As soon as the brass ring was within reach, Olson, tired of life on the road, climbed off the carousel in 1995 and retreated to his Joshua Tree, Cal. home/studio.
When Olson re-emerged in 1996, the band that came out with him bore little resemblance to the reconfigured sans-Olson Jayhawks. With wife and folk/pop singer Victoria Williams and bassist Mike "Razz" Russell, Olson unveiled the stripped down lo-fi country elegance of the Original Harmony Ridge Creekdippers and began a musical regimen of self-releasing an album a year.
Olson had acquired and strangely turned his back on everything that an artist pursues - major label status, a stable band line-up, a growing national audience. The Creekdippers were supposed to be the antithesis of all that he had experienced, as well as a practical method of creating music and making it possible to negotiate the limitations of Williams' well-publicized multiple sclerosis.
Olson admits his path has been somewhat circular, although he is still a long way from where he was with The Jayhawks.
"I liked playing with Vic and Mike at the house, and it seemed like something to do where we could actually write some songs, play and record them, learn about that whole thing from having to do it and not have other people involved," Olson says of the 'dippers beginnings. "Just kind of do something for awhile. Once you get companies or managers involved, it gets complex, and I was really into simplifying my life, I guess. And I certainly simplified it."
"I'm starting to see the light. I would like to get out and get some records in stores. I have a little more ambition these days."
That slight rise in ambition inspired one of the more legitimate ventures in the Creekdippers' history, namely getting signed to a major indie label and obtaining a wider release for the band's latest, "My Own Jo Ellen," on HighTone Records.
Olson decided that this would be the big touring year and the best chance to get sales from a tour would be to sign to a label that could stock the stores with their product, an almost impossible hurdle for a singer putting out his own music.
But even this one bid for normalcy has its own Dipperesque aspect. The release of "My Own Jo Ellen" would generally mean that the Creekdippers would be headed out on tour to promote the album.
When the Creekdippers hit the road for a West Coast circuit in December, it will already be the third leg of a touring cycle that began six months before the album was released. First, the band did a series of warm-up dates in Minnesota in the spring followed by a month-long opening slot on Lou Reed's Ecstasy tour, which led to more Creekdippers dates nationwide.
Basically, the upside down tour-album release schedule was a result of having to work the album into HighTone's release pipeline once the band had settled on the label, which delayed the album's official debut.
Originally, "My Own Jo Ellen" was to have been released well before Williams' new solo outing, "Water to Drink," (Atlantic) also recorded at the couple's home studio just prior to the recording of the Creekdippers' album.
A lot of the same people show up on both albums, (including drummer Don Heffington and engineer Michael Dumas), but the sessions were completely separate.
"Vic went in to mix her album in Los Angeles, and that's when I wrote the songs for this record," Olson says. "When they were done mixing that record, the engineer had something going on for a week, but then he had another week off, and that's when I booked him to come here."
Of course, the Creekdippers' album was also supposed to be called "Someone to Talk With," but that changed as well.
"I thought 'Someone to Talk With' had too many connotations," says Olson of the name switch. "I went to 'My Own Jo Ellen,' which seemed a little more individualistic notion, and I thought it tied the whole record together."
"My Own Jo Ellen" started out like most Creekdippers albums when it came time to record, but Olson decided to shake things up slightly with one simple maneuver.
"What we've done in the past when I've come up with a few songs, I'll call up Razz and book him for about 10 days," says Olson. "That's what I did this last time, but I thought 'Why don't I book an engineer and a drummer and some other people?' So, I did that. It's basically you get that time when they're all here, and you have to get something done."
If there is a vibe of spontaneity evident in "My Own Jo Ellen," it is there by design. As in the other Creekdipper projects, Olson waited until Razz was in the studio to teach him the songs written for the album. The difference this time was the presence of other musicians who also had to learn the material.