More About Jesse Roper
Jesse Roper is a modern-day troubadour; a Canadian artist defined by his authenticity and adventurous spirit; guitar in hand and a grin on his face.
Jesse, along with long-time bandmates the Pretty Good Band, has spent much of the last few years travelling the highways, byways and backroads of North America, bringing his own brand of modern, indie-infused Americana blues to fervent audiences across the continent. Known for his powerhouse live performances, Jesse is truly electrifying on stage - his soulful vocals expanding across silky guitars and hard-hitting grooves. You’d never guess that this soldier of the six string - all mischief, mayhem and virtuoso guitar playing - experienced crippling stage-fright long into his 20s. Today, the stage is his home and he’s inviting you in, cold one in hand, for one helluva good time.
Of course, he’s more than a magnetising stage presence and great hair - Jesse has the goods to back this up. A master at connecting his personal experiences to his songwriting, he crafts wildly entertaining narratives of the challenges and eccentricities of life, pulling inspiration from all that surrounds him. His musings on love (both won and lost), the call of the road and the promise of what's round the corner draw similarities to JJ Cale, Leon Bridges, and Alabama Shakes. His innate musical talent and flexibility of style have seen him play with soul icon Booker T. Jones, rock veteran Colin James, blues belter Beth Hart, and Canadian legend Burton Cummings. Across streaming platforms, he’s racked up over 500,000 monthly listeners and millions of streams.
While based in Victoria BC, Jesse is back on the road with the Pretty Good Band throughout 2026. All seasoned musicians themselves, the band is Matt Reid (bass), Chris Van Sickle (keys), East Coast Pete (guitar) and Brent Norman (drums). “Each one of these guys on their own is funnier and smarter than I am, but somehow I’m the band leader,” Jesse laughs. “I’m a lucky lead guy to have these cats in my band. They’re Pretty Good.”
For fans of: JJ Cale, Leon Bridges, Alabama Shakes, The Record Company, Nathaniel Rateliff, and blues-rock shows that feel better in the room than they ever could on paper.
Jesse, along with long-time bandmates the Pretty Good Band, has spent much of the last few years travelling the highways, byways and backroads of North America, bringing his own brand of modern, indie-infused Americana blues to fervent audiences across the continent. Known for his powerhouse live performances, Jesse is truly electrifying on stage - his soulful vocals expanding across silky guitars and hard-hitting grooves. You’d never guess that this soldier of the six string - all mischief, mayhem and virtuoso guitar playing - experienced crippling stage-fright long into his 20s. Today, the stage is his home and he’s inviting you in, cold one in hand, for one helluva good time.
Of course, he’s more than a magnetising stage presence and great hair - Jesse has the goods to back this up. A master at connecting his personal experiences to his songwriting, he crafts wildly entertaining narratives of the challenges and eccentricities of life, pulling inspiration from all that surrounds him. His musings on love (both won and lost), the call of the road and the promise of what's round the corner draw similarities to JJ Cale, Leon Bridges, and Alabama Shakes. His innate musical talent and flexibility of style have seen him play with soul icon Booker T. Jones, rock veteran Colin James, blues belter Beth Hart, and Canadian legend Burton Cummings. Across streaming platforms, he’s racked up over 500,000 monthly listeners and millions of streams.
While based in Victoria BC, Jesse is back on the road with the Pretty Good Band throughout 2026. All seasoned musicians themselves, the band is Matt Reid (bass), Chris Van Sickle (keys), East Coast Pete (guitar) and Brent Norman (drums). “Each one of these guys on their own is funnier and smarter than I am, but somehow I’m the band leader,” Jesse laughs. “I’m a lucky lead guy to have these cats in my band. They’re Pretty Good.”
For fans of: JJ Cale, Leon Bridges, Alabama Shakes, The Record Company, Nathaniel Rateliff, and blues-rock shows that feel better in the room than they ever could on paper.
Date & Time
November 18, 2026
7:00pm - 11:00pm
Location
StageOne
70 Sanford Street
Fairfield, CT 06824
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The Fairfield Theatre Company is a nonprofit center for the arts and culture located in the heart of downtown Fairfield, Connecticut. We bring together a community of musicians, actors, artists, writers, fans, and supporters who are dedicated to the simple premise that the broadest spectrum of live entertainment and cultural exchange is essential to the vitality of our society.
We believe that our quality of life is richly influenced by opportunities to get out and come together in public places to enjoy art, music, theatre, film, arts education and all manner of creative and intellectual discourse, and to participate in these activities to the fullest. To that end, we work diligently to establish and sustain venues for the presentation of concerts, plays, films, visual arts, and arts education. We seek to appeal to the most diverse audience possible, as often as we possibly can. We endeavor to strengthen our community and nurture, enrich, and enlighten the lives of those we touch. Our hope is to make our world a better place one great performance at a time.
We believe that our quality of life is richly influenced by opportunities to get out and come together in public places to enjoy art, music, theatre, film, arts education and all manner of creative and intellectual discourse, and to participate in these activities to the fullest. To that end, we work diligently to establish and sustain venues for the presentation of concerts, plays, films, visual arts, and arts education. We seek to appeal to the most diverse audience possible, as often as we possibly can. We endeavor to strengthen our community and nurture, enrich, and enlighten the lives of those we touch. Our hope is to make our world a better place one great performance at a time.
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