Welcome to the latest episode of The Icons of Outlaw Country, where the spirit of rebellion, heartbreak, and wide-open highways never fades. Today we’re kicking off with the cosmic collision that changed everything: the Byrds taking country into the stratosphere at Sweetheart of the Rodeo in ’68, Gram Parsons’ cosmic cowboy dreams spilling straight into the Flying Burrito Brothers’ Sin City sermons, and Kris Kristofferson staring down the devil himself with nothing but a beat-up guitar and the truth. These were the renegades who tore Nashville’s rulebook in half, slipped on a pair of old Levi’s, and then slipped a switchblade into their cowboy boots, proving that country music could be dangerous, poetic, and stone-cold cool all at once.
Then we ride deeper into the outlaw bloodline with two of the rowdiest, realest partnerships ever put on tape: David Allan Coe and George Jones trading verses like outlaws swapping whiskey shots, and Merle Haggard joining Possum on Yesterday’s Wine for a masterclass in hard-living wisdom. Add Marshall Chapman’s Georgia-fire swagger and Townes Van Zandt’s haunting live Marie, and you’ve got the pure, unfiltered heart of a movement that refused to bow to radio suits or rhinestone expectations. This is outlaw country at its finest: rough around every edge, honest to the bone, and still raising hell fifty years later. Turn it up, pour something strong, and let the icons take the wheel.
Original air date: 11/22/25
PLAYLIST
HOUR ONE:
The Byrds – Life in Prison – 1968
The Byrds – You Ain’t Going Nowhere – 1968
The Flying Burrito Brothers – Sin City – 1969
The Flying Burrito Brothers – Do You Know How It Feels – 1969
David Allan Coe & George Jones – This Bottle (In My Hand) – 1980
Merle Haggard & George Jones – Yesterday’s Wine – 1982
Johnny Paycheck & George Jones – When You’re Ugly Like Us – 1980
Kris Kristofferson – To Beat the Devil – 1970
Sir Douglas Quintet – Mendocino – 1969
Marshall Chapman – Somewhere South of Macon – 1977
The Flatlanders – Dallas – 1976
Joe Ely – Me & Billy the Kid – 1998
Kinky Friedman – Get Your Biscuits in the Oven – 1973
HOUR TWO
Michael Murphey – Cosmic Cowboy/Cosmic Breakdown (Live) – 1978
Billy Joe Shaver – Tramp on Your Street – 1993
Townes Van Zandt – Marie (Live) – 1991
Marshall Chapman – Crystal Clear – 1977
Gary Stewart – Oh, Sweet Temptation – 1976
Ed Bruce – This Old Hat – 1988
Ed Bruce – This Is the Last Cowboy Song – 1980
Creed Fisher – Jesus, Haggard & Jones – 2020
Wade Reeves – Oil Field Trash – 2015
David Allan Coe – Jack Daniels if You Please – 1978
Willie Nelson – The Border – 2024