As it turned out, Chesnutt did record three songs Jennings made famous — “Only Daddy That’ll Walk the Line,” “Are You Ready for the Country” and “Freedom to Stay.”
He included two selections each from albums recorded by Kris Kristofferson, Willie Nelson and Hank Williams Jr., including Kristofferson’s “Lovin’ Her Was Easier (Than Anything I’ll Ever Do Again)” and “Sunday Morning Coming Down.” Nelson is represented by “A Couple More Years” and “Bloody Mary Morning” and Williams by “Whiskey Bent and Hell Bound” and “Country State of Mind.”
Doing an album of covers wasn’t something Chesnutt had planned. He says Pete Anderson, who made his name in the ’80s as Dwight Yoakam’s producer and guitarist, approached him with the idea on behalf of Saguaro Road Records.
“The guys at the label decided to do an Outlaw-themed album,” Chesnutt explains, “and they gave it to Pete to pick the artist and put it together. I was the first artist he thought about.” Then, with a laugh, he adds, “That’s what he told me.”
Chesnutt says he had met Anderson once in Switzerland but had never worked with him.
“I went out there to L.A. to meet with him,” Chesnutt continues. “We sat there and talked about the different songs. Everybody had a list. I had a list. Pete had a list. The label guys had a list. There were four or five lists.
“Pete and I picked through everything with a couple of acoustic guitars. And we came up with the songs that best suited me. We had to keep it down to 12 songs — or this album would have had six discs. … We had to pick songs that really made the Outlaw statement. We didn’t want to be obvious and cut songs like ’Good Hearted Woman.’ We wanted to get a little deeper than that. That’s why Kristofferson’s songs came up.”
The recording, done at Anderson’s studio in Burbank, Calif., went quickly.
“I did my part in two nights,” he says. “We already had the arrangements. We’d already sat down together and worked that out. I flew up in December to do two nights of track vocals, and he was going to build around that. Then I’d [planned to] come back later in January and lay down the real vocal tracks. But Pete’s tracks were so good, I ended up doing all the vocals during the [time set aside for] track vocals.”
One of the album’s highlights is “A Couple More Years,” on which Amber Digby sings with Chesnutt. It is the only cut that features another vocalist.
“I’d known about Amber Digby for years,” he says. “Since satellite radio. Since Willie’s Place [a channel on Sirius XM] came along. They play her on there all the time. I’ve never met her, but I love her singing. When she agreed to do this, I was really excited about it.”
The two still haven’t met, but their performance sounds like they’ve sung together for years.
“She did her part when I couldn’t be there,” Chesnutt laments. “I already had the entire song cut. She came in, and Pete put her in there with the magic of the buttons. It’s really cool the way our voices blend.”
Although he has long incorporated Jennings’ songs in his concerts, Chesnutt says he had never performed the Kristofferson songs. “I’d never rehearsed them. I’d never sung them at the clubs because I didn’t consider them my style until I recorded them. … I wanted to do them justice, so I just quit listening to [the originals] and did the songs from the songs’ standpoint.”
“We’re all out there together at the same time,” he says. “We start the show together. We sing in rotation and harmonize together. We tell stories and pick on each other. It’s like we’re just sitting around having a guitar pull.”
That’s the same kind of intimacy Chesnutt brings to Outlaw.