Shoot ’em straight”), he debuted with 2005’s Put the O Back in Country — a defiant return to roots that hit No. 22 on Billboard Country. Nine studio albums later, including 2018’s self-titled Shooter and 2024’s Sometimes Y, he’s produced icons like Tanya Tucker (her Grammy-winning While I’m Livin’) and Brandi Carlile. Shooter played his dad in Walk the Line (2005) and married Misty Brooke Swain in 2013; they share two kids. “Dad taught me music’s about truth, not trends,” he told Rolling Stone in 2025. His latest project: a Highwaymen tribute tour with Kris Kristofferson Jr.

Terry Vance Jennings: The Road Warrior Who Wrote the Book Eldest son Terry was Waylon’s shadow — selling merch at 12, managing production by 20. He scouted talent for labels and founded Korban Music Group before his 2019 death at 62 from heart complications. His 2016 memoir Waylon: Tales of My Outlaw Dad — a New York Times bestseller — revealed tender moments, like Waylon teaching him guitar on a Phoenix porch. “He wasn’t just a star,” Terry wrote. “He was my hero who cried when I graduated.” Posthumously, Korban released unreleased Waylon demos in 2023, raising $500K for diabetes research.

Buddy Dean Jennings: The Namesake Honoring a Tragic Legacy Named for Buddy Holly — whose 1959 plane crash Jennings survived by giving up his seat — Buddy Dean has stayed low-key but loyal. A regular at Shooter’s shows and annual Luckenbach tributes, he manages the family’s Littlefield ranch. “Dad never got over that night,” Buddy shared in a 2024 podcast. “Naming me kept Holly alive.” He oversees the Waylon Jennings Museum, opened 2025 in Lubbock.

The Daughters: Quiet Strength Amid Loss Julie Rae, Deana, and Tomi Lynne lived privately. Julie battled cancer bravely before passing in 2014; Deana followed in 2015. Tomi Lynne, adopted during Waylon’s Phoenix days, runs a horse rescue in Arizona — “Dad loved animals more than fame,” she says. Their stories surface in family reunions, like the 2023 Jennings Jamboree in Luckenbach, where Shooter performed “Good Hearted Woman” with Tomi’s grandkids.

Jenni Eddy Jennings & Struggle Jennings: The Extended Outlaw Line Jenni, raised as Waylon’s own, gifted the world grandson William “Struggle” Harness — a rapper-turned-country artist blending trap beats with honky-tonk soul. His 2018 debut Waylon & Willie went viral; 2024’s Troubadour of Troubled Souls features Shooter. The four-generation collab “Ace in the Hole” (2019) with Jenni, Jessi, Struggle, and great-granddaughter Brianna Harness hit 10 million streams. “Granddad’s blood runs deep,” Struggle told Billboard. Jenni manages the family’s publishing catalog, ensuring every royalty honors Waylon’s fight for creative control.

The Jennings legacy thrives in 2025: Shooter’s producing Sturgill Simpson’s next album; Struggle headlines Red Rocks; the family launched the Waylon Jennings Outlaw Fund, granting $1M to young Texas songwriters. At the 2024 CMA Awards, a tribute medley — Shooter, Struggle, and Lainey Wilson — brought the house down with “Mammas Don’t Let Your Babies…” As Jessi Colter, 78, said at the event: “Waylon’s kids didn’t just inherit songs — they inherited the fight to sing them their way.”

From merch tables to million-stream anthems, Waylon’s children prove the outlaw spirit isn’t dead — it’s family.