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Gregory Alan Isakov has been performing or recording with big names this year – Ani Di Franco and Brandi Carlile. He’ll bring his poignant lyrics and acoustic guitar to One Longfellow Square on Saturday.

IF YOU GO

GREGORY ALAN ISAKOV & THE FREIGHT WITH NICOLE REYNOLDS

WHEN: 8 p.m. Saturday

WHERE: One Longfellow Square, 181 State St., Portland

HOW MUCH: $12 (advance), $15 (at the door)

CONTACT: 761-1757; onelongfellowsquare.com

Gregory Alan Isakov looked like he could have been riding the rails during the Great Depression alongside Woody Guthrie. The 29-year-old wore a short-brimmed cap, a navy blue workman's shirt, brown pants and shabby leather shoes. The small, handsome young man had dark stubble on his face.

"This song makes me happy," Isakov said with a boyish grin to the rapt audience of about 300. "Sad songs make me happy."

The acoustic-guitar-and-harmonica-wielding musician performed -- mostly with eyes closed tight -- earlier this month at Everyday Joe's Coffee House in Fort Collins, Colo. It's a giant java shop that doubles as a church.

The singer-songwriter's haunting, hushed vocals inhabited every space of the room. Isakov sang poignant, gorgeously detailed songs about life on the road, cherished childhood memories and the wonderful vagaries of love.

He finished his 45-minute set, and enjoyed a standing ovation. Most selections were culled from his latest album, "This Empty Northern Hemisphere" (available on CD and vinyl).

Isakov lives in nearby Boulder, Colo. The state's two most important publications, the Denver Post and Denver Westword, rightfully heralded "This Empty Northern Hemisphere" as a masterwork.

National publications have taken notice as well. In August, Paste Magazine profiled Isakov for a feature dubbed "Best of What's Next 2009." On Sept. 12, Isakov shared the main stage with M. Ward, Girl Talk and the Yeah Yeah Yeahs at Monolith Festival at Colorado's famed Red Rocks Amphitheatre. He then performed nine dates through the Midwest with folk heroine Ani DiFranco, who became a fan after playing an Aspen date with Isakov in July.

"She just really liked us and has been really nice to us," Isakov said the day after the Fort Collins show. "On the tour that just ended, we got to talk for a while. She's brilliant, and I really appreciate her personality -- there's no difference between how she is on stage and off stage."

Isakov also counts Brandi Carlile -- the gifted singer-songwriter who had a hit in 2007 with the title track to her album "The Story" -- among his burgeoning legion of fans. On "This Empty Northern Hemisphere," self-released by Isakov just like his previous three discs, Carlile sings harmony on four tracks.

On the closer, a killer cover of Leonard Cohen's "One of Us Cannot Be Wrong," the two artists deliver a moving duet.

"It was a cool thing, because Brandi and I are both big Leonard Cohen fans, and I don't think she had heard that one before," Isakov said. "It's one of the most beautiful love songs."

Readers might recall Isakov performing the Cohen song with Carlile in April at the South Portland Auditorium. (Watch the stirring performance on YouTube: www.youtube.com/watch?v=dMij1JcQBPg). The pair also performed a winning version of the Patsy Cline hit "You Belong to Me." (Also found on YouTube at www.youtube.com/watch?v=sedCAJFQrQ8&feature=related).

That April gig led to Isakov's upcoming headlining date on Saturday at One Longfellow Square, where his band the Freight will accompany him.

"I love Portland; that was one of my favorite shows," Isakov said with genuine enthusiasm. "It was weird, I felt real normal there. It was a great place with nice people.

"I just felt so well-received -- and normal."

Wade Tatangelo is a freelance writer based in Fort Collins, Colo., whose work has appeared in publications nationwide. He interviewed Ani DiFranco for the Portland Press Herald in April.