Will Gillespie's Hallowe'en Spooktacular

Will Gillespie might wish that every day was Hallowe’en. We just caught up this passed summer with singer and songwriter turned playwright and actor,

Will Gillespie might wish that every day was Hallowe’en. We just caught up this passed summer with singer and songwriter turned playwright and actor, Will Gillespie, for his latest theatrical production Diamond in the Rough. While the light–hearted play about Neil Diamond coming to Hamilton’s stages won Audience Choice Award at the Hamilton Fringe Festival, Gillespie is bringing the same cast together to revisit his first play Swingin’ In St. John’s next weekend. But before November begins, Gillespie has to celebrate a night that speaks to his soul. 

“We debuted Swinging in St. John’s back in July 2019 at the Hamilton Fringe Festival. We wanted to see if we could do that play with the same cast from Diamond in the Rough.” explains Gillespie. “I really enjoyed working with that company and I knew that they could do justice to the play and this opportunity came up with the arts and cultural council of Burlington. They had this bursary to book the Burlington Performing Arts Center, we applied and got it, so we thought, why not do a weekend?

“I’m currently working on a third play to debut next year and with each one I’m getting more original and personal,” adds Gillespie. “My second play kind of told my own story but through the lens of Neil Diamond playing a dive bar in Hamilton. The next one I’m working on is about a jazz singer from outer space but before we get into that, Swingin’ In St. John’s was like an Elvis movie set in Newfoundland and we’re bringing that back for a couple of shows in Burlington.”

You can catch two performances of Swingin’ In St. John’s at the Burlington Performing Arts Centre on Saturday November 2 at 7:30 pm and Sunday November 3 at 2:30 pm. But while he’s still getting traction from his catalog of plays he also remains a singer and songwriter that performs on our local stages — and Gillespie hopes to do more of that.

“I’m inspired lately and plan to get back into that.” says Gillespie. “We were on a road trip recently and I find fall generally inspiring. Coming from a folk rock background, that music is sort of the soundtrack to Fall so listening to that and going back home reconnecting with my roots sort of brings me back — writing songs and performing are the main crux of what I do, whether it’s plays or just me with a guitar on stage. It’s coming up with songs and connecting to an audience. I’m hoping after the next big musical, to release a record that’s just Will and some songs and switch to a one man show for a while.”

For Hallowe’en though, Gillespie is not playing solo as he’s cobbled together a band for a seasonal party that combines his quirky and theatrical inclinations. Will “Count Rockula” Gillespie and his Haunted House Band — featuring Chris Crackin-Hell (Cracknell) on accordion and Theramin, Dave Ghoul (Gould) on drums and ‘Hairy’ Harry White on bass — will be playing some spooky rock and roll.

“I’ve been wanting to get this kind of show together for a couple of years now,” says Gillespie. “I'm a cheesy guy that likes campy things and puns and Hallowe’en is the one time of year that the general population can get into that and actually encourage it. They can cut loose, have fun and allow themselves to be a little cheesy, kooky and spooky. It’s when if I say ‘Boys and ghouls’ instead of a groan, I get a maniacal laugh. 

“We’ll be playing some classic ’60s rock and roll tunes mixed in with some of the darker side of my own oeuvre as well as the “Monster Mash” and things like that,” adds Gillespie. “DJ ‘Scarelie Wild’ will be spinning vintage vinyl to shake your boo–tay and Dave Ghould will open the show performing eerie instrumentals. Susan Robinson will be projecting classic monster movies in black and white and giving out prizes for best costume and best howl or maniacal laugh. The usual classic Hallowe’en stuff. Hallowe’en and New Year’s are the two holidays I especially like to play because with New Year’s is the one day outside of a wedding or the opera where people can wear tuxedos and have champagne. Hallowe’en is another time where people can get dressed up and have fun, be silly but also listen to great classic rock and roll. there are more people like me — at least on that night.”

Will Gillespie's Hallowe'en Spooktacular happens Thursday October 31 at This Ain't Hollywood. The doors open at 9pm and $10 gets you in. Click on

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