Conor Oberst (photo: Joshua Huver)

Conor Oberst convinced his friends to stick around Hardly Strictly Bluegrass Festival an extra day for a special engagement at The Fillmore on Saturday night, October 1.

One day after commanding the lineup at the festival’s Rooster Stage all day on Friday, Oberst brought Miwi La Lupa and Jim James of My Morning Jacket for an encore performance indoors a few short hours after the festival had wrapped up for the day.

Oberst even convinced M. Ward to show up early and stay late to twice perform a pair of songs from their 2009 folk supergroup collaboration with James, Monsters Of Folk. Ward closed out The Porch stage on Saturday, and put in overtime when he appeared onstage at The Fillmore for the highlight of the night.

Oberst was in typical form, taking his role very seriously (as evidenced by his corduroy jacket). The banter between songs was as entertaining as the revisited Bright Eyes songs were nostalgic. Dancing a thin line between dangerously foreboding and hilariously dark, it’s best to simply laugh along with his self-deprecating humor.

He joked at length about being out of money and expressed confidence in “his boy” Donald Trump. At one point he admitted his disdain in the future grows every day. There were plenty of mixed emotions in the room, but then again, that awkward and confused energy is from where Oberst draws some of his most compelling points, and his delivery was as fierce and poignant as ever.

Kicking the evening off proper was Miwi La Lupa at 9pm sharp. At first they seemed dwarfed by the wide stage setup of James and Oberst, but it did not take long for their sound to make up for their compact arrangement, revealing a powerful four-piece roadhouse group.

They have been in the Bay Area all week prepping for their record release party on Monday, October 3 in Los Angeles. There were few frills in La Lupa’s straight-to-the-point jaunts through the human psyche, including the new album’s title track “Beginner’s Guide” — specifically, in the way a monotonous vocal part is built up over a military snare beat and haunting guitar chords are torn apart note by note in increasing tempo before the whole thing disintegrates itself into a cacophony of shouts, noise, and feels.

James’ band was set up and ready to go fifteen minutes later, almost immediately after Miwi and co. had finished clearing their gear. For fans that caught The Fillmore performance as well as the daytime set on Friday, the fact that the same seven songs were repeated (albeit in a different order except for closing with “State Of The Art”) mighgt have been offputting, if it weren’t Jim James we were talking about.

The eight-song set was bookended by two tracks from his previous solo release, 2013’s Regions of Light and Sound of God: “A New Life” and the ultra-high energy sing along “State of the Art (A.E.I.O.U.)” and also included the album’s cut of “Know Til Now.”

Peppered between Regions songs were selections from the first half of his newest effort Eternally Even, out November 4. Leading into the track “Same Old Lie” James took a moment to address the crowd.

“It’s hard to believe it’s already Thanksgiving,” he said. With sunglasses over his eyes and a second pair hanging on the collar of his T-shirt, it wasn’t out of the question that he might not be all there. “I’m thankful for all of you, all of my friends, and I am especially thankful for Conor, my dear ol’ beautiful pal, he’s so good at bringing people together. I don’t know if he’s even here right now, I’m just so stoked he had us here.”

Stand out tracks included “Same Old Lie,” which saw James adding color on a keyboard before the song delved into a jungle jam that reeked (in the best way) of Kasabian trying to do The Doors, and “Here In Spirit,” both off of Even. Following “Spirit,” James gave a near-identical monologue, leaving plenty of confused looks throughout the crowd as he pushed the band into the final song of the set.

For as grateful as the crowd seemed with how quick James’ turned around after Miwi La Lupa’s set, Oberst seemed rueful, taking nearly 45 minutes to set up. But it was worth every aching second — most of the crowd spent the time catching up about their opinion of Hardly Strictly earlier.

Oberst took the stage just before 11:15 with his usual awkwardly assertive command of the crowd’s attention, and wasted no time getting on with the music. He began the first of many furiously strummed muted introductions on his acoustic guitar, and nearly every time the audience was faked out for “At The Bottom Of Everything,” which was never even played.

Instead, there was a 16-song set that spanned multiple points throughout his career. Oberst kept his focus on the more recent end of the spectrum, including four tracks from his upcoming album Ruminations as well as a few one-off songs that haven’t landed on any records.

Oberst has not lost any of his sharp wit or hot-fire speech, often succumbing to an intense volume of emotion in nearly every song, resulting in flying spit, picks, and broken guitar strings throughout. Ahead of “Bowl Of Oranges” from Bright Eyes’ 2002 breakthrough album Lifted, or The Story Is In The Soil, Keep Your Ear To The Ground, Oberst had a few words for the crowd.

“This really has been a great weekend and I hope we get invited back often.” Oberst said. “I’m so pleased with my friend Jim, you guys. What really impressed me was how he thanked me, twice.”

Following “Bowl,” Oberst’s backing band (save for his bass player) left the stage for a very heavy delivery of emotional guilt in “You All Loved Him Once” off of the upcoming Ruminations. The song ends on a snarky line full of contempt: “Imagine that,” an enormous wad of spit onto the front row was the only thing that kept it from a dry delivery.

“It’s been so touching to have my dear friend Jim with me this weekend. I really feel like he means it and he doesn’t mean a lot of the things he says,” said Oberst before rambling into an apparently unrelated tangent. “Have you guys ever played ‘Would You Rather?’ Like, would you rather get sprayed with a fire hose of semen or sit in a tub of menstrual blood? I don’t know. Both…are equally interesting.”

The band jumped back into the music with “Desert Island Questionnaire” from Oberst’s 2014 solo release Upside Down Mountain and “Take It Easy” from Bright Eyes’ 2005 release Digital Ash In A Digital Urn.

Ahead of welcoming James back to the stage with M. Ward for two Monsters Of Folk songs (“Say Please” and “Whole Lotta Losin’”), Oberst continued to welcome sideways glances and gaping jaws among bursts of laughter as he compared the 2009 super-group to The Beatles.

Oberst wound down with two more tunes from the upcoming record, “A Little Uncanny,” “Till St. Dymphna Kicks Us Out,” and then “Breezy,” the lone tune from 2012’s One Of My Kind before ending the set just after 12:35am. To close “Breezy,” Conor and his band exited one by one until only the violinist and second guitarist were left to close the melody.

Between 12:40 and 1am, Oberst managed to squeeze in three more tunes to close the evening proper: “Cape Canaveral” from his self-titled solo effort in 2008, “Train Under Water” from the 2005 Bright Eyes album I’m Wide Awake, It’s Morning and a newer song that was not included on the Ruminations track listing called “Napalm” which saw Miwi La Lupa join on percussion.