A Guide to Drag City in 7 Records

Drag City has been a staple of the Chicago music scene since its inception. The label, which was formed in 1990 by Dan Koretzky and Dan Osborn, has been a home for introspective artists that lets them dive into their craft without pressure. So many Drag City records are a step or two leftward of where they first seem to be, with their nuances and oddities sneaking up on you—you'll listen once, and soon find yourself back there, waiting for them to reveal more. Most of the time you'll find it too.

"We can't take credit for any of the things that these artists have done, but we can take credit for taking a chance on it," says Drag City producer Rian Murphy. "To me, from the very beginning with a band like Royal Trux, we were looking for something that faced against the tide, that had counterintuitive logic working for it, and that was hallucinatory in some way, that ripped you out of what you thought your reality was."

Drag City prides itself on taking a chance on artists, offering them a sense of professional stability while still giving them the space to explore their identities, literally. Will Oldham played under Palace Music, Palace Brothers, and Palace Songs before settling on Bonnie "Prince" Billy. Bill Callahan began performing under his own name after years of using the Smog moniker, and David Berman adopted the name Purple Mountains after the cessation of The Silver Jews.

With each release, the only predictable Drag City mark is a departure from what you typically expect of an artist. In the 1990s, the experimental legend Jim O'Rourke released a series of straightforward records and Joanna Newsom did the opposite with Ys nearly a decade later.

When questioned about any similarities between artists on the label, Murphy strays from traditional genre labels, which have annoyed him for years. Instead, he points to the artists' approach and mentality. "I feel our artists come close to the thing that is for everyone, but their expression, which is a bit more idiosyncratic, is always preferred, by them and us," he says.

Below, we take a look at these idiosyncratic greats with our guide to Drag City in seven records.

Silver Jews

Starlite Walker

David Berman has always had a knack for introductions. With each Silver Jews record, the first few lines out of Berman's mouth would knock you down, pick you up, and push you through the rest of the album. Starlite Walker, The Silver Jews' first record, was the first time many listeners had the pleasure of hearing Berman's bent lyricism: "My friends, don't you know that I never want this minute to end? // And then it ends."

Around the time of the release, many Pavement fans thought the Silver Jews were a side project due to Stephen Malkmus' participation in the band. The band was Berman's show, a podium to grandstand on about the absurdity of the human condition through the use of bone-dry humor, cowboy chords, passenger seat observations, and brutally honest self-reflection.

Starlite Walker laid out some of the tropes and charm that he changed and refined in subsequent releases like The Natural Bridge and American Water.

Palace Music

Viva Last Blues

Over the years, Will Oldham has become one of the figureheads of Drag City. He's released dozens albums under plenty of name changes, none of which feel out-of-character. His third release under the various Palace names is Viva Last Blues, a collection of tracks that straddles the rougher "indie rock" sounds of his earlier work and the backwoods ballads that he would put out after his switch to the Bonnie "Prince" Billy name later in his career.

"Viva Last Blues indicated what Will Oldham was capable of doing," says Murphy. "It felt like there was a potential with Viva that we might be like the Neil Young quote: 'Put me in the middle of the road. Traveling there soon became a bore, so I headed for the ditch.' Viva took us to the ditch. It's difficult to talk about what we were doing in the '90s without mentioning it."

Jim O'Rourke


No release on Drag City embodies its aforementioned "departure from an expected norm" more than Jim O'Rourke's trilogy of records: Bad Timing, Eureka, and Insignificance (all named after Nicholas Roeg films). Throughout the '90s O'Rourke produced records and played in bands such as The Frogs, Gastr Del Sol, and Sonic Youth (which he joined around the time of the discussed trilogy). Then O'Rourke did an about-face and released a set of gentle, acoustic guitar–based songs.

Each record of the trilogy is wonderful in its own right, but the one that found the most historical standing power is Eureka, which landed on several publications' "albums of the decade" lists. On Eureka, O'Rourke shows that throughout all his years of deconstructing musical norms, he learned to appreciate and replicate them as well. He trades droning guitars for simple fingerpicking patterns and screams for his gentle singing voice.

Six Organs of Admittance

School of the Flower

Six Organs of Admittance, the musical project of guitarist Ben Chasny, broke all the rules of folk music. They put droning distortion over acoustic fingerpicking and used sludgy drums when more traditional folk artists might opt for auxiliary percussion. By the time School of the Flower was released in 2003, Organs had already put out 12 records since the turn of the century, each of which had crumpled the definition of folk.

School of the Flower is Chasny at his best. The record drifts between extremes without jarring the listener. Each song is like a dream, effortlessly moving between ideas, not holding onto any concept too tightly, leaving behind a feeling more than actual memories. It's a record of in-betweens, for in-betweens: early autumn, sunset, sunrise, long car rides, waking up, going to sleep.

Joanna Newsom


When Joanna Newsom put out Ys, most of her fans were expecting an entirely different record. The lengthy, dense tracks—filled with swirling verses of arcane references—are a far departure from her previous release, The Milk-Eyed Mender. Newsom's creaky voice narrates personal fairytales over extremely detailed orchestration.

"Everyone had gone nuts over her first record, which had a bunch of lovely short songs," says Murphy. "But then came Ys, which has five songs, is a double album, and all the tracks are close to double digits in length. It felt like that was something we had not seen, but yet, and maybe because of that, keeping within the continuity of Drag City thought."

Bill Callahan

A Shepherd In a Sheepskin Vest

Since he first entered the music world as Smog, Bill Callahan had been releasing records almost every other year—then he became a father. After playing with the idea of giving up music, Callahan regrouped and released A Shepherd in a Sheepskin Vest, his most mature, whittled-down set of songs yet, five years after his previous release.

On Sheepskin, Callahan shows an even deeper appreciation for putting words together. At the beginning of the record, he acknowledges his absence and welcomes the listener back on the track "Shepherd's Welcome": "Well, it's been such a long time / Why don't you come on in? / I kept the old door." And on "Writing," he sums his love of the craft up in a way that doesn't try to be poetic or wise but truthful: "It feels good to be writing again."

Even with the uncharacteristically long time off, Callahan returned as he left—a sage we go to visit who speaks in a way that makes you want to wake up early, smell the coffee, appreciate your loved ones and stop worrying about everything else—with a record that welcomes longtime and new listeners equally.

Purple Mountains

Purple Mountains

After a hiatus from the Silver Jews, David Berman returned in 2019 with a new name and sound. Purple Mountains is arguably Berman's wit at its barest. His lines are witty as ever, but they're sharper and more mature. Sadly, Berman took his own life soon after the record's release. However, his influence has been felt heavily in the months following, with artists from a variety of corners of the creative world praising his one-of-a-kind way of describing the world.

"When David brought us the Purple Mountains record, I honestly felt that this made a fine enough argument to say that the rest of his career had been leading up to this record," says Murphy. "In some ways, I think it's his ultimate record."

Drag City Records