Highwayman - The Highwaymen | Album Review & Ranking: Episode 238 cover art

Highwayman - The Highwaymen | Album Review & Ranking: Episode 238

Highwayman - The Highwaymen | Album Review & Ranking: Episode 238

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Happy Gopher Day! Join James and Connor (aka the Country Road Kid) as we rank and review Highwayman, the debut studio album by country supergroup The Highwaymen! In an attempt to stay relevant in an ever-changing country music landscape, four legends came together to create something different: Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson. After collaborating and admiring each other's work for decades, the Mount Rushmore of rugged outlaw country took to the studio, armed with ten hits like Against The Wind, Deportee, and Cash's own Big River. Would this Hail Mary effort jumpstart their iconic careers?


We'll talk about the four episodes that led us here -- one about each individual Highwayman-- and learn about the holiday specials and films that brought them all together in the first place. We'll explore their group dynamics and talk about the ways music had changed around them between their debuts and 1985. All the while we'll reminisce about panning for gold in the sandbox, hearing these songs as kids, and more. The Mixtaper has facts (or spins) about hotel horses, midwife pranks, and a suspiciously Bill-Murray-adjacent Midnight Breakfast fact. Turn those suits inside out and get ready to ride with some of the genre's greatest.


What do you think about the Highwaymen supergroup? Is this album over- or under-ambitious, and is it the best of their three records to cover in an episode? How do you think the Groundhog Day time loop mechanics work? Let us know in the comments or on socials, and be sure to follow for our Grammy Special coverage next week!


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Thanks for listening!


0:00 Intro

2:05 Relevant Past Episodes

5:20 About The Highwaymen

9:10 About Highwayman

17:48 Awards & Accolades

18:41 Fact Or Spin

21:39 Waylon And Willie Rode Horses In A Hotel

24:36 Waylon And Cash Used Dynamite As Entertainment

26:58 Willie Tricked Kris Into Thinking He Was Delivering A Baby

30:52 Waylon and Cash Loved To Make Midnight Breakfast

37:17 Album Art

38:02 Highwayman

41:19 The Last Cowboy Song

42:23 Jim, I Wore A Tie Today

44:36 Big River

46:55 Committed To Parkview

48:08 Desperados Waiting For A Train

49:20 Deportee (Plane Wreck At Los Gatos)

51:30 Welfare Line

52:20 Against The Wind

54:55 The Twentieth Century Is Almost Over

56:58 Final Spin

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