99 You Win Again Hank Williams 1952 Written by Hank Williams Hank Williams died on January 1, 1953, at the age of 29.
@Cobalt are you including Bob Wills? Also, are you counting team ups like Jimmy Buffet and Alan Jackson? Can we have rock singers who have done country songs or albums like Mike Ness?
Thanks Federal Farmer, for posting your questions. I have included old timers. I have included artists working together. There are 100 songs. Eight are collaborations, so there are 108 artist credits. There are 50 different artists. All are primarily country artists. 25 of the artists are in the Country Music Hall of Fame.
97 I'll be Your San Antone Rose Emmylou Harris 1977 Written by Susanna Clark Emmylou Harris and the Hot Band performing at the BBC Theater for the late night show "The Old Grey Whistle Test".
91 My Baby Loves Me Martina McBride 1993 Written by Gretchen Peters Gretchen Peters was elected to the Nashville Songwriters Hall of Fame in 2014.
84 I'll be Your Baby Tonight Kris Kristofferson Bob Dylan 30th Anniversary Concert, Madison Square Garden, October 16, 1992 Written by Bob Dylan
82 Golden Ring Alan Jackson and Lee Ann Womack For George Jones' 80th Birthday, October 4, 2011. Written by Bobby Braddock