Waylon Jennings and Robert Duvall went way back… and with the actor’s recent passing, now’s a good time to revisit the Hollywood-Outlaw connection the two had. This past Sunday, the Academy Award-winning actor passed away at the age of 95. Duvall was known for the countless films and television shows he starred in during his career that got started in 1960. Some might know him from classic movies like The Godfather, Days of Thunder, Apocalypse Now, and the country music film Tender Mercies. Others might remember him for his more comedic roles in Kicking and Screaming and Four Christmases. He’s a name that will go down in the history books as one of the best actors of all time, and his wife, Luciana, shared this message earlier today letting the world know that Robert Duvall had passed on: “Yesterday we said goodbye to my beloved husband, cherished friend, and one of the greatest actors of our time. Bob passed away peacefully at home, surrounded by love and comfort. To the world, he was an Academy Award-winning actor, a director, a storyteller. To me, he was simply everything. His passion for his craft was matched only by his deep love for characters, a great meal, and holding court. For each of his many roles, Bob gave everything to his characters and to the truth of the human spirit they represented. In doing so, he leaves something lasting and unforgettable to us all. Thank you for the years of support you showed Bob and for giving us this time and privacy to celebrate the memories he leaves behind.” If you were to scroll through all of his acting credits, you’d likely be overwhelmed. I’ve already mentioned a number of projects Duvall starred in… but that was just scratching the surface. For over six decades, Robert Duvall brought his prowess to movies and TV shows far and wide. He even starred in a little something for Waylon Jennings. One of the credits on Duvall’s IMDB is for a Waylon’s “America” music video. That’s a little bit misleading, because Duvall doesn’t appear in that music video… but does appear in a production with a 37-minute run time called Waylon Jennings America. The long-form music video features songs from Jennings’ catalogue like “The Conversation,” “Never Could Toe The Mark,” and “America.” Smack dab in the middle of it, Robert Duvall plays a doctor of psychiatry in a clip where viewers get to see the Hollywood legend help Waylon through a therapy session. Duvall asks questions like “Why do you write about women in your songs?” and “What was it like growing up in West Texas?” and even “What time of day do you write the best songs?” From what I can tell, Waylon provides realistic answers… even though it all seems to be more of a joke than anything else. There’s even another country music cameo at the very end that you’ll want to stick around for (excuse the grainy footage): Pretty cool to see Robert Duvall, Waylon Jennings and Johnny Cash all together… and to hear Waylon tell a story about Shooter. Evidently, Duvall got along quite well with Waylon, and the two were good friends. And speaking of Shooter, the son of Waylon shared a message of his own when he found out about the passing of the Hollywood legend. Shooter Jennings says that his father and Duvall were close, and the actor’s connection to the Jennings family even included some help with Robert Duvall’s role in The Apostle: “Oh man! Robert Duvall and my dad were friends. We stayed at his house one time when I was a teenager. He had pot bellied pigs running around. He was so nice. He studied my mom’s mother and her family for the role in ‘The Apostle.’ My dad loved ‘Tender Mercies’ (as do I), but my dad really felt that he had nailed the West Texas accent in that movie and had really captured the spirit of a character like that. So sad to hear he’s passed away. He was one of my favorites. From ‘To Kill A Mockingbird,’ to ‘Network,’ to ‘Falling Down,’ I love all of his movies. Rest in Peace, Bobby!” Oh man! Robert Duvall and my dad were friends. We stayed at his house one time when I was a teenager. He had pot bellied pigs running around. He was so nice. He studied my mom’s mother and her family for the roll in the Apostle. My dad loved Tender Mercies (as do I), but my… — Shooter Jennings (@shooterjennings) February 16, 2026 Here’s a picture of the two together in Malibu back in the 80s… Photographer Alan Messer says: “I took this photograph of Steve singing “City Of New Orleans” with Waylon and Robert Duvall at Duvall’s Serra Retreat home in Malibu, California, in the summer of 1984. Also in this picture are Gail Youngs (Duvall’s then wife), Jessi Colter, and Charlie Feldman. Party guests included film production people, directors, actresses and actors such as Sean Penn. Steve Goodman was in great form, singing brilliantly, meanwhile knowing he was very ill.” RIP Robert Duvall.The post The Late, Great Robert Duvall Was Friends With Waylon Jennings & Once Starred In A Music Video Production With The Country Star first appeared on Whiskey Riff.