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Two things to keep in mind when looking back in time and analyzing why an artist may not have been commercially successful despite having obvious talent.
1) What were they competing with in the marketplace at the time? The late 1980’s was ground zero for the new traditionalist movement in country music and record labels loaded up their rosters with fresh new acts. There was a ton of new material for radio to choose from and it was difficult for new artists to get recognized among all of the tonnage.
2) What was the priority for that new artist from their own record label? When a label has numerous new acts all cannot receive the same promotion push. Music that gets an early positive reception at radio receives the promotional $$$ first.
In Shelby’s case she never broke through due to both factors. Your comment that her style was a bit out of sync with country music trends of that day is on point.
Her style was out of sync with the times and I believe that the fact she was a Billy Sherrill protege may have also hurt her. 1990 was about the time Sherrill was having major problems with the Sony brass and he retired somewhere in that time frame. It was also about the time that George Jones left Epic after 20 years on its roster — part of the reason was supposedly that the label wasn’t promoting his records because of the ongoing dispute with Sherrill. And of course it didn’t help that Shelby developed a reputation for being difficult to work with.
Shelby Lynne does not really seem here like she was being marketed for mainstream/country radio. The emphasis is somewhat limiting. I don’t think anyone since Mickey Gilley made it with more with remakes than new material. And Gilley and Milsap and Van Shelton and others who did remakes didn’t really do them in a retro style.
And then there’s the whole look. In the video, she looks like she’s there for a practice session with the band, rather than a performance, what with the unisex clothing and all. The mainstream women artists of the day–Reba, Trisha, Lorrie, Pam, even Mary Chapin and Mattea–all had a more made up, polished look.
You are completely incorrect. Shelby Lynn was signed by Epic in Nashville and was promoted exclusively as a country act. The offbeat imaging set her apart from the other female acts of that era and actually reflected exactly who she was rather than being a contrived marketing ploy. Shelby is blessed with an amazing voice but the stars did not line up for her at that time to bring about any hits.
As for remakes only ONE of her chart singles was a remake. The remainder were all ORIGINAL songs so your comparison with the other artists is misplaced.