Having previously teamed up with the likes of Pink Martini, Blind Pilot, and Storm Large, the Oregon Symphony has laudably and successfully used local crossover performances to reach a younger audience, but I should have realized I was in for a slightly awkward evening merely from how oddly laughable—maybe even slightly patronizing?—it felt just to see the word “Indies” on the Schnitzer’s bright downtown marquee. And once inside the venerable performance hall, it was clear that the blend of these two musical worlds would occasionally feel a little forced. Both the promotional material for the show and its on-stage introduction kept referring to the Oregon Symphony as a “band,” which felt a bit like an enthusiastic high school English teacher trying to convince disinterested students that Shakespeare was a rapper. It was probably the first time the phrase “shout-out” has ever been used at a Symphony performance (and hopefully the last).

Despite the inevitable awkward moments, though, the Symphony’s celebration of Portland’s still thriving independent music scene (no need to be modest) turned out to be thoroughly entertaining evening of music that offered a chance to see both the orchestra and the acts it invited on stage in intriguingly novel settings.

Singer and composer Holocombe Waller took the most advantage of the drama the Symphony can lend a performance, to somewhat mixed effect. He has a powerful and elastic voice that had no trouble standing up to the dynamic range of the orchestra. That said, Waller’s music already teeters precariously on the line between theatrical and overwrought, and the symphonic backing doesn’t make this balancing act any less difficult. Whether this works in his favor depends on how you feel in the first place about the more histrionic moments in his songs. Either way, though, it’s hard not to respect an artist like Waller, with a clear vision and the obvious ability to manifest it, essentially going for broke. That’s especially the case when he’s successful, as he certainly was when premiering an excerpt from his new song cycle, Wayfinders. That bodes well for the cycle’s debut performance at Alberta Rose Theater on November 22.

Mirah might have at first seemed the most out of place of the three acts to grace the Schnitzer’s stage. Her music is arguably the most understated, and though she has a lovely voice, its timbre isn’t quite as suited to projecting over the swells of a full orchestra. But Mirah knows how to quietly charm a crowd: a story about her mom coming to a show in a punk house and cleaning the neglected stove was an amusing and endearing juxtaposition with the impressive setting in which she found herself on Saturday, even if it left some of the older Symphony regulars near me muttering in bewilderment. Most importantly, though, Mirah writes lush and inviting songs that felt even more comfortable and lived-in with the Symphony’s contribution. Once the music got going, there was nothing out of place about it.

Black Prairie closed out the show, their pastiche of folk, bluegrass, klezmer, and other eastern European music by far the most naturally augmented by the orchestra. Perhaps the highlight of the evening was the band’s closing song, “34 Wishes: The Legend Of,” a rollicking composition by guitarist Jon Neufeld and Dobro player Chris Funk that put the orchestra through its paces. The Symphony, and conductor Jeff Tyzik, looked to be having just as much fun as Black Prairie were.

Ultimately, the night gave three Portland independent acts the chance to stretch out and experiment with a wider palette than would normally be at their disposal, and it was an opportunity that all three clearly relished. The pleasure of seeing that alone was worth a bit of awkwardness.