The Highwaymen Announce Live Box Set, Premiere Documentary Trailer

Nearly 30 years after Elvis Presley, Jerry Lee Lewis, Carl Perkins and Johnny Cash all swapped gospel harmonies during the “Million Dollar Quartet” jam at Sun Studio in 1956, a different sort of supergroup — the Highwaymen — released their first album. Cash was part of that lineup too, teaming up with his old roommate Waylon Jennings and Texas titans Kris Kristofferson and Willie Nelson. The result was something rarely seen during the early days of country music’s climb into the mainstream: a group of elder statesmen who could still top the charts, speeding past the younger acts of the genre.

The Highwaymen’s trip started in 1985 and wrapped up one decade later. The group released three albums along the way, but their video output was a bit more spotty, with a bizarre, made-for-TV version of John Wayne’s Stagecoach — featuring all four bandmates in major roles, including Nelson as a somewhat stoned Doc Holliday — bringing them together for the longest time onscreen. That changes this May, when PBS premieres a new installment of its American Masters documentary series, The Highwaymen: Friends Till the End, and Legacy teams up with Columbia Records to release a four-disc CD/DVD package, The Highwaymen Live – American Outlaws. The live box set hits stores May 20th, while the documentary premieres a week later on May 27th.

Both the American Masters program and the Columbia/Legacy DVD (also available on Blu-Ray) include rare footage from a Highwaymen show in March 1990, while the guys were touring though Uniondale, New York, in support of their second album. The performance shows all four frontmen sharing the spotlight, lined up against the lip of the stage with guitars across their chests and smiles splashed across their faces. Backed by equally legendary sidemen like pedal-steel guitarist Robby Turner (who currently tours with Chris Stapleton), guitarist Reggie Young (whose playing can be heard on Dusty Springfield’s “Son of a Preacher Man” and J.J. Cale’s “Cocaine”) and harmonica wiz Mickey Raphael, the group performed 35 songs that night, filling the better part of three hours with a mix of Highwaymen songs and hits from their solo catalogs.

The PBS show also includes new interviews from the band’s surviving members and archival footage from both Cash and Jennings, who died within two years of each other in the early 2000s. Meanwhile, The Highwaymen Live‘s three CDs round up live performances from a pair of Farm Aid festival performances in 1992 and 1993, a complete recording of the Uniondale show and a new version of Bob Dylan’s “One Too Many Mornings,” originally released by Cash and Jennings on the pair’s 1986 duets album, Heroes. This time around, Nelson and Kristofferson share lead vocals on an updated recording of the song, paying tribute to their late bandmates.

“I had three of my favorite people out there, [so] it was some of the best times of my life,” Nelson says in the documentary’s trailer, which makes its premiere today on Rolling Stone Country.

Here’s the complete tracklist for The Highwaymen Live – American Outlaws.

Disc 1 (Recorded live at Nassau Coliseum in Uniondale, New York, March 14, 1990)
1. Mystery Train
2. Highwayman
3. Mammas Don’t Let Your Babies Grow Up to Be Cowboys
4. Good Hearted Woman
5. Trouble Man
6. Amanda
7. There Ain’t No Good Chain Gang
8. Ring of Fire
9. Folsom Prison Blues
10. Blue Eyes Crying in the Rain
11. Sunday Morning Coming Down
12. Help Me Make It Through the Night
13. The Best of All Possible Worlds
14. Loving Her Was Easier (Than Anything I’ll Ever Do Again)
15. City of New Orleans
16. Always on My Mind
17. Me and Bobby McGee

Disc 2 (Recorded live at Nassau Coliseum in Uniondale, New York, March 14, 1990)
1. Silver Stallion
2. The Last Cowboy Song
3. Two Stories Wide
4. Living Legend
5. The Pilgrim: Chapter 33
6. They Killed Him
7. I Still Miss Someone
8. Ragged Old Flag
9. (Ghost) Riders in the Sky
10. Are You Sure Hank Done It This Way
11. Night Life
12. The King Is Gone (So Are You)
13. Desperados Waiting for a Train
14. Big River
15. A Boy Named Sue
16. Why Me
17. Luckenbach, Texas
18. On The Road Again

Disc 3 (Live tracks recorded at Farm Aid V and Farm Aid VI, March 1992 and April 1993)
1. Mystery Train
2. Highwayman
3. The King Is Gone (So Are You)
4. I’ve Always Been Crazy
5. The Best Of All Possible Worlds
6. City of New Orleans
7. Folsom Prison Blues
8. Intro/Highwayman
9. Shipwrecked in the Eighties
10. Desperados Waiting for a Train
11. One Too Many Mornings (Previously Unreleased Studio Recording)