He signed with Asylum Records and in 1998 turned in Cold Coffee Morning as his third album. The record company folded just as the record was about to be issued. He recorded Willin' for independent Eminent Records, which was released with much critical acclaim in 1999, but that label later went out of business as well.
Jon Randall contented himself with recording-session work as a singer and guitarist and by joining one of his musical heroes on the road. As a member of Sam Bush's band, he recorded Glamour & Grits (1996) and Howlin' at the Moon (1998). He and Bush then toured and recorded with Lyle Lovett's group.
But many in Nashville still believed he should be concentrating on his own music. Patty Loveless hired him as her duet partner on Mountain Soul (2001) and Bluegrass & White Snow (2002). The two were also teamed to duet on the album Livin,' Lovin,' Losin,' which became his second Grammy-winning CD.
"How can I get you off the road to stay home and write songs?" asked music publisher Ree Guyer-Buchanan two years ago. Recalls Randall, "I promised her I'd stay home and write songs for her company, Wrensong. It was hard for me to make that transition. I did tour with Earl Scruggs last year. How could I turn that down? But otherwise, I kept my word."
Last year his songwriting gate swung wide, with more than a dozen artists recording his tunes. "Whiskey Lullaby," cowritten with Bill Anderson, was sung to fame by Brad Paisley and Alison Krauss.
"Next door to Wrensong on Music Row was DMZ Records and [its then executive] John Grady. It turned out, he was a big fan of my first record. He was actually aware of who I was and what I was doing, which was pretty cool. Since his office was next door, he'd come over, hang out, drink coffee and talk about music. After he moved over to Sony, he came to me about doing a record.
"As soon as we started talking, I said, 'Whatever we do, whatever this turns out to be, I want to work with George Massenburg. I first met George on the Seldom Scene session. That's why I insisted on working with him. I had never worked with him, but I'd loved everything he'd ever done - Little Feat, The Trio (Linda Ronstadt, Dolly Parton, Emmylou Harris) and on and on."
Fate stepped in when Randall was hired to play guitar on a Seldom Scene album, produced by Massenburg. The two men bonded instantly. And that convinced the singer-songwriter that he did, indeed, want to make another album.
"George is a genius. He's brilliant about microphone placement and so many other things. A lot of these songs were recorded live in the studio, sitting in a room together with no headphones and just playing. When I tell people that, I know the first thing they think is, 'Oh this is one of those arty, too-cool records.' The truth of the matter is, the reason we recorded it that way is because it sounds bigger. The production sounds enormous because of all the natural reverb in the room and the way George captures sounds.
"It was a priceless experience. Spiritually and emotionally I've matured a lot. So once we started recording this music, I really knew what I wanted it to be and where I wanted it to go.
"I stayed home. I did my job as a writer. And now I've found a group of people who believe in me as an artist. I can't tell you what a great feeling that is."