Recording Academy P&E Wing and Songwriters & Composers Wing get "Up Close and Personal" with Wilco's Yankee Hotel Foxtrot

Cheryl Pawelski (left) and Jeff Tweedy (right) sit down for the event "Up Close and Personal with Jeff Tweedy and Cheryl Pawelski," presented by the Recording Academy® Producers & Engineers Wing®, in collaboration with the Songwriters & Composers Wing, held on Feb. 27, 2024, at the Rhapsody Theater in Chicago, IL. (Photo Credit: Daniel Boczarski)

The Recording Academy® Producers & Engineers Wing®, in collaboration with the Songwriters & Composers Wing™, recently presented "Up Close and Personal with Jeff Tweedy and Cheryl Pawelski" (archived video here), as part of the Recording Academy's series that aims to provide rich insights into the relationship between songwriters and producers. This latest event, hosted by the Recording Academy’s Chicago Chapter at the Rhapsody Theater, took place on Feb. 27, 2024, and featured an unforgettable conversation on craft and creative process with two Midwest industry icons examining the 20th anniversary re-release of Wilco's seminal Yankee Hotel Foxtrot, which won a GRAMMY® in 2023 for Best Historical Album.

Tweedy is a four-time GRAMMY-winning American musician, songwriter, author, and record producer best known as the singer and guitarist of the band Wilco. He has released 20 studio albums during his storied career, including 12 with Wilco. Pawelski, who produced and curated Yankee Hotel Foxtrot (20th Anniversary Super Deluxe Edition), is also a four-time GRAMMY-winner and has worked on archival projects by everyone from the Beach Boys to Big Star to Willie Nelson across her career.

Held in front of a live audience, emceed in the theater by Chicagoan family music artist Justin Roberts, and simulcast to audiences in three different Midwest recording studios, this session provided an unprecedented look into the making of the original album and the challenges and strategic decisions necessary to pull together a project of such significance. From the original songwriting and revisions, to selection of tracks for the 20th anniversary edition boxed set – including dozens of alternate takes, remastered tracks, live versions, interview content, and more – Tweedy and Pawelski shared an intimate look into the forces at play.

"I think music in general is a safe place to fail," Tweedy shared. "When you take your ego out of it and you look at it as a daily practice of spending time with yourself in your imagination… once you do it for a long time, it really makes the notion of failure almost quaint." He went on to say, "There are a lot of things on the boxed set where I would listen to them now and go, 'That was good enough.' But it wasn't satisfying… Rock and roll was built on that thing, above all else… be yourself, without any apology, and on purpose." Tweedy continues, "Nothing's really ever lost. You learn something about yourself writing terrible songs. I know myself better because of the songs that you've never heard."

Pawelski, who often specializes in historical releases, reissues and previously unissued vintage recordings, utilized her skills as curator and producer to add the extra touch that brought the entire project together as a cohesive unit. She went on to elucidate her rich legacy in the music business and how experiences helped her tackle the foreboding process of digging through the sessions' flotsam and jetsam. "The world kind of changed during the making of this," Pawelski said. "The band certainly changed, and also, technology changed," she explained. "So, we had everything — we had DATs, we had ADATs, we had tape, we had cassettes, we had CD-Rs." Regarding her process of taking on such a massive undertaking, Pawelski states, "I go backwards and try to reconstruct how things happen, and it's always incomplete and I don't know what I'm missing, so it's extra fun. But this particular record was done and undone in a lot of ways… some of the latter recordings sound like they're earlier recordings." She notes that the prospect of stewarding Yankee Hotel Foxtrot was "kind of terrifying" because of how meaningful the record is. "It really was a Rubik's cube. I would get the orange side done and I'd turn it over."

Tweedy also took time to discuss the magic of collaboration. "I've gotten really good at being alone with people. So, I think that facilitates collaboration to some degree," he said. "What I mean is being as forgiving of myself with other people in the room as I am with myself alone." This mutual respect and insight serves as a watermark to the success of this evocative album and its 20-plus-year legacy.

Yankee Hotel Foxtrot (20th Anniversary Super Deluxe Edition) is available on vinyl and CD, as well as on major streaming services.