Cover illustration made with an AI image tool, chosen and framed by the editor.
A playlist for…
Willie and Waylon
The two outlaws, apart and together: Waylon’s and Willie’s own hits, their duets, and the Highwaymen. Roughly in release order, 1968 to 1985, about an hour and twenty minutes.
- Length
- 1h 19m
- Tracks
- 25
- Energy
- Moderate
- Vocals
- With vocals
Songs with singing.
Listen on SpotifyPublished October 29, 2026
Waylon Jennings and Willie Nelson were at the center of country music’s outlaw movement, and this playlist follows them side by side: each man’s own records, the songs they cut together, and the supergroup they formed with Johnny Cash and Kris Kristofferson.
Waylon was born near Littlefield, Texas, in 1937. Buddy Holly hired him to play bass, and Waylon gave up his seat on the 1959 flight that killed Holly. Willie was born in Abbott, Texas, in 1933, and first made his name writing songs that became hits for others, most famously Patsy Cline’s “Crazy.”
The playlist runs roughly in release order. It starts with Waylon’s 1968 “Only Daddy That’ll Walk the Line” and Willie’s 1973 Shotgun Willie, then moves through the mid-1970s albums that made them stars. Wanted! The Outlaws (1976), with Jessi Colter and Tompall Glaser, became the first country album certified platinum. The duets follow: “Good Hearted Woman,” “Luckenbach, Texas” and “Mammas Don’t Let Your Babies Grow Up to Be Cowboys.” Then come the solo hits of the late ’70s and early ’80s, two duets Willie made with other legends, and the Highwaymen.
Waylon died in 2002, a few months after he was inducted into the Country Music Hall of Fame. Put this on for a long drive.
Tracklist
Side A
- 01Only Daddy That'll Walk the LineWaylon Jennings2:20
Released July 13, 1968, and a No. 2 country hit for Waylon. [source]
- 02Shotgun WillieWillie Nelson2:37
- 03Whiskey RiverWillie Nelson4:07
- 04Lonesome, On'ry and MeanWaylon Jennings3:41
- 05Bloody Mary MorningWillie Nelson2:49
- 06This TimeWaylon Jennings2:27
- 07I'm a Ramblin' ManWaylon Jennings2:50
- 08Blue Eyes Crying in the RainWillie Nelson2:21
From Red Headed Stranger (1975), and Willie’s first No. 1 hit as a singer. [source]
- 09Are You Sure Hank Done It This WayWaylon Jennings2:59
A No. 1 hit from Waylon’s 1975 album Dreaming My Dreams. [source]
- 10Dreaming My Dreams with YouWaylon Jennings2:26
- 11Good Hearted WomanWaylon Jennings & Willie Nelson · Wanted! The Outlaws3:01
From Wanted! The Outlaws (1976), with Waylon, Willie, Jessi Colter and Tompall Glaser: the first country album certified platinum. The duet shared Single of the Year at the 1976 CMA Awards. Spotify lists this recording as made at Western Place in Dallas in September 1974. [source 1] [source 2] [source 3]
- 12Luckenbach, Texas (Back to the Basics of Love)Waylon Jennings & Willie Nelson3:22
- 13Mammas Don't Let Your Babies Grow Up to Be CowboysWaylon Jennings & Willie Nelson2:38
From the 1978 album Waylon and Willie. It won the 1979 Grammy for Best Country Performance by a Duo or Group with Vocal. [source]
Side B
- 14I Can Get Off on YouWaylon Jennings & Willie Nelson · Remastered2:28
- 15Georgia on My MindWillie Nelson4:23
From Stardust (1978), an album of old standards that observers predicted would ruin Willie’s career. It went platinum the same year. [source]
- 16I've Always Been CrazyWaylon Jennings4:17
- 17AmandaWaylon Jennings2:59
Waylon first cut it for The Ramblin’ Man in 1974. In 1979 new overdubs were added to that recording for his first greatest-hits album, and the single spent three weeks at No. 1. This is that 1979 version. [source]
- 18Theme from The Dukes of Hazzard (Good Ol' Boys)Waylon Jennings2:10
Waylon narrated The Dukes of Hazzard as its Balladeer starting in 1979, and sang this theme. [source]
- 19On the Road AgainWillie Nelson · Honeysuckle Rose soundtrack2:37
From the Honeysuckle Rose soundtrack. It reached No. 1 on Billboard’s Hot Country Songs chart in 1980. [source]
- 20Always on My MindWillie Nelson3:33
It topped Billboard’s Hot Country Singles, and the release won three awards at the 25th Annual Grammy Awards. [source]
- 21Just to Satisfy YouWaylon Jennings & Willie Nelson2:50
- 22Pancho and LeftyMerle Haggard & Willie Nelson4:47
- 23Seven Spanish AngelsWillie Nelson & Ray Charles3:51
- 24HighwaymanThe Highwaymen3:04
The title track of the Highwaymen’s 1985 album: Waylon, Willie, Johnny Cash and Kris Kristofferson. Willie became the group’s last surviving member after Kristofferson died in September 2024. [source 1] [source 2] [source 3]
- 25Desperados Waiting for a TrainThe Highwaymen4:38
Total1h 19m
At a glance
- How long is the “Willie and Waylon” playlist?
- 1 hour 19 minutes, 25 tracks, played in the order listed.
- Does it have singing?
- Songs with singing.
- Where can I listen to it?
- On Spotify, as a public playlist. Anyone can see the tracklist there, and playing it needs the Spotify app or web player.
- Who made it?
- It was picked, put in order and listened through by the editor at A Playlist For…. Software did not choose the songs.