The first time I interviewed Gregory Alan Isakov, we were at his apartment in Boulder. It was nine and a half years ago, on the eve of his first concert with the Colorado Symphony. Back then, he exuded a combination of confidence and humility, honored to be collaborating with such an esteemed ensemble, but he was also matter-of-fact about getting the gig done.
But that wasn’t the whole story.
“I remember that first time we played with them,” Isakov said in an interview last week, this time just a few weeks out from his third outing with the orchestra, which is set for later this month. “We were so nervous.”
“We were like, ‘Are we dressed OK? Are we too loud? Oh, and I’m sorry my songs are all in C.’ ”
The concert turned out to be a critical success, as well as a crowd-pleaser, despite the obstacles of combining Isakov’s casual, folk-influenced musical style with the orchestra’s centuries-old formality. The event changed the trajectory of both parties.
Isakov and his band used those same complicated arrangements to launch a career of orchestra gigs. Since then, they have played with 20 different symphonic ensembles across the United States, turning the concerts into a second track of a touring schedule that is set mostly in nightclubs and arenas.
And the orchestra used the moment to seal its reputation as one of the foremost classical collaborators with pop acts, which has been a crucial part of its financial strategy for a decade now. Isakov and the orchestra even went on to record a popular album together in 2016 featuring the best arrangements of the bunch. Fans of both the orchestra and the singer-songwriter seem to come together organically for their duets. Both of this month’s back-to-back offerings at Boettcher Concert Hall sold out quickly.
As for all that nervousness, Isakov said, things are easier now. Though taking the stage with dozens of classical musicians and a conductor does come with challenges distinct from the concerts that showcase only the handful of musicians in his band.
“They’re not just our songs being backed up the way we play them every night; we’re definitely playing them differently,” he said. “With the band, we’re just so psychic with each other; we just play.”
But orchestras perform with scores. They are not exactly free-wheeling, and the band has to stay in sync. It’s all about listening.
“We hear the violins first. They’re right behind us. Then we’ll hear the brass a little bit after that,” he said. “You have to listen so hard.”
“Everything is little lagged up there so we have to be really smooth with our timing,” he said.
Fans who attend the concerts will hear some familiar fare, and it will likely include “Amsterdam,” which Isakov lists among his favorites in the pairing. The arrangement uses a lively backdrop of strings to heighten the emotional resonance of the original, which is also punctuated by smooth, sonic endpoints from woodwinds and brass.
He also likes “Master & a Hound.” The orchestral arrangement starts out with a gentle guitar intro similar to the version first recored on Isakov’s 2009 album, “This Empty Northern Hemisphere.” But then woodwinds join, followed as the piece progresses by the rest of the orchestra, evolving toward a dramatic crescendo that outdoes the emphatic ending of the original.
Isakov said it is one of the more difficult pieces to pull off with its “elusive downbeat.” His band planned to play it the first time it performed with the orchestra in 2013, but Isakov pulled it at the last minute because he just wasn’t sure it was ready.
The band and the orchestra have since added it to their repertoire, and the song is one of the highlights of their joint recording.
The concert also will feature updated arrangements of existing collaborations. “Sometimes there’s a little bit more woodwinds. Sometimes there’s a little bit less,” he said. “We are still finding those moments where we can perfect it a little better.”
There will also be some new songs, including a fresh arrangement of “Chemicals,” from Isakov’s 2018 album “Evening Machines,” a piece the pair have not previously performed together.
Speaking of new material, Isakov expects to release more of it in the coming year. He has recored a considerable 35 songs, he said, and has chosen 11 so far that he expects to release sometime in the spring.
There is already a plan to develop orchestral arrangements of the material, and Isakov hopes to bring it to Denver soon. The city is where that part of his performing routine started, and it is an especially comfortable place to play.
This time around, no one is likely to ask if they’re dressed OK or apologize for anything. But, Isakov said, the experimenting with new ways of producing his songs will continue.
“The coolest thing is that it feels like the crowd, the symphony and the band are all in this together. The crowd is even sort of like ‘Is this gonna work out?,’ ” he said.
It’s a safe, and hometown, space. “There has never been a train wreck, but if there was, it would be totally fine.”
IF YOU GO
Gregory Alan Isakov performs with the Colorado Symphony Aug. 19-20 at Boettcher Concert Hall in the Denver Performing Arts Complex. Info: 303-268-3639 or coloradosymphony.org.
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