Review: Jess Williamson Offers Up a Dazzling Country Spectacle at Judson & Moore

What was supposed to be a small, intimate country show under the heavenly starry lights of the Hideout turned into an electric, whiskey-drinking Thursday evening at Judson & Moore Distillery that oddly felt even more intimate considering both the presumably smaller occupancy of Judson & Moore and the fact that the venue change was rather last minute. Jess Williamson started her 2023 American tour a couple of weeks before the release date of her new album, Time Ain’t Accidental, so she could get the opportunity to surprise her fans with performances of all the songs she’d been working so hard on for the past several years and even though I do prefer sitting with a new album for a week or two before seeing the artist live, there’s certainly something to be said about the excitement and devil-may-care attitude that comes with hearing an artist you love treat you to so much new music that you haven’t had the chance to dive into yet. What was even more of a treat was Jess’ decision to have Chicago’s newest folk queen, Kara Jackson, open for her in a shining performance that so perfectly set the stage for her second night of two in Chicago.

Some of the most memorable concert experiences I’ve had in Chicago so far have frequently been for artists who grace the stage with nothing more than their voice and guitar. There’s something so special and awe-inspiring about seeing someone all alone on a stage commanding hundreds of people all at once with nothing but the music of their heart. Kara Jackson was certainly no exception to the rule as her performance Thursday night was as moving as they come. Having just released her spellbinding debut album, Why Does the Earth Give Us People to Love?, her setlist mostly contained songs from that album as well as a couple from her 2019 EP, A Song for Every Chamber of the Heart. To start off her set, she opened with a cover of “Right Wrong or Ready” by ’60s folk artist, Karen Dalton, which was so in her wheel-house of songwriting that if she didn’t say it was a cover, I would have just thought it was an unreleased track for her latest album.

Since the production of her new album is as sparse, spontaneous, and pure as an iPhone voice memo (and I mean that in the best of ways), it wasn’t very hard for her to sound even better live. Songs like “no fun”, “therapy”, and “pawn shop” all hit me much harder live perhaps because of the emotional weight of seeing Kara perform these songs mere feet away from me but I mustn’t discount just how beautiful and powerful her already incredible singing voice sounds in the flesh. She then went on to play what she believes to be, contrary to Pitchfork’s beliefs, her one and only love song on the record entitled “brain.” The song itself wasn’t one that initially stood out to me on her debut but that certainly wasn’t the case hearing it live as it seemingly took on a completely different persona altogether that really made me reconsider its place on the record. She ended her set with the generous one-two punch of “dickhead blues” from her latest album and “Ray” from her 2019 EP. Why Does the Earth Give Us People to Love? will undoubtedly go down as one of the finest folk records of not only this year but of recent memory, so if you ever have the chance to hear Kara perform her songs live, I highly suggest you make the trip. My only disappointment was that she had no merch for sale. Maybe next time…

It wasn’t long before Jess Williamson and her scrappy band of rebels took the stage and went into “As the Birds Are” from her 2020 album, Sorceress. Any time you write a song with a drum intro, it really is best to just open all your shows with that as it sets you up pretty well for success. Being a week away from the drop of her new album, Time Ain’t Accidental, Jess delivered the goods by not only playing a number of new songs outside her three previously released singles but also gave us the honor of being the first stop on her tour that was privileged enough to buy her new album early! Even though we knew her set was going to be mostly new songs going in, she still gave us a little bit of the old early on in the night with “Pictures of Flowers”, her gorgeous 2020 collaboration with Hand Habits that resulted in just about the most precious indie folk song you ever heard.

Digging into her new album now, she played several unreleased cuts in a row starting with the energetic and rebellious “Topanga Two Step.” Next was probably my favorite of her new songs called “God in Everything”, a song backed with an upbeat rhythm section and beautiful alt-country melodies that just made my lil heart soar. She slowed it way down with “Tobacco Two Step”, a modest country ballad filled with majestic guitar leads and her patented twangy voice tinted with just a hint more sadness than usual. Getting back to the fun, upbeat side of her musicality, Jess invited Kara Jackson back on stage for a boisterous duet of the John Prine classic, “Angel of Montgomery.” Their performance sent me on a nostalgia-fueled train ride back to my childhood when Prine was basically a daily vitamin in my house and it truly made for the highlight of the night for me. Jess then set the guitar aside for the title track to her new album, “Time Ain’t Accidental”, an uproarious love song about all the unexpected twists and turns life gives you that almost make it seem accidental when you find that special someone when it was really fate all along.

The first time I saw Jess Williamson perform live was when she was in town with Katie Crutchfield of Waxahatchee fame performing under the moniker Plains and playing songs from their new album, I Walked with You a Ways, one of my absolute favorite releases of 2022. Jess, being the gracious performer she is, decided it was high time for some Plains songs and gave us a wonderful performance of a song she wrote for the project called “Abilene.” It was so nice to be reminded of such a great album with such a fantastic performance and it’s never not a pleasure to belt out those climatic lyrics, “Texas in my rearview, plains in my heart” with an audience who gets it. Before exiting the stage in preparation for her encore, she closed out with “Hunter”, the first single for her new album and a song that she first debuted while on tour with Plains last year. I loved it the second I heard it live with Plains and I loved it even more hearing it a second time with her own band; the song is already a bonafide classic as far as I’m concerned and it’s all uphill from here.

For her encore, Jess brought us back again to Plains with the title track to the album, “I Walked with You a Ways.” The song may not be my go-to song from the album but it’s definitely the song that means the most to me so I was positively ecstatic getting to hear it live for a second time. She played the song at about half speed so all the emotions already flowing through the song felt that much more amplified and in your face. About halfway through the song, her band came back and added some much-appreciated texture to drive the song home. Saving the best for last, Jess capped the night with “Wind on Tin”, her most well-known song taken from her 2020 album Sorceress. The song itself is so dark and dusky that you couldn’t have asked for a better song to both close out your night and get you ready for bed.

All photos by Julian Ramirez

Lorenzo Zenitsky
Lorenzo Zenitsky

Lorenzo Zenitsky is a Chicago-based software engineer, amateur bedroom metal musician, and a semi-frequent drinker of coffee but only if it's iced. If he's not admiring his terrible Simpsons tattoos in a gently cracked mirror, he's usually at a local show vibing to great tunes and abhorrently priced beer. $15?! Get outta here...