In 2008, Patty Loveless was driving home to Georgia with one of her own recordings playing. It was “How Can I Help You Say Goodbye,” the 1994 hit about a daughter who loses one thing after another and is comforted each time by her mother, until the last verse puts her at her mother’s bedside. The version she had on was an old live recording, made years earlier. Listening to her own voice sing that verse, she found herself with tears in her eyes.
She described the feeling as emotions rushing at her like rapids. Then she explained why the song hit differently now.
“Now I’ve lived through that song.”
She said she connected to every part of it, after what she had been through with her own mother.
The Week She Stayed
Patty Loveless lost her mother, Naomi Ramey, in 2006. Her mother had fallen ill the year before, and Patty was there for the last week of her life. Naomi did not die alone. Her children, grandchildren and great-grandchildren were around her at the end.
Patty later spoke about trying to help everyone in the family through it, noting that women so often end up as the caregivers. Her brothers were struggling. She and her two sisters held together. It came on top of other losses: her mother-in-law died in 2005, and that same year her brother Roger, who had helped launch her career, suffered a stroke and the family spent a year unsure he would survive.
By the end of it, she said, she felt burned out. She had stepped away from touring in late 2005 and stayed away for three years. She told one interviewer in 2008 that she had needed to go through a process of healing, and that music had been like a good friend through it.
A Song That Was Already Hard to Sing
“How Can I Help You Say Goodbye” had never been an easy song for Patty Loveless. It was written by Karen Taylor-Good and Burton Collins, an actor who had never written a song before. The title came from his grandmother, who spoke those words to him shortly before she died in 1988. Collins said he and Taylor-Good finished the song in about three hours.
When Patty recorded it for her album Only What I Feel, it got to her. In 1993 she said she cried every time she tried to record it, and that a letter from Collins gave her the strength to finish. The trade magazine Gavin Report noted at the time that she had a hard time getting through it in the studio.
Released as a single in March 1994, the song climbed to No. 3 on Billboard’s country chart that June and earned Grammy nominations for Best Female Country Vocal Performance and Best Country Song. But when Patty first cried over it, the last verse was still something she was imagining. By 2008, it was something she remembered.
Warning the Band
Patty Loveless was getting ready to go back on the road that fall. She had a new album of classic country songs, Sleepless Nights, and her first tour in three years was on the calendar. Rehearsals were set to start the following week.
She said it had been years since the band had played “How Can I Help You Say Goodbye” on tour, and she was not sure she could get through it. She had already told the musicians it was going to be hard.
It had happened to her on stage before. In the same conversation, she remembered a show in Ohio in 1996, when her older sister Dottie had just had surgery. Partway through a verse, Patty started crying on stage. Dottie died later that year.
What She Wanted the Song to Do
For all of that, Patty Loveless did not talk about the song as something to avoid. She said she wanted to deliver it as a song that heals, and to give people hope even through the sadness in it. Music, she said, was her own way of healing.
In 1993, she had cried in the studio over a goodbye she had not lived yet. In 2008, getting ready to sing it again, she had already sat through that last week herself.