Jeff Tweedy’s latest monumental work, ‘Twilight Override’—a triple album featuring 30 songs across three discs—began its life on a simple road trip. The idea sparked during a four-hour drive with his sons, Spencer and Sammy, when Tweedy, the leader of the esteemed band Wilco, decided to listen through The Clash’s 1980 triple album, ‘Sandinista!’ The sprawling, genre-bending nature of that record ignited a similar ambition within him, leading to what he jokingly refers to as ‘Sad-inista.’
Tweedy acknowledges that creating a triple album is somewhat ‘counterintuitive’ in today’s fast-paced, surface-level culture. Yet, he sees it as a rewarding experience for a certain type of listener, offering an extensive musical landscape to truly ‘luxuriate in.’ He aimed to create an album designed to command two hours of intentional listening, a challenge he embraced both for his audience and himself.
Originally conceived with working titles like ‘Triple Rainbow’ and ‘Tons of Time,’ ‘Twilight Override’ reflects Tweedy’s commitment to artistic exploration. He believes there’s value in allowing songs to coexist that might not make the cut on a more concise, ‘maximum impact’ album. This approach facilitates a deeper engagement, rewarding those who are willing to commit to the journey.

From the comfort of Wilco’s Chicago studio, The Loft—a space brimming with guitars, keyboards, and musical devices—Tweedy, at 58, discussed his philosophy. His touring band, which includes his sons Spencer (29, on drums) and Sammy (25, on vocals and synthesizers), often rehearses here. Behind him in the interview was a familiar sight for fans: a doll of Devo’s Booji Boy mascot and a painting of the longhaired white cat that graced the cover of Wilco’s 2015 album, ‘Star Wars.’
Tweedy’s prolific songwriting career dates back to the late 1980s with Uncle Tupelo. After their split in 1994, he formed Wilco, a band whose lineup solidified in 2005. Over the decades, Wilco’s sound has evolved, blending country, punk, folk, psychedelia, and electronics. As he penned in his 2018 memoir, ‘Let’s Go (So We Can Get Back),’ his life’s calling was to ‘gut myself in front of strangers, letting all the raw emotions come flooding out, making a fool of myself with my own words.’

Wilco has become a self-sufficient indie-rock institution, owning its studio and label, dBpm. Since 2010, they’ve hosted the biennial Solid Sound festival, bringing together diverse musical acts at the Massachusetts Museum of Contemporary Art. Despite early financial losses, Tweedy maintained the festival, driven by the belief that it was simply ‘worth doing.’
This pursuit of sustainability has been a ‘lifelong project’ for Tweedy, guiding every decision. He emphasizes a disciplined approach to songwriting, encouraging daily practice—even if it’s just 20 minutes devoted to writing a ‘bad’ song, because, as he says, ‘you’d end up writing a good song every once in a while.’
When not with Wilco, Tweedy channels his creative energy into solo albums, with ‘Twilight Override’ marking his fifth. He tours with a band featuring his sons, Spencer and Sammy, a dynamic that profoundly influences his sound.

The album is divided into three sections loosely exploring concepts of past, present, and future, with fluid boundaries between them. ‘Twilight Override’ earns its extended runtime without feeling padded; only three songs exceed five minutes. The arrangements are intimate and organic, often centering on Tweedy’s acoustic guitar, enriched by Macie Stewart’s violin, echoing the warmth of artists like Elliott Smith and Nick Drake, or the folk-rock sensibilities of Simon & Garfunkel and early Bob Dylan.
Yet, subtle dissonances and unexpected electric guitar solos occasionally pierce the cozy atmosphere. Many tracks, especially the enigmatic ‘Blank Baby,’ feature lush vocal harmonies from his touring band, including James Elkington (guitar), Liam Kazar (bass), and Sima Cunningham (keyboard), who will join him on tour this October.
The songs on ‘Twilight Override’ are tapestries of memories, aspirations, and reflections on life, love, and the relentless passage of time. ‘Forever Never Ends’ vividly recounts a high-school dance night, concluding with his car breaking down, leaving him ‘on the side of the road in a tuxedo.’ ‘Mirror’ delves into paradoxes of existence, pondering mortality and rebirth: ‘Your mind goes blind and you are erased / You will be the person taking your place.’

Mortality has long been a constant theme in Tweedy’s lyrics, an inevitable outcome of loving people and experiencing loss. He observes the world’s pain, from personal bereavements to global tragedies, acknowledging the ‘horrific information coming in instantaneously.’ Yet, ‘Twilight Override’ is ultimately a defiance of darkness through abundance.
Tweedy concludes that despite our struggles, we are driven to ‘keep moving, keep putting one foot in front of the other and wanting to be here.’ The album’s underlying message, he says, is like an old joke about a restaurant with terrible food but tiny portions: ‘The world’s kind of painful — but God, I can’t get enough of it. I just don’t want it to end.’