COTTAGE GROVE — Browse through the discography of The Jack Maybe Project and one thing quickly becomes obvious: This band has a lot of songs about monsters, and these particular monsters are animated caricatures who play musical instruments.

“A lot of the songs I write are sad, so I try to put cartoonish faces on them to make them more palatable,” guitarist Jack Maybe said Saturday night, March 6, during a set break at the Axe & Fiddle. 

“Our next album is all about fighting or accepting those demons or monsters in our life.” 

The band’s third release, “True Names,” is due out in October, and The Chronicle attended what would be one of the last concerts for anyone – performers or music fans – before stay-at-home orders were put in place.

As you might have guessed, “Jack Maybe” is a stage name. With good reason. 

“We used to be ‘The Obtuse,’ but nobody liked that one. I have a very unusual first name — Trinh — so we couldn’t go that route. So I just started saying Jack all the time. It was a lot easier,” said Maybe, whose real name is Trinh Youngman.

Like so many of today’s bands, The Jack Maybe Project finds it difficult to put a label on its music. It’s sorta folksy. It’s kinda jazzy. It has a nice flow. It’s just a delightful blend of complementary styles.

“A fellow musician told me that we’re the American songbook,” Maybe said. “Just a bunch of different versions of Americana all blended together.”

Maybe was classically trained, earning his master’s at Portland State. He plays stand-up bass in another band, “Kiki & the Dowry,” and also is proficient at playing banjo, ukulele, mandolin, bass and violin. He says he started learning rock ’n’ roll songs when he first picked up a guitar.

“Then I started listening to Paul Simon and it threw me into a whole different world,” he said.

The band got perhaps their biggest applause of the evening after two of their covers, “Will the Circle Be Unbroken” and a stirring version of “St. James Infirmary.”

Their latest release, “Weary Bones & Witchcraft,” is spellbinding, “Sympathy From the Devil” sounds nothing like the Stones’ similarly named song, but it’s as catchy. The Jack Maybe Band’s intricate melodies and harmonies really shine through on “River Monster” and “Monster Blues in G.”

Maybe and vocalist Bry Sawyers are the only two band members who have been there since Day 1. On the night we saw them, they were joined by clarinet player Brooke Friederichs and drummer Dennis Eash. At other shows, they have banjo, trumpet and trombone players chiming in. 

Friederichs’ presence was evident, as her masterful clarinet playing took center stage on more than one occasion.  

“Our horn section is tip-top,” Maybe said. “I always secretly wanted to be a horn player, so I’m happy to have them here supporting me.”

As Maybe creates his monsters, he visualizes which instrument each creature should play. So far, there hasn’t been any infighting over who gets assigned to which monster. 

Bigger bands have broken up over smaller dust-ups, y’know.

“I do the booking, I do the marketing, I do all the work. They just have to show up and practice and play, that’s it,” Maybe said. “I’m trying to minimize all the band’s drama.

“Yeah, I call the shots, but I don’t intrude either. I give people freedom to explore.”

Another oddity about Jack Maybe: He wears one brown shoe, one black shoe.

Whatever Maybe is doing, it’s working for him and his band.

Definitely.