Jeremy Messersmith took the stage of the Parkway Theater on the evening of Saturday, Oct. 28 as part of a weekend of Halloween shows. With a performance led by humor and storytelling, the nine-piece ensemble brought the audience on a Halloween journey.

He arrived to an audience of dedicated fans donning costumes of all sorts, including The Shining twins and Margot Tennenbaum. Though he nor his bandmates were in specific costumes, their all-black garments contributed to the gothic cohesion of the night.

The Parkway’s stage was decorated with cobwebs and graves possibly summoned from Spirit Halloween. According to Messersmith, the Halloween show has been a tradition for more than 10 years — and they seem to have it down.

It’s easy to forget that Messersmith is not originally from Minnesota. He has long been a favorite in the Twin Cities indie scene, consistently releasing music since 2006, when he debuted The Alcatraz Kid. He has since embarked upon a series of melancholic, witty folk and pop projects that have continued to bolster his local and national notoriety.

He started his performance with a quick “Happy Halloween” before embarking on some of the more upbeat music in his repertoire. Perhaps just as stunning as Messersmith’s vocal performance was the unity and musical performance from his bandmates and the powerhouse Laurels String Quartet.

Throughout the show, it felt like each instrument and musician had their moment to shine, but they also came together in a powerful unity to deliver a mesmerizing and joyous sound. His songs have gorgeous guitar and bass lines, which paired incredibly with the quartet.

He also brought on saxophone player and singer Lucy Michelle twice throughout the show. The show, originally billed as “Jeremy Messersmith & Friends” became, in his own words “Jeremy Messersmith & Friend” as other surprise musical guests dropped out last minute due to Covid. Still, the night felt abundant, especially considering the scale of his band and the intrigue of his music.

Throughout the show, Messersmith created a sense of community with the audience and built a humorous rapport that made a series of covers and unorthodox performances more fun. He told musical ghost stories and chose deliberate covers while delivering brief lines of comedy between songs. Early on, they covered “Bad Blood” by Taylor Swift. Though chosen likely for the spooky nature of the revenge story, the choice felt like an homage to Taylor Swift’s recent re-recording of 1989.

The night slowly descended into a more hellish venture following a brief intermission. Unlike most concerts, the intermission gave the audience a break to talk about the set, check out each others’ costumes and build excitement for the second act.

The nature of Messersmith’s work is story-oriented. With each of his songs, he weaves stories about characters and takes listeners on sonic journeys via his lyricism. He does this with a slightly sarcastic, but ultimately inviting sense of humor. His latest album Late Stage Capitalism, which came out in 2018, pokes fun at our strange modern times but ultimately delivers comfort.

The second act started off with a bang, featuring some of Messersmith’s more upbeat songs. He invited us on a journey to the underworld, sorting through his extensive catalog to find the spookiest numbers. Messersmith joked that it was “just a visit” to hell as he entered into a cover of “Stairway to Heaven,” an 18-minute-long sonic journey. But just seconds into the familiar and intricate guitar playing, he was interrupted by a demonic message, requesting Messersmith’s latest single “666,” a creepy and plucky tune that the audience thoroughly loved. He made sure to thank the sound and visuals people on his team for creating such an immersive experience.

Most of the songs from the performance were pulled from his 2010 album, The Reluctant Graveyard, with definite throughlines to his most recent single, “666,” the project has spooky-yet-light undertones. The entire album explores themes of life, death, love, and loss, through deliberate lyricism and at times, eerie sonic choices. It was a reliable catalog to pull from throughout the evening.

As the set continued through the hell portion, Messersmith gave his most impressive vocal performance of the night with a cover of “Highway to Hell.” He captured the energy of AC/DC with aplomb, delivering vocal acuity that was sincerely awe-striking.

In high contrast to AC/DC, his performances during the evening from his 2017 album, 11 Obscenely Optimistic Songs for Ukulele, tapped into his tenderness as an artist. This work seemed pulled from a children’s book at times — and his show was no real exception to that. It was a PG Halloween spectacle, and despite a brief visit to hell and a solid sense of humor, the show at times felt like show and tell.

This isn’t necessarily out of character, according to the 12-year-old daughter of bassist Ian Allison, Messersmith is great with kids. Growing up with the band (the drummer was her babysitter) she’s always been involved in the band. She recalled the band’s sense of unity and the excitement around the Halloween shows as a kid in the music scene. Despite her clearly being one of the youngest people there, the show placated to a sense of youthful exuberance or the inner Halloween-obsessed child that lives within us all.

The show eventually ascended from its hellish venture and landed at a more optimistic place. He closed out the show with a solo ukulele encore of “Everybody Gets a Kitten.” He claimed, before starting in on the song, that it was a spell. A sort of hex for world peace, he took the audience through his final song, requesting that they sing along. The concert ended with a crowd singing in unison and a standing ovation. The crowd filtered out happily in costume, excited to be part of a Halloween tradition led by a great local band.

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Set 1
Lazy Bones
Dillinger Eyes
Organ Donor
Halloween Store 
They're Coming to Get You, Barbara
Spooky (ft. Lucy Michelle)
Halloween Song 
Everything is Magical
John the Determinist
What's He Building? (Tom Waits) 
Ghost
Bad Blood (Taylor Swift)

Set 2
Violet!
Sukie in the Graveyard (Belle & Sebastian) 
I Put a Spell on You (ft. Lucy Michelle)
Song for the Dead
A Girl, A Boy, and a Graveyard
Stairway to Heaven/The Devil vs jeremy messersmith (Led Zeppelin)
666

Devil’s Haircut (Beck)
Hell (Squirrel Nut Zippers)

Highway to Hell (AC/DC)
Deathbed Salesman
Do You Realize?! (The Flaming Lips)

Encore
Everybody Gets a Kitten