(This happened.)
Texas Monthly/ The NY Times has an oral history up of the 1996 collaboration between Waylon Jennings and the Old 97's:
In 1996, five Texans met in Nashville to record two songs together. At the time, the four members of the Dallas band Old 97’s were awaiting the release of their major-label debut for Elektra Records, “Too Far To Care.” But already they were considered too loud for country, too country for rock. It was a struggle that the fifth Texan in the room, Waylon Jennings, knew all too well.
The fruits of that meeting, versions of "The Other Shoe"* and "The Iron Road", are being released today by Ominvore Recordings, along with four Old 97's demos. Get to a record store!
Previous posts on the Old 97's here and here.
*"The Other Shoe" is my all-time favorite Old 97's song. Except maybe for "Salome". Or "Big Brown Eyes". Anyway, Waylon had good taste.
