As a young designer who was really into music, designing album covers was always something I really wanted to do. I had always admired the surrealistic work of Storm Thorgerson for Pink Floyd or the moodiness of Vaughn Oliver’s work for 4AD. I had fun in art school designing mixtape covers, but that was the closest I’d ever gotten to creating cover art.
Fast-forward to 2001 when Wilco released their now-classic album, Yankee Hotel Foxtrot. You know the cover, a mostly empty beige square with twin scalloped-sided towers rising from the bottom in black and white. That photo by Sam Jones of the Marina City apartment buildings in Chicago—the band’s hometown—combined with the lyrics from “Ashes of American Flags” indelibly captured the mood of America still reeling from the 9/11 attacks that happened two weeks prior. The band nor the album cover designer could have anticipated the coincidence.
Through twists and turns, the release of the album was digital at first. Wilco’s label rejected the album so the band left the label, negotiated to get the rights, and released the album themselves. They streamed it first on their website before being signed onto another label and having a retail release the following spring.
When I got the album, I pored through the credits and spotted the name of the designer: Lawrence Azerrad. I was pleasantly surprised and shared it with my colleagues at the time, for Azerrad, like me and most of my designer friends, was an alumnus of California College of the Arts. He was in my graphic design class.
Azerrad and I reconnected years later. For a design conference in Chicago that I was co-producing, we held a session at Wilco’s Loft, their home base and studio. Certainly one of my dreams come true!
What surprises me and what I admire about Azerrad and his work with Jeff Tweedy and Wilco specifically, is how much it’s not about him. I remember him telling me about sessions where he’d just set up his computer as the band was rehearsing or recording, and they’d jam while he designed. Tweedy would come in, give some feedback, and they’d jam on the design together. Rinse and repeat. The way Azerrad designs these covers, it’s more like he’s channeling the artist’s creative energy, and their collaboration is the output.
Rachel Cabitt recently interviewed Azerrad for the 25th anniversary of the album’s release. He says:
…as our connection to culture becomes more digitized, as AI plays a bigger role in our lives, and as discovering music and art through our phones gets almost effortless, it’s on creatives to find new ways to stretch toward deeper connection, to provoke more awe and wonder, not less. Because art, in all its forms, can get us to think more deeply about who we are, what we’re doing with our time here, and what we want to leave behind.
Right on.

