Review: Dar Williams, City Winery, Chicago
Lots of shows, gigantic or intimate, can collapse or sail into your happy memories based on the venue. Taylor Swift sure did her best to fill giant sports stadiums, with mixed results. On the much smaller scale of live music, I recently saw singer-songwriter Dar Williams at Chicago’s City Winery. 300, seated, as opposed to 50,000+, detached. Different shows completely, apples and really great oranges, one bitten into in the midst of a crazy glowband army of teens and gay best friends, one a tasty Valencia peeled as patrons push away plates and debate dessert.
Both can be great, and proof of that is, Dar Williams, not a laser in sight, once again didn’t disappoint. I am unabashedly a fan and have gone out of my way, once braving an epic hangover, to see her perform live, many times on many sizes of stage, so before you think I’d ever boilerplate this review – take my possible bias and stick it, sorry, stack it, against all of the mentally banked great shows to which I can compare this somewhat unique night. And, as a inadvertent test, I had with me this time an unwitting “control group”, a Dar newbie, who likes this genre, and is very into small-scale live music, as she is married to a musician. I mayyyy have inadvertently upped the stakes by going on and on, preshow, about how wonderful this first-experience would be, how welcoming, how entertaining Dar is in her interaction with her fans (um, now that I think of it, during a pre-show drink or three the phrase “music that is potentially life-changing” might have been uttered.) No good scientist would bias a control group like that, but, whoops, I veered from protocol, and we both went in to the show at City Winery with lofty expectations.
And we left happy. In good voice and good mood, Dar Williams delivered to a capacity crowd. Though not touring to plug an album, she did do a new composition in her set, about an hour into the show, a fantastic piece called “Time” (I think). It was thoughtful and smart and catchy, as is most of the songs she dips into for live shows. The rest of the evening consisted of compositions gently curated from now 25 years of records, opening with “Emerald” from the album of the same name, 
and including very personal compositions like “Blue Light of the Flame” and “After All”. There are no proper “hits” to hit – she is not the kind of artist that has stormed the radio charts, frustratingly– but this fanbase is loyal and thorough in their knowledge, so each might have an opinion about what is the “Born to Run” of her catalogue. The sing-along tunes “The Babysitter’s Here” and “Iowa” were welcomed with enthusiasm – instead of Bruce shouting to the crowd about the dream of the highway, we had Dar invoking wistful smiles, nostalgia and peace signs.
Dar Williams: smart music and human stories
As she did with “Babysitter”, Dar starts most songs with an intro about its source, or sometimes, her current state of mind in choosing it for that night’s performance. Onstage, as a petite figure with a large guitar seemingly in need of constant tuning, she is genuinely funny, possibly more funny than she even realizes. Candid and current, or apologetic if she is reminiscing a bit, about to sing a song that is showing its years, she invites you, old or new fan, into the heart of songs that can sometimes be lyrically overpacked, but almost always a delight, like the rewarding rummaging that goes on in the large handbag your favorite aunt digs into when she remembers she “brought you something”.
Insider info: never, in my years of seeing her live, is her stage chat repeated, canned, or trite. Even as a new fan, like my delighted companion, you have all you need to sit back and enjoy.
In Europe she tends to be solo, just a girl and her guitar. At the City Winery show, she was accompanied by the fantastic Julie Wolf . This might have contributed to the tenor of the evening. While I must note that there seemed to be mixing issues between guitar, piano, and Julie’s beautiful, occasional, back up vocals – and indeed, Julie did frequently gesture towards the figure in the back running the board. These running musical calibrations, and the obvious long term friendship and looseness between the two, plus possibly the circumstance of it being long-time opener Lucy Wainwright Roche’s last night with the two, combined to deliver a show that was delightful in its imperfections. We confirmed our opinions about the sound level issues with fellow, happy and chatty, concert-goers while waiting outside for a taxi.
City Winery
This led me to wonder about City Winery 
as a venue. As this is a national chain, you might be familiar with their various locations. The Chicago location was, truly, lovely. We, both Chicago natives but unfamiliar with the neighborhood, thought it might have been a new build, but turns out this multi-purpose space is an award-winning reclamation of a former refrigeration warehouse, built in 1911. City Winery here is leaning into a Napa vineyard/exposed brick groove, with a dinner layout of long shared tables but with your date on your side, not across from you. While not a dealbreaker for music, I couldnt help but start to think of which acts would work in this slightly lofty and pristinely kept, 300- seater dining hall. Prior to the evening’s acts, rotating screens promoted upcoming shows (and good stuff is on the calendar, you should check it out)
But thinking of sitting, chair-grooving, gesturing to a server for a latte while watching Los Lobos seemed either an odd fit, or scary proof that Los Lobos fans are aging rapidly.
Or, maybe as Dar might sing, they are “Aging Well” (fans, I’ll pause for chuckles…) I for one prefer seeing the deceptively rousing – she’ll get you going, this one – Ms. Williams in a place where I can get up and bounce and cheerfully sing along and feel the buzz of the crowd. But hey, I also enjoyed sitting, sipping my delicious wine (City Winery knows what they are doing with the wine list, it’s right there in the name for God’s sake), and the show was as wonderful as I expected.
Let’s get a second opinion
But I’m talking from a long time fan perspective. I need to leave you with this note from my first-timer pal whom I asked for a few review notes.
A second opinion on Dar Williams
Martina, thanks for a great show! After prelistening to a few [Dar] songs you recommended, I was ready for a chilled, Lilith Fair and somewhat “worthy” night, maybe a big dose of current politics? I had so much fun, her intros were great for this newbie, and yes, you hinted at how entertaining she is, but yes, really funny and smart. The songs I didn’t preview were as enjoyable as the ones I dipped into – though knowing her lyrics in advance sure helps! Masters in English? Two thumbs up!!
I couldn’t say it better – see Dar Williams on the current tour, with Julie Wolf preferably, or when she collects a new album’s worth of songs and heads out again.
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A former ABC National, Dallas and Atlanta radio personality, Martina O'Boyle is now making movies and covering culture in London, Dublin, and as far in Europe as the cheapie flights will take her, for Pop Culture Beast.