At 14, her traditional country roots led her to Nashville. She and brother Roger Ramey met with Porter Wagoner to show him her songs; Wagoner, though positive, told her to finish high school. At 16, she had a writing/singing stint with the Grand Ole Opry’s Wilburn Brothers, which meant that she could hang around backstage at country music’s shrine, learning from such greats as Wagoner and Dolly Parton.
She cut her first album in 1987. Her first Top 10 hit was ‘If My Heart Had Windows,’ originally a hit for George Jones in 1967. Other hits followed, including ‘A Little Bit in Love,’ ‘Timber, I’m Falling in Love’ and ‘Chains.’
She arrived at Epic Records in 1992. She immediately hit No. 1 with ‘Blame It on Your Heart’ in 1993, from the album Only What I Feel. The heartbreaking ‘How Can I Help You Say Goodbye’ entered the Top 10 in 1994. With the feisty ‘I Try to Think About Elvis,’ and the delicate ‘Here I Am’ and ‘You Don’t Even Know Who I Am,’ When Fallen Angels Fly was awarded the 1995 CMA album of the year — only the second time a woman has won.
With that momentum, Loveless scored two No. 1 hits — ‘You Can Feel Bad’ and ‘Lonely Too Long’ — from 1996’s The Trouble With the Truth. That year, she was voted the CMA female vocalist of the year and the Academy of Country Music’s top female vocalist in 1996. A hard-core country duet with George Jones, ‘You Don’t Seem to Miss Me,’ earned a 1998 CMA vocal collaboration award.
Loveless’ frequent duets with Vince Gill have also earned her accolades. ‘My Kind of Woman, My Kind of Man’ won the 1999 CMA vocal event of the year award and received a Grammy nomination.
Even without hit singles, Loveless was nominated for the CMA female vocalist in 2003, along with fellow traditionalists Dolly Parton, Alison Krauss and Terri Clark. She released On Your Way Home in 2003.