Oldham was also thrilled to have a chance to interact with these older, more established musicians. "They were hilarious," he remembers. "They have a funny phrase that they kick about, which is - whenever a session musician plays on somebody's final session or final show - they say that they killed him. So one would be, like, 'I killed Johnny Paycheck.' They'd bring that up once or twice a day, where someone would bring up who they'd killed."
Nevertheless, as odd as legends like Johnny Paycheck could be, it still must have been strange for these seasoned veterans to work with an enigmatic alternative rock figure like Oldham.
"I knew that while they were there, that they were definitely straddling the line between having a good time and questioning what the hell was going on," Oldham jokes.
But in the end, Oldham saw this opportunity to redo some of his past material in a completely different context, as the chance of a lifetime.
"The goal of this record was that I had at least a window of opportunity - that I didn't know how large it would be - to do a session like this. But like I say, I didn't want to do it with new songs because I'm obsessive with new songs, and I didn't want to obsess with these people that knew exactly what they were doing - at least not until I'd done a session with them once. Now I feel like I could ask one or two of them, or even the whole bunch, to work with me on new songs, perhaps. I don't know if I will, but I could because I know how it works. But not knowing how it works, I had no desire. At first I was thinking of doing just a covers record of other people's songs. But then I thought I might as well kill two birds with one stone and rerecord these old songs."
Besides music, Oldham also has an acting career. But unlike many other musically minded actors, Oldham was an actor before he became a recording artist, rather than the other way around. His credits include the TV movie "Everybody's Baby: The Rescue of Jessica McClure" and the 1987 John Sayles film, "Matewan."
But Oldham sees acting as just one of his past professions and one that holds little allure for him today.
"Pretty much music has replaced acting," he says now. And does he miss it? "Not so much," he admits. "I don't think about it that often. I think about it more if I'm out here (in Hollywood)." Making music is simply fulfilling for Oldham, which is a benefit he never expected to receive from his acting endeavors. "(This is) mostly because the actor is so dependent on so many other people," he explains. "Just to figure out if, and when, they're going to work. If I need to work for four or five hours tonight on something, I have something to work on. Whereas, if I'd just finished a job - an acting job - I would be dependent upon whether or not there was another acting job coming up. (With music) there are just more places to put your energy."
And speaking of LA-LA-Land, tinsel town is not at all one of Oldham's favorite tour stops.
"I don't like playing LA all that much. I like being here more than I like playing here. We played an in-store last spring at Rhino Records, and that was so much more fun than the last couple of times we played (actual concerts) in Los Angeles."
Quite naturally, then, some of Oldham's favorite places to tour exist a little bit outside of the main media capitals.
"I like playing San Diego," he says. "Over the last few years, we've started trying to play smaller cities in between big cities. We've been active in seeking out places in order to do that just because it's so much more fun. We did a trip up and down the West Coast a couple of years ago. And then last year, we did a trip up and down sort of the next set of states over: Arizona, New Mexico, Colorado, Utah and then Eastern Washington, Oregon, Idaho, Western Montana. Just to play Moscow, Idaho, Walla Walla, Wash. and big cities like Salt Lake City and Denver and small cities like Durango, Col."
It's hard to predict if the sound of "Greatest Palace Music" will help Oldham make more inroads into mainstream country music circles.
But even if this latest work doesn't create a large new audience for the performer, Oldham will always have one especially shining moment with a country music legend to forever savor; one that nobody can ever take away from.
Oldham had the great fortune to sing a duet with Johnny Cash on his own song, "I See A Darkness," for the "Solitary Man" album. He recalls this recording experience as being something quite surreal, to say the least. "I remember it was as if I was a color form or a paper doll that had just been pasted into the situation."
In reality, however, Will Oldham definitely is the real deal.