For more than two decades, singer-songwriter Will Sheff — through his creative vehicle Okkervil River — has been sketching out characters fighting, clawing and scrapping against the burden of existence. He is a master of crafting multifaceted personas who strive to find meaning and connection in an inevitably fated journey.
Sheff has returned time and again to that E.M. Forster theme of “only connect.” He explored it through the lens of addiction and familial discontent (“Black Sheep Boy”), the corrosive nature of fame (“The Stage Names”) and the uneasy nature of nostalgia and homecomings (“The Silver Gymnasium.”)
And after nearly two years of not connecting to audiences, at least not in person, Sheff is returning to the stage to delve into the mysteries that motivate humanity.
“In 2019, we were sort of walking across a thin layer of ice over a lake that was about to crack underneath our feet, and we were calling that normal,” said Sheff, who will join singer-songwriter Damien Jurado at the Starline Social Club in Oakland Dec. 3 before debarking for two shows at the Henry Miller Library in Big Sur the next day.
“So, it’s not like we should be pining for those days.… I think it’s really important to remember that nothing is a given and things change always. There is never a normal.”
Sheff’s eager embrace of profundity is what has helped sustain Okkervil River — named after a short story written by Tatyana Tolstaya that takes place on the eponymous body of water — since the band was founded in 1998.
Originally formed in Austin, Texas with two of Sheff’s high school friends from New Hampshire, Okkervil River has evolved and mutated over the years, with Sheff being the one constant. He has shifted the band’s sounds from traditional folk to noirish synth pop to sun-dappled, 70s radio rock, defying convention with each new album.
For this tour, Sheff is playing Okkervil River songs solo, and while that’s mainly to cut down the health risks from traveling with a cohort of musicians, it has him pondering the state of his band.
“It’s this slightly odd thing that I’m the only original member and I do conceive of it as a band, but there has never been the same lineup — it’s not like Tom Petty and the Heartbreakers,” said Sheff. “I mean, I’d probably need an hour’s worth of therapy to really delve into the meaning of what Okkervil River is as an entity versus what I am as an artist.”
Sheff had plenty of time to ruminate on this issue during the pandemic, a time off he said he found strangely liberating. Without the pressure to tour or to attend to other working musician duties, Sheff was able to focus on creating art.
“I enjoyed having that boot off my neck. In this line of work, it can feel like you’re constantly being kicked in the ass by a million little feet. ”
Sheff said he’s not sure yet how to package the batch of songs he wrote during the pandemic, though he’ll be making decisions about that soon. In the past year, he did release two songs — the sprawling, oddly topical ballad “In a Light” and the jaunty foot-stomper “It Hasn’t Happened Yet” — that were originally composed during the sessions for 2018’s “In the Rainbow Rain,” the last Okkervil River album of new material.
During the pandemic, Sheff also issued “A Dream in the Dark,” a four-record live retrospective, collecting material from nearly 15 years of performances. The live album was a fitting reminder of Okkervil River’s legacy of adaptation and evolution as well as Sheff’s quest to find sense in the margins of life. He said it was unnerving yet illuminating to review the trove of recorded Okkervil River material.
“It’s funny to look at the different versions of yourself,” said Sheff. “Like, ‘Look at that guy, he thought he was so cool.’ And I clearly wasn’t. Then there are other versions of myself that I remember as cringey but didn’t turn out to be too bad.”
Few artists are able to speak of themselves with so much candor and self-effacement. Perhaps that is because Sheff is as philosophical about life as he is about death. Last year, his longtime bandmate Travis Nelsen passed away unexpectedly.
“I loved Travis like a brother,” said Sheff. “We really went through a lot of ups and downs, but he was such a special person. I think about him every day.”
As a musician who puts himself out nakedly to the world with each new endeavor, Sheff is well positioned to capture the grief that occurs when a dear friend dies. He understands that there is power in words — a power to heal and unite.
“Probably the most human thing I can think of is to tell stories,” said Sheff. “Yeah — some stories can start wars and get you killed. But they also have the ability to change the world for the better. I truly believe that.”
IF YOU GO Okkervil River with Damien Jurado
Where: Starline Social Club, 2236 Martin Luther King Jr. Way
When: 7:30 p.m., Friday, December 3 Tickets: Sold Out
Contact: (510) 350-7656, www.starlinesocialclub.com
Where: Henry Miller Library, 48603 CA-1, Big Sur
When: 3:30 p.m. and 7:30 p.m., Saturday, December 4
Tickets: Sold Out
Contact: (831) 667-2574 www.henrymiller.org
Where: Sebastiani Theatre, 476 1st St East, Sonoma
When: 8 p.m., Sunday, December 5
Contact: (707) 996-9756 www.sebastianitheatre.com