BIOGRAPHY of Wynn Stewart
Nashville and Playboy Records
In 1973, his 2nd marriage dissolved and he and his mom moved to Nashville to be with his sister, Beverly. He married again to Doris Massey, who was the daughter of a songwriter friend of his, Cliff Massey, who co-wrote some songs for the "Love's Gonna Happen To Me" album. Like his other marriages, this one didn't last long either. Wynn and his mom lived together in an apartment in Hendersonville, TN, just outside of Nashville. Just next door was Twitty City, where shows by other artists were held regularly under a big tent. Wynn would often visit friends and musicians there.
In 1975 he signed with Playboy Records. His first single under this label was "Lonely Rain", which was released on 6/14/75 and peaked at #80 after 9 weeks on the charts. Then he scored a comeback with a top ten hit, "After the Storm" , released on 7/31/76 and peaked at #8 after spending 14 weeks on the charts. He stayed with Playboy Records for two more years, which resulted in only one other hit single, his own version of "Sing a Sad Song" (released on 11/20/76 and peaking at #19).
In 1978, Wynn started his own independent label, WIN Records, and his first single "Eyes as Big as Dallas", was released on 12/23/78 and peaked at #37. This was followed up by "Could I Talk You Into Loving Me Again", released on 6/9/79 and peaked at #59.
In the early 80's, he decided to step back from performing and took some time away from the spotlight. He did an occasional show to pay the bills but did not attempt any more recording.
During the mid-80's, he decided to launch a comeback with an extensive tour and a new album on his own label, Pretty World Records.