2019 - Audience Choice Award  : Hamilton Fringe Festival "Diamond in the Rough" (original Musical Will wrote )

2019 - Readers Choice Nominee  : "Best Live Theatre" for Chasing Shadows Productions (Will's Company)

2017 - Best of Venue : Hamilton Theatre Incorporated "Swingin' in St. John's" Hamilton Fringe Festival

2016 - Hamilton Music Awards

(Nominee - Contemporary Folk Recording) "Chasing Shadows"

2008 - Sudbury's Musical Playground - Grand Prize Winner (Best Children's Song) : "Swords & Dinosaurs"

2008 - Northern Lights Festival Boreal Meltdown Winner

2008 - Northern Ontario Music Development Program Recipient

2008 - FACTOR Demo Award


I am a Singer-Songwriter, Musician, Actor, Director and Playwright. I live in Hamilton, Ontario. I grew up in a small mining town just outside of Timmins called South Porcupine. I've been a writer since I could hold a pen. Later, I moved to Sudbury, ON where I gained a reputation in that region as a prolific solo Folk singer and troubadour. I was commuting back and forth from Timmins every other month with a new, original solo album on CD. 


A few years later I started a band called the SALTCOATS which blended Jazz and Country by way of Folk music. We played a few Folk festivals, toured around Ontario, had a couple songs on the radio and won three songwriting awards between 2006-2009. I played with that band until I moved to Southern Ontario, where I reinvented myself again with a project that was part string quartet, part Jazz combo. It was my first time hearing my music with live strings, a cellist and a violinist. I called it "the Voice of my Soul" when I first heard that sound. I said it was like "Will Gillespie's Old World Romance," and that became our name.


Through a twist of fate that band metamorphosed into an Indie-Rock/Power-pop outfit called "Static & Snow," with a residency at the Supermarket in Toronto, NXNE and a couple other festivals under our belt. That band broke up and each went our separate ways. Finally I found myself in Hamilton, ON, on a blustery night in February at an open mic hosted by Dave Gould. It was at Homegrown Hamilton. And that was the beginning of my new phase in life as a solo artist with a band that combines all my former permutations and experiments into one sound, under one roof, under my name. 


Since moving to Hamilton I got back into working in Theatre as well as music. I wrote an original musical called "Swingin' in St. John's" that debuted at the Hamilton Fringe Festival in 2017. It won "Best of Venue: Hamilton Theatre Incorporated" as a 60-minute one-act play. That was the first show for my company “Chasing Shadows Productions.” We remounted the show for a two week run at Artword Artbar, (a local Cabaret space where I also played concerts) expanded into a 90-minute version with an intermission. We're currently mounting our third production of “Swingin’ in St. John’s” at the Burlington Performing Arts Centre’s Community Studio Theatre thanks to some funding from the BPAC/ACCOB Joint Community Studio Theatre Initiative. I debuted my second original musical comedy “Diamond in the Rough” at the 2019 Hamilton Fringe Festival, where that play won the Audience Choice award, out of 58 different shows from all over the world. Very honoured by that. We are lucky to have the same "dream cast" of actor-singers from "Diamond in the Rough” return for this latest production of “Swingin’ in St. John’s,” with plans to do a third new musical next Summer.


In the meantime, I have also put together a combo of musicians for my own "Will Gillespie Band" that bring my songs to life in ways I've only imagined before. Part Jazz combo, part Rock Band, part Palm-Court Classical Ensemble this collection of hired musicians takes my already full-sounding solo show from a black and white portrait into full-colour 3-D. I have finally found my sound.




There are three elements to a Will Gillespie show. He is a Songwriter, a Guitarist and an Entertainer. He distills his personal experiences into universal anthems or catchy little ditties, depending on the subject and then performs them with the same thoughtful care and craft, but made to look effortless. He’s just telling you a story, as much through his guitar and harmonica as with his words. These songs range from charming and whimsical to bombastic rockers to heart-breaking ballads, covering and criss-crossing several genres from Folk to Jazz, Cabaret, Waltzes, Blues and Rock & Roll.


Since moving to Hamilton, Ontario, Will has rekindled his love of theatre. He has written, directed and performed in two award-winning musicals in the last four years, with a third play due to debut this Summer. “Swingin’ in St. John’s” debuted at the 2017 Hamilton Fringe Festival and won “Best of Venue: Hamilton Theatre Incorporated” and was then remounted for two more productions in 2018 and 2019. Will’s second Musical “Diamond in the Rough” won the Audience Choice award out of 58 different shows from all around the world at the 2019 Hamilton Fringe Festival. This Summer he will debut “Martians & Martinis” a jazzy sci-fi romantic comedy musical, once again writing, directing, composing and performing.


Meanwhile, Will also writes, records and performs as a solo artist and fronting the Will Gillespie Band, telling his own story in his own voice. His new album “Change of Perspective” comes out in 2020.

Will Gillespie is a performer with a diverse and eclectic catalogue of original songs, exploring Folk, Rock & Roll, Cabaret and other styles. He is a one-man show, accompanying himself on guitar and harmonica but his main instrument is the heartstrings. It’s a surprisingly full sound for such minimal instrumentation.


Born and raised in South Porcupine, Northern Ontario, Will now calls Hamilton home. He brings this unique perspective to every performance, taking listeners with him from the small town to the big city, from the barn to the ballroom. Telling true stories beautifully through his lyrics, melody, voice, guitar and harmonica. 


Known for whimsical and exuberant performances of his thoughtfully crafted songs, Will Gillespie has been described as a "one-of-a-kind, finger-picking, old-time crooning, genuine songwriter you absolutely MUST see perform" 

- (Matt Thompson, The Stormalongs)


Equally expressive through clever lyrics, catchy, timeless melodies and evocative guitar playing, he takes the listener on an emotional journey with "the soul of a modern folk jazz troubadour...songs unfurl in the unadorned, unhurried way that is the mark of a true master artist..." 

- (Colin Gibson, Audio Reckoning)


"His music has the ability to speak deeply to absolutely ANYBODY" 

- (Jeremy Brazeau, Cambrian College)


Each Will Gillespie show is a unique experience. It has been said that he sounds like nothing you’ve ever heard before and like everything you’ve ever heard before. Sounds from every style of Popular Music from Folk to Jazz, Blues, Rock & Roll and World Music come to life together to tell these stories. Wide-ranging influences from across Canada’s Cultural Tapestry. Anything that captures the sound of the emotion.


Genuine, beautiful, classic entertainment.


"From songwriter to crooner and cabaret man to power pop genius, Will Gillespie is always evolving his artistry"

- (Paul Loewenberg, Former Artistic Director, Northern Lights Festival Boreal)