Zowie started performing in clubs in 1999. He played solo punk rock shows at The Brownestone and Lightpainter Gallery around this time and dyed his hair blue. He headed downtown after that playing on acoustic at Café Kaldi from 2000 to 2002 where he met Merlin. Zowie formed a folk rock band with Merlin called Cult of Fiction which played all around town at Café Kaldi, the Ramada Inn, Good Times, and The Entersection. They also played a few shows in Grand Rapids, Michigan during Zowie’s computer networking internship. At The Morning Star 76 Café open mics and a couple shows at The Liquid Room. The band broke up. In 2007 Zowie played a gig with Charles Canterbury at Scalleywags improvising and was recording several post punk LPs on his computer from 1999 to 2009 which have now been released under the name Dark Jester. During this time in 2007 Zowie tried to form a Garage Rock band called Foursquare which didn’t really work out.

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In 2010 Zowie hit the open mic at The Box Social where he ran into Crow and Wembley. They soon decided to form a Flower Punk band called The Freejacks (The band name was based on the movie Freejack) and performed at The Shamrock several times, The Cock n Bull, Growlers twice, The Closet, and The Blue Owl. They recorded an album called Escape on Zowie’s computer and a Live album. They took a break at the end of 2011. Zowie worked on his casiopop project called Star Mice and recorded 4 LPs which he released all at once in 2014. Zowie performed solo at The Tea House open mics for a few years.

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In 2017 The Freejacks did a reunion show at The Shamrock and a house party. Zowie also performed a few open mics at The Cock n Bull and Munchies around this time. The Freejacks started recording demos with Joe Reynolds and sending out material to radio stations. They recorded Shadows of the Limelite in 2017, Embers in 2020 which received a lot of recognition on Spotify, and Dark Matter in 2021. Becoming mostly a studio band they made it to underground radio stations in France, Germany, UK, Ireland, Belgium, and USA. In 2021 they were invited to present a single on Indie Network Radio and reached an audience of several hundred million so they are told with the single Pink Haired Punk Rock Princess. The Dark Matter album cover was shown on Tzik TV as well as the song Pink Haired Punk Rock Princess. Zowie performed an open mic at Big Top Brewery, his first live performance in years. Then The Freejacks reached #10 on the Indie Top Chart for 13 days, stayed in the top 20 for six months and stayed in the top 30 for 10 months. The top 30 is being played on 800 underground radio stations a week around the world and being shown on a TV station somewhere they are told.

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The Freejacks recorded the single Stop the Deforestation in 2022. It was aired only on Herbal Remedy Radio at first and is currently being played on Ze Music Television. Zowie played a few open mics in the Gulf Gate area. The Freejacks played a Hootinanny full show on Labor Day weekend and reunited with Crow after the show who had left the band during the Embers EP in 2020.

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Zowie also does solo work in his side project Dark Jester because the members of The Freejacks don’t really have enough time to work on all of Zowie’s songs. Dark Jester has also been on a few radio stations. Dark Jester released a new LP called Blacklight in 2020 and another one called Sore All Over in 2021. Zowie's acoustic project Zowie Demmon can be found on Spotify. That is what he is doing while his band The Freejacks are on break while Wembley is in school in Ohio.

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On December 13, 2023 Zowie changed his stage name to Zowie Demmon Canterbury.

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You can find all of The Freejacks, Dark Jester and Star Mice albums on Spotify. You can also stream The Freejacks material for free at Bandcamp.