Yes he did along with Phil Weir and Tony Goble
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In the mid-1980s, Johnny Cash, Kris Kristofferson, Willie Nelson, and Wayland Jennings formed a successful group called The Highwaymen.
"On the Road Again" is a song by the blues group Canned Heat released as a single in August 1968.An electro-rock cover version of the song by the French band Rockets appeared on their 1978 album On the Road Again.For the source and more detailed information concerning this subject, click on the related links section indicated below.
Do you mean the song "Take Me Home Country Roads" ? If you do its by "Apres Ski Hut" . ~ I feel the singer required is more likely to be the singer of "On The Road Again" it was written and performed by Willie Nelson. It could also be "Six Days On The Road" - Sung by Dave Dudley. If by any chance it actually was "Take Me Home Country Roads" I feel the answer probably required is John Denver (who also wrote it) - although it has been sung and recorded by several other artistes)
No, Robert Plant did not sing a song called on the road.
I know a song by Willie Nelson called "Over You Again." Also another song by Toto reminds me of the words "over you." Hope this helps. Delimomma