On tour with Stapleton, Brent Cobb’s career seems to be on the right path.

Brent Cobb is traveling what you might call a favorable path. Having released two albums of sterling, Southern-drenched country and soul tunes in just over 16 months, the Georgia-born songsmith is heading to Lexington this weekend to perform on some rather fortuitous turf.

He starts by playing an in-store gig Saturday afternoon at CD Central, the same local record store that, on a Sunday afternoon in May 2015 (Mother’s Day, in fact), hosted a show by another country traditionalist by the name of Chris Stapleton. That evening, with the help of Marty Stuart and has Fabulous Superlatives, Cobb will hit Rupp Arena for a performance headlined by Kentucky-born megastar Stapleton for what is, from top to bottom, the strongest country concert bill to play Rupp in recent memory.

But the sense of perspective isn’t lost on Cobb. In one day, he will play the first Lexington venue Stapleton visited in the wake of his Grammy winning 2015 album “Traveller” as well as the downtown big house that, judging by the evening show’s sold out status, isn’t big enough to accommodate Stapleton’s current fanbase.

“That’s pretty cool,” Cobb said of the parallels and contrasts of the two Saturday shows. “When you see it work for somebody that you respect, you try to take notes and learn something. Chris has been a superstar to a lot of folks where you’re from in Kentucky. But to folks like me, who have known him as a songwriter for the last 10 years on Music Row, Chris has been putting out great songs for a long time. Still, it’s been pretty neat to see everything top out for him like it has.”

There is another, more directly musical link, as well, between Stapleton and Cobb. Both artists share the same producer: Nashville/Americana song stylist Dave Cobb, the Georgia songwriter’s cousin.

The working relationship between the two Cobbs extends back to when Brent Cobb cut his debut album, “No Place Left to Leave” in 2006. The album took the singer to the decidedly non-country terrain of Los Angeles, where Dave Cobb co-produced the album with Shooter Jennings.

“It was a little bit of a culture shock,” Brent Cobb said. “Working with Shooter and Dave, separate from the environment of LA, felt like something out of a movie. It felt like something out of a story you just dreamt up. The environment of LA sort of added to all that. It was just like, ‘Whoa, man.’ I just didn’t plan on that. Yeah, it was pretty surreal.”

Fast forward a decade, with both Cobbs working in Nashville. There, a more natural storytelling voice was put on display for 2016’s “Shine on Rainy Day” and 2018’s “Providence Canyon,” records that more accurately depict the rural inclinations, situations and characters of the present day Brent Cobb.

“It was like coming home,” he said of the newer records. “I had been trying for us to get back together on an album, but it just never really made sense. When I moved to Nashville, Dave was still living in LA. I was writing and working with other people. But I always, in the back of my mind, looked forward to being able to get back with Dave. Then when the opportunity presented itself, that’s what I did.”

Of course, being tour mates with Stapleton and Stuart for over a year, which has regularly placed Cobb in front of sold out arena and amphitheatre crowds, hasn’t exactly hurt in establishing the Georgia country journeyman’s no frills musical profile.

“To be able to see 20,000 people show up every night for two years in a row just gives me hope that, ‘Alright, we can get to that point to where people come out to hear regular ol’ music,’ which is what Chris and Marty play. It’s regular ol’ music. It’s just nice to know that so many people still care about that because it was getting a little hard to tell there for a little while.”

IF YOU GO

Brent Cobb

When: 1 p.m. Oct. 27

Where: CD Central, 377 S. Limestone

Admission: Free

Call: 859-233-3472

Online: cdcentralmusic.com, brentcobbmusic.com

Chris Stapleton

Opening: Marty Stuart and his Fabulous Superlatives, Brent Cobb

When: 7 p.m. Oct. 27

Where: Rupp Arena, 430 W. Vine

Tickets: Sold Out

Call: 859-233-3535

Online: rupparena.com