Monterey Americana Music Fest boasts buddies in Dwight Yoakam and Jim Lauderdale.

When the headliners for the Monterey Americana Music Festival arrive this weekend, they’ll bring two of the strongest resumes in the genre with them.

Dwight Yoakam has sold more that 25 million records and earned a place on Billboard Magazine’s Top 25 Country Stars of the past 25 years—and scored memorable performances in films like Crank and Sling Blade.

Grammy-winning singer-songwriter Jim Lauderdale has been championed by the Americana Music Association since the organization began giving out awards back in 2002: He won the AMA’s first Artist of the Year and Song of the Year—“She’s Looking at Me” with Dr. Ralph Stanley and The Clinch Mountain Boys—and has hosted the show himself the past 12 years.

“It’s amazing to be on stage with iconic musical figures and folks I’ve idolized my whole life,” he says. “And I get to see a lot of the fantastic new acts. It’s just full of amazing artists.”

Yoakam is one of those iconic figures Lauderdale is speaking of. Yoakam picked up the honor for the 2013 Artist of the Year.

Now Yoakam and Lauderdale, who came out of the same cowpunk music scene in mid ’80s Los Angeles, look forward to catching up Saturday at the Fairgrounds. (Antsy McClain and the Trailer Park Troubadours, Hollow-Wood and Casey Frazier also perform.)

But it will be more than a chance to chum around: It will be an opportunity to renew a friendship that has driven some of the better country rock collaborations in a generation. Lauderdale, in fact, sang harmony on some of Yoakam’s earliest albums.

“I love Jim and his sense of humor,” Yoakam says. “We have a pick-it-up-where-we-left-off-five-years-ago thing going on everytime we see each other.”

When describing how something like that happens, Yoakam grows both poetically concrete and a little abstract.

“The key to having a successful [musical relationship] is not trying to force it,” he says. “It’s really born out of genuine fondness for somebody and admiration of their talent. I’ve always admired Jim’s indirect directness.”

Lauderdale believes openness is key with whoever you’re collaborating with, and a crucial tool in getting “a hold of whatever it is that’s trying to be expressed and grow the song, whether you’re writing together or you’re doing the harmony.”

Back when the Los Angeles Americana/“cowpunk” sound was emerging, Lauderdale appeared on Lucinda Williams records and no fewer than five of Yoakam’s albums. But his philosophical connection stretches back further.

“Dwight’s been an inspiration for me through the years,” Lauderdale says. “I remember listening to his first album over and over again. I was so taken by his songwriting.”

For Yoakam, winning AMA’s Artist of the Year provided great affirmation, but more importantly, it honored the music he and Lauderdale, and others like Los Lobos and Social Distortion, were doing in L.A. 30 years ago.

“The album came full circle to where I began at college radio and alternative radio,” Yoakam says. “[The award] was really a credit to everyone who worked on the album. I accepted it as an acknowledgement of that.”

Beck was among them, co-producing two tracks on Yoakam’s most recent album, the heavily touted 3 Pears.

After the two musicians repeatedly crossed paths over the years, Yoakam thought that Beck may be the ideal person to collaborate with.

“[Beck] came to the office and we sat and talked for a while,” Yoakam says. “We ended up doing it and it was very kinetic and very spontaneous—he just responded to what I was doing.”

“A Heart Like Mine,” recorded entirely in Beck’s home studio, is a retro honky-tonk, complete with reverb vocals. It too channels Yoakam’s early years, playing dingy Los Angeles punk clubs on bills with the likes of The Blasters and X.

The spontaneous and engaging “Missing Heart” also harkens back to an era when, according to Yoakam, “country music used to have a very edgy rock and roll energy.”

“They used to call the scene that broke out of L.A. in the early ’80s ‘cowpunk.’ But I never really did it myself,” Yoakam says. “I was doing neo honky-tonk music, and it had a certain rock attitude. I think ‘A Heart Like Mine’ is cowpunk—it’s got emotional candor, I hope.”

Then there’s “Waterfall,” which is best described as a romp with a childlike rhyme scheme played on a three-quarter-size guitar.

“That guitar makes me write some funny lyrics,” Yoakam says.

An example: “If I had a jellyfish, I betcha we would never miss/ A single peanut butter kiss or squeeze.”

But with seemingly everything Yoakam writes—even his silliest—there’s deeper meaning.

“The chords and bridge deal with the loss of innocence,” he explains. “Then there’s the hope that innocence can overcome loss and find its way back and not become too esoteric.”

Lauderdale is readying to release I’m a Song this Tuesday, July 1, and it may prove to be his opus. It’s his whopping 27th album—as well as his first double album. The musician recruited an all-star cast of guest performers and guest songwriters, including longtime pal Buddy Miller, Grateful Dead lyricist Robert Hunter, renowned pedal steel player Al Perkins and the incomparable Elvis Costello.

Lauderdale first discovered the Dead in high school, after hearing Workingman’s Dead.

“I was hooked,” he says.

So teaming up with Hunter on six records—a mutual admiration for bluegrass great Ralph Stanley brought them together—came naturally. Lauderdale estimates that they’ve written close to 100 tunes together thus far. Last year, they released a pair of records—Lauderdale also released an album with the North Mississippi Allstars.

While some might take a breather following the release of a double record, Lauderdale’s not among them. He and Hunter have a bluegrass record in the works and a couple of country albums already in the can, ready for release when his label gives the go-ahead. A record with British singer-songwriter Nick Lowe is scheduled to hit the streets some time this winter.

He’s also gearing up to begin recording more content for the Buddy & Jim Radio Show on Sirius XM. Over the two years it’s been in existence, Miller and Lauderdale have curated sweet playlists and interviewed everyone from Ry Cooder to Emmylou Harris.

Yoakam is at the top of Lauderdale’s list of guests to have on soon. Surprisingly, they first heard they’d both appear at Americana Fest from the Weekly. It’ll come as no surprise they were both thrilled with the news.

Monterey Americana Music Festival happens 9am-7pm Saturday, June 28, at the Monterey County Fairgrounds, 2004 Fairgrounds Road, Monterey. $30; $45; $60; $65; $75. 915-8044, http://montereyamericanafestival.com.

Monterey Americana Music Festival slims down while going bigger.

Festival producer/founder Dan Miller had one goal: Create an event with potential to become an annual Monterey tradition.

Americana Festival’s debut—featuring Jason Isbell in the headlining slot—yielded a light turnout. But Miller never let it suck his steam.

“There was some stuff I could’ve done that would’ve brought more people, but it’s a learning experience,” he says.

This time around, the Pagrovian pared the event down to a single day and booked the artists himself instead of trying to delegate the duty. He also brought in former Herald music editor/guru Mac McDonald to consult and went more for name recognition than critical acclaim, which shows with a caliber of performer like Dwight Yoakam, secured as headliner. Here’s the rest of the less-is-more lineup:

Casey Frazier 10:30-11:15am

Hollow Wood 11:45am-12:45pm

Jim Lauderdale 1:15-2:30pm

Antsy McClain and The Trailer Troubadours 3-4:30pm

Dwight Yoakam 5-7pm